JEE Sprint Chemistry

IUPAC Nomenclature
SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER)
1. IUPAC name of the hydrocarbon (A) is :
CH3

A:
C2H5
(A) 2-ethyl-5methylhexane (B) 5-ethyl-2methylhexane
(C) 2, 5-dimethylheptane (D) 5-ethyl-2,5-dimethylpentane
2. IUPAC name of neopentyl group is :
(A) 2,2-dimethylbutyl (B) 2, 2-dimethylpropyl (C) 1, 1-dimethylbutyl (D) 1, 1-dimethylpropyl
3. IUPAC name of the following compouund is :
OH
CH3

(A) 2-methyl-3-cyclohexenol (B) 3-methyl-1-cyclohexen-4-ol

(C) 4-hydroxy-3-methyl-1-cyclohexene (D) 2-hydroxy-1-methylcyclohexene
4. Which compound is tertiary alcohol ?
(A) 1-propanol (B) 2-methyl-1-hexanol (C) 3-methyl-2-hexanol (D) 2-methyl-2-hexanol
5. 3-Butenoic acid (or But-3-enoic acid) is represented as :

O O O
(A) (B) (C) (D) none of these
OH OH OH

OH

6. In the nomenclature of priority order is –

CH3

(A) –CH3 < –OH < C=C (first) (B) –OH<–CH 3 < C=C (first)
(C) C=C<–CH 3 <–OH (first) (D) –CH3 < C=C < – OH (first)
7. C 4 H 8 O 2 represents :-
(A) An acid only (B) An ester only
(C) An ketone only (D) An acid and an ester also
8. The higher homologue of dimethylamine (CH 3 —NH—CH 3 ) has the structure :-
(A) (CH 3 ) 3 N (B) CH 3 —CH 2 —CH 2 —NH 2

(C) CH 3 —NH—CH 2 —CH 3 (D) CH3 CH CH3

NH2

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9. The third member of the family of alkenynes has the molecular formula :-
(A) C 3 H 2 (B) C 5 H 6 (C) C 6 H 8 (D) C 4 H 4
10. The hetero atoms present in the following compound is/are :

NH2

(A) 2 (B) 3 (C) 1 (D) 4

11. Which of the following have only 2° H-atom :

CH3 CH2
(a) (b) (c) (d)

Correct code is :
(A) only a and b (B) a, b and d (C) a, c and d (D) All of them
12. Common name of CH 2 CH—CN is :-
(a) acrylonitrile (b) vinyl cyanide
(c) allyl cyanide (d) allyl nitrile
(A) a, b and d (B) a and b (C) only b (D) a, b and c
13. Which of the following names is correct :-
(A) 4–Isopropyl–3–methyl hexane (B) 2–Ethyl–3–isopropyl pentane
(C) 3–Isopropyl–4–methyl hexane (D) 3–Ethyl–2,4–dimethyl hexane
14. The correct systematic IUPAC name of the given compound is :

OH
CH2 C CH2 C OH
COOHCOOH O

(A) 3–Carboxy–3–hydroxy butane dioic acid (B) 2–Hydroxy propane–1,2,3–tricarboxylic acid

(C) 3–Hydroxy butane dioic acid (D) 2–Bis(carboxymethyl)–2–hydroxy ethanoic acid
15. T he IUPAC name of CH 3 —CH 2 —NH—CH 3 is :-
(A) Methyl ethyl amine (B) 1–methyl amino ethane
(C) N–methyl ethanamine (D) N–ethyl methanamine
16. The correct IUPAC name from the incorrect name 4–Amino–3–hydroxy–2–butene is :-
(A) 1–Amino–2–hydroxy–2–butene (B) 4–Amino–2–buten–3–ol
(C) 1–Amino–2–buten–2–ol (D) 1–Amino–2–butenol
17. The correct name of 2–chlorobutan–3–ol is :-
(A) 3–Chloro–2–hydroxy butane (B) 3–Chloro–2–butanol
(C) 3–Hydroxy–2–chloro butane (D) 2–Chloro–3–hydroxy butane

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H
18. The correct name for C O is :-
OH
(A) 2–Hydroxy cyclopentanal (B) 2–Formyl–1–hydroxy cyclopentane
(C) 2–Hydroxy cyclopentane carbaldehyde (D) Cyclopentane–2–ol–1–al

CH2 CH2
19. The name for the structure H2C CH C Cl
CH2 CH2
O
(A) Cyclo hexanoyl chloride (B) Cyclohexane carbonyl chloride
(C) 1–Chloro cyclohexanal (D) Chloro cyclohexyl methanal

20. CH3 O C CH2 COOH

O
The correct IUPAC name of the above compound is :
(A) 2–Acetoxy ethanoic acid (B) 2–Methoxycarbonyl ethanoic acid
(C) 3–Methoxyformyl ethanoic acid (D) 2–Methoxyformyl acetic acid

ANSWER KEY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans . C B A D A D D C C A B B D B C
Qu e. 16 17 18 19 20
Ans . C B C B B

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GOC
SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER)
1. Carbanion is a :-
(A) Base (B) Nucleophile (C) Both (A) and (B) (D) None
2. Electrophile is :
(A) H 2O (B) NH 3 (C) AlCl 3 (D) C 2 H 5NH 2
3. Which of the following species has a pyramidal shape-

(A) CH 3 + (B) BF3 (C) CH 3– (D) C H 3
4. Increasing order (least basic first) of basic strength is shown by the set
(A) ClNH 2 , NH 3 , CH 3 NH 2 (B) ClNH 2 , CH 3 NH 2 , NH 3
(C) NH 3 , ClNH 2 , CH 3 NH 2 (D) CH 3 NH 2 , ClNH 2 , NH 3
5. The decreasing order of acid strength indicated by the following sequence of reaction is :-

NaNH2   C2H2 H2O

–C–H –C–Na HC CNa+ Ph3CH HC CH + NaOH

(A) NH 3 > Ph 3 CH > C 2 H 2 > H 2 O (B) H 2 O > HC  CH > Ph 3 CH > NH 3

(C) HC  CH > H 2 O > Ph 3 CH > NH 3 (D) Ph 3 CH > HC  CH > H 2 O > NH 3

6. In which of the following compounds is hydroxylic proton the most acidic -

F O O
I O
(A) O (B) (C) H (D) H
H H F F
7. Correct arrangement of the following acids in correct Ka order is :-

(I) H 3 N  —CH 2 —COOH (II) NC—CH 2 —COOH (III) H 3 C—CH 2 —COOH (IV) OOC —CH 2 —COOH
(A) I > II > III > IV (B) II > I > III > IV (C) I > III > II > IV (D) IV > III > II > I
8. Which of the following orders of acid strength is correct :-
(A) RCOOH > ROH > HOH > HC CH (B) RCOOH > HOH > ROH > HC CH
(C) RCOOH > HOH > HC CH > ROH (D) RCOOH > HC CH > HOH > ROH
9. Which of them is false for order of – I effect
 
(A) –F > –Cl > –Br > I (B) –NR3 > –NH3 > –NO2

(C) –OCH3 > –OH > –NH 2 (D) > –C  CH > H

10. The order of basicity of halides is :

– – – – – –
(A) Cl < Br – < I < F (B) F < I < Br– < Cl
– – – – – –
(C) I < Br – < Cl < F (D) Cl < F < I < Br –

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11. Which of the following molecule has longest C=C bond length -

(A) CH 2 =C=CH 2 (B) CH 3 –CH=CH 2

CH3
(C) CH3–C–CH=CH2 (D) CH3–C=CH2
CH3 CH3
H 3O 
12. In the reaction CH 3CN  CH 3COOH
heat

the hybridization state of the functional carbon changes from

(A) sp3 to sp2 (B) sp2 to sp3 (C) sp to sp2 (D) sp2 to sp
13. Most stable carbocation is :-

   
CH2 CH2 CH2 CH2

(A) (B) (C) (D)

Cl NO2 OCH3

14. Most stable carbanion is :-

(A) HC C (B) C 6 H 5 (C) (CH 3 ) 3 C—CH 2 (D) (CH 3 ) 2C CH 
15. Consider the following carbocations

   
(a) CH3O– –CH2 (b) –CH2 (c) CH3– –CH2 (d) CH 3— C H 2

The relative stabilities of these carbocations are such that :-

(A) d < b < c < a (B) b < d < c < a
(C) d < b < a < c (D) b < d < a < c
16. Among the following, the strongest base is :-
(A) C 6 H 5 NH 2 (B) p–NO 2 –C 6 H 4 NH 2 (C) m–NO 2 –C 6 H 4 NH 2 (D) C 6 H 5 CH 2 NH 2

17. The increasing order of base strength of Cl –, CH 3 COO – , —

OH and F — is :
(A) Cl – < F — < CH 3 COO – < —
OH (B) Cl – > F — > CH 3 COO – > —
OH
– – — —
(C) CH 3 COO < Cl < F < OH (D) None of these
18. Formic acid is considered as a hybrid of the four structures


O O O O

H– C–OH  H– C = O H  H–C–O–H  H–C–O–H
 

I II III IV
Which of the following order is correct for the stability of the four contributing structures.
(A) I > II > III > IV (B) I > II > IV > III (C) I > III > II > IV (D) I > IV > III > II
19. Which of the following carbonium ion is most stable
(A) Ph 3 C + (B) (CH 3 ) 3 C + (C) (CH 3 ) 2 CH + (D) CH 2 CH—CH 2+

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20. Among the following the aromatic compound is

(A) (B) (C) (D)

  

21. Match List- I with List- II and select the correct answer using the codes given below -
List-I (Stability) List -II (Reason)

H3C CH3
C
(A) > CH 3+ (1) Inductive effect

 Br
(B) H3C–C < CH3– (2) Resonance
CH3

 CH3
(C) H3C–C > H 3C–CH 2+ (3) Hyperconjugation and resonance
CH3

• H3C •
CH2 CH2
(D) > CH3 (4) Hyperconjugation and inductive effect

Codes :
(A) A - 2 ; B - 3 ; C - 4 ; D - 1 (B) A - 3 ; B - 1 ; C - 4 ; D -2
(C) A - 4 ; B - 3 ; C - 1 ; D - 2 (D) A - 3 ; B - 4 ; C - 2 ; D - 1
22. Which of the following compounds is the strongest base -

(A) NH2 (B) NH2 (C) CH3 NH2 (D) NHCOCH3

23. In which of the following molecule all the effect namely inductive, mesomeric & hyperconjugation operate:

(A) —Cl (B) —CH3 (C) —COCH3 (D)

CH3 CH3

24. Which of the following reaction is possible :

OH ONa

(A) + (B) CH3–C–OH + HCOONa

O
NO2

SO3Na COOH

(C) + (D) H–CC–Na+H 2 O 

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COOH

25. , pK a value of the compound decreases if X is :-

(A) –NO 2 (B) –NH 2 (C) –OH (D) –OCH 3

26. Which one of the following results most stable carbon free radical :
• •
CH3 CH3
(A) (B)

• •
(C) (Ph) 2C = C(Ph) 2 CH3 (D) CH 2 = CH 2 CH3

H

CH3–C–CH2
1,2 shift
27. A (Major) ; Here A is :

CH3
 
CH3–C–CH3 CH–CH2
(A) (B)

H
(C) CH3–C–H2C– (D) CH3–C= CH2

Ph

28. –CH2OH ; On dehydration with conc. H2SO4 forms predominantly :

(A) =CH2 (B) –CH3 (C) –CH3 (D) –CH3

29. Which of the following is incorrect :

CH2CH3 •CHCH3

•
:O 
O O O
Cl + HCl
(A) (B) HO–C–H+ C–H  HO–C–H + H–C–H
H H H

H–CH2 H
   
H shift –
(C) CH3 –C  CH3 –C–CH2 HO
(D) CH 3 CH 2 CHO   CH 3 C HCHO  H 2 O
CH3 H

30. The Ka values of alcohols, water and phenol are of order 10–17, 10–14 and 10–10 respectively. Which of the
following reactions is possible :
(I) C 6 H 5 O  + H 2 O  C 6 H 5 OH + OH  (II) C 2H 5 O  + H 2O  C 6 H 5 OH + OH 
(A) Both I and II (B) only II (C) only I (D) neither of two

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31. Most stable carbanion is :

 
CH2 CH2

(A) CH 3 (B) CH 2  CH – CH 2 (C) (D)

NO2
32. Stability of :

CH3
(I) C H 3 – C H = C H – C H 3 (II) CH3– C = C – CH3 (III) CH3– C = CH2 (IV) CH3– C = CH – CH3
CH3 CH3 CH3

in the increasing order is :

(A) I < III < IV < II (B) I < II < III < IV (C) I < IV < III < I (D) II < III < IV < I

H2O
33. –MgBr + CH2—CH2 [A] ; the product (A) is :
O

(A) –CH2OH (B) –CH2CH2OH

(C) —CH—CH2 (D) No reaction

O

34. Spin multiplicity of Triplet nitrene is :

(A) 1 (B) 2 (C) 3 (D) 4
35. The maximum probability of proton loss is in the case of :

H H
  H 
(A) CH 3 – CH 2 (B) CH3– C – CH3 (C) (D) (CH3)2C – CH2
CH3 

36. Select the least stable one :

H3C H3C 

(A) CH3 – CH2 
(B) CH3– CH2– CH2 (C) CH– CH2 (D) 3C C – CH2
H
H3C H3C

37. Which of the following will react fastest with conc. HCl :

(A) –CH2CH2OH (B) –CH(OH)CH3

(C) –OH (D) –CH2OH

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38. Consider the following reaction :

OCH3

+ NaNH2 Product
Br
The product (P) and reaction (R) are :

OCH3 OCH3
NH2 NH2
(A) ; addition-elimination (B) ; elimination addition

OCH3 OCH3

(C) ; elimination addition (D) ; cine substitution

NH2 NH2

39. Energy of activation is lower for which reaction :

   
(A) RCH 2 OH 2  R C H 2 (B) R 2 CH OH 2  R 2 C H
 
(C) R 3 C OH 2  R 3 C (D) all have same E act.

ANSWER KEY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans . C C C A B D A B D C D C C A A
Qu e. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans . D A A A A B B C D A C A B C B
Qu e. 31 32 33 34 35 36 37 38 39
Ans . D A B C C D B C C

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Level-2
SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS)
1. The correct order of decreasing basic strength is :

NH2

N N N
H H
I II III IV
(A) I > II > III > IV (B) II > III > I > IV (C) II > IV > I > III (D) II > III > IV > I
2. The correct order of increasing dissociation constant of the following compound is :-

OH OH OH OH
NO2 NO2 NO2

NO2
NO2
NO2 NO2

I II III IV
(A) II < IV < I < III (B) IV < III < I < II (C) IV < II < I < III (D) IV < I < II < III
3. In the following arrange the H (numbered) for their ease of displacement during acid base reaction :
(2)
(3) OH
HO
H NaNH2(liquid NH3)
(1) 2 equivalent

(A) 1 > 2 > 3 (B) 3 > 2 > 1 (C) 3 > 1 > 2 (D) 2 > 3 > 1
4. Which one of the following is the strongest base in aqueous medium :-
(A) (C 2 H 5 ) 3 N (B) C 2 H 5 NH 2 (C) NH 3 (D) (C 2 H 5 ) 2 NH
5. The correct order of acid strength of the following compound is -

(I) CH3–C–CH3 (II) CH3–C–C–CH3 (III) CH3–C–CH2–C–CH3

O OO O O
(A) III > II > I (B) III > I > II (C) II > I > III (D) I > II > III
6. Which of the following shows the correct order of decreasing basicity in aqueous medium -
(A) (CH 3 ) 3 N > (CH 3 ) 2 NH > CH 3 NH 2 > NH 3 (B) (CH 3 ) 2 NH > (CH 3 ) 3 N > CH 3 NH 2 > NH 3
(C) (CH 3 ) 2 NH > CH 3 NH 2 > (CH 3 ) 3 N > NH 3 (D) (CH 3 ) 2 NH > CH 3 NH 2 > NH 3 > (CH 3 ) 3 N
7. For the compounds

N N N

H H
I II III
the order of basicity is -
(A) III > II > I (B) II > III > I (C) I > II > III (D) II > I > III

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8. Which of the following shows the correct order of decreasing acidity-
(A) PhCO 2 H > PhSO 3 H > PhCH 2 OH > PhOH
(B) PhSO 3 H > PhOH > PhCO 2 H > PhCH 2 OH
(C) PhCO 2 H > PhOH > PhCH 2 OH > PhSO 3 H
(D) PhSO 3 H > PhCO 2 H > PhOH > PhCH 2 OH
7 9. Give the correct order of increasing acidity of the following compounds-

OH OH COOH CCH

I II III IV
(A) II < I < III < IV (B) IV < II < I < III (C) I < II < IV < III (D) IV < I < II < III
10. Which of the following is the most acidic
(A) CH 2 = CH 2 (B) HC  CH

(C) CH 2 =CHCH 2 CH=CH 2 (D)

11. Which of the following substituents will increase the acidity of phenol -
(A) –NO 2 (B) –CN (C) –CHO (D) – CH 3

12. (I) (II) (III)

Compare carbon-carbon bond rotation across I, II, III.

(A) I > II > III (B) I > III > II (C) II > I > III (D) II > III > I
13. Which of the following s-bonds participate in hyperconjugation :

I V
H
H CH3
II
H IV
III
(A) I and II (B) I and V (C) I and V (D) III and IV

14. NH, N–H, N

O
(x) (y) (z)

The correct order of decreasing basic strengths of x, y and z is :

(A) x > y > z (B) x > z > y (C) y > x > z (D) y > z > x

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15. Set the following in increasing order of their p K a values:

O O

(x) CH3—S—O—H (y) CH3—C—O—H (z) CH3—OH

O
(A) y > x > z (B) x < y < z (C) y > z > x (D) x < z < y
16. Rank the following alkenes in order of decreasing heats of hydrogenation (largest first):

(I) (II) (III) (IV)

(A) II > III > IV > I (B) II > IV > III > I (C) I > III > IV > II (D) I > IV > III > II
17. Which of the following molecules has all the effects : inductive, mesomeric and Baker Nathan effect ?
(A) C 2 H 5 Cl (B) CH 3 –CH=CH 2

(C) CH 2 =CH–CH=CH 2 (D) CH 3 –CH=CH –C–CH 3

O

18. Which nitorgen in LSD (Lysergic acid diethylamide) is more basic :

O
I III
H–N –C–N(C2H5)2
II
N
CH3
(A) I (B) II (C) III (D) all are equally basic
19. Which of the following substituted carboxylic acids has the highest K a value :

(A) CH 3 —CH 2 —CH— COOH (B) CH 3 —CH— CH 2 —COOH

Cl Cl
(C) CH2— CH 2 —CH 2 —COOH (D) CH 3 —CH— CH 2 —COOH
Cl Br
SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS)

20. Which of the following compounds yield most stable carbanion after rupture of (C 1 –C 2 ) bond :

O O
(A) CH3—C—CCl3 (B) CH3—C—CBr3
1 2 1 2

O
(C) CH3—CH2—C—CI3 (D) None of these
1 2

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N N
21.
H NH2
pyrrole (I) pyridine (II) aniline (III)

Which is/are correct statements ?

(A) I is more basic than II (B) II is more basic than I and III
(C) III is more basic than II (D) all are aromatic bases
22. Following is true for stability between the two structures :


O O
(A) CH3–CH–CH=CH2 > CH3–C=CH–CH3

CH2
•
(B) CH 2=CH–CH=CH–CH 2• > CH2–C–CH–CH3

CH3
 
(C) CH2=C–CH2 > CH 3 –CH=CH– CH 2

O

(D) —O < CH3–C–O

23. Which have acidic hydrogen :

O
(A) CH 3 COOH (B) —OH (C) CH3—C—CH2—CN (D) NaNH2

24. C—C and C=C bond lengths are unequal in :

(A) Benzene (B) 1,3 buta-di-ene
(C) 1, 3 cyclohexa-di-ene (D) None
25. The acid strength of substituted carboxylic acids is known to be dependent on the nature and position of
the substituent. In the following examples, an attempt has been made to arrange the acids in order of acid
strength, the strongest first. One of the series is incorrect-which one :
(A) CH 3 .CH 2 CH(Cl).COOH > CH 3 .CH(Cl).CH 2 COOH > CH 3 .CH 2 .CH 2 .COOH
(B) NO 2 .CH 2 .COOH > HOCH 2 . COOH > CH 3 .COOH
(C) Cl 3 C.COOH > BrCH 2 .COOH > FCH 2 .COOH
(D) CH 3 . COOH > CH 3 .CH 2 .COOH > (CH 3 ) 3 C.COOH
26. Which species is not aromatic :

(A) (B) (C) NH (D)

N N
:

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27. Select the correct option :
(A) carbonic acid is weaker acid than acetic acid
(B) the boiling points of acids are higher than corresponding alcohols
(C) chloroacetic acid is stronger acid than acetic acid
(D) phenol is more acidic than ethanol
28. Which reacts with AgNO 3 to give ppt. :

—Br
(A) —Br (B) –CH=CH–CH2Br (C) (D) —Br

29. Which statement is ture :

– –
(A) NH2
is stronger base than OH

(B) NH 2–OH is less basic than NH 3

(C) CH 3 –NH 2 is weaker base than N(CH 3 ) 3 in (aq) medium

NH2 CH2–NH2

(D) is weaker base than

30. Which is less acidic than phenol :

OH OH

—CH3 —NH2
(A) (B) CH 3 –OH (C) (D) H 2 O

31. The precursor carbocation to the product in the following reaction is :

H

C6H5 H C6H5
OH H


(A) C6H5 (B) C6H5  (C) either of the two (D) none of the two

32. Which of the following ion is formed in the following reaction :

H
OH O



(A) 
(B)
OH OH


CH2
(C) (D) All of three
OH

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OD
D NaOH
33. [Intermediate] P. Product is :
CO2 D

OD OD
HOOC D DOOC D
(A) (B)

OH
DOOC D
(C) (D) Reaction not possible

34. Predict the nature of A in the following reaction :

O
+ ClCH2COOC2H5 Base
(A)

Cl
O
CCOOC2H5
(A) (B)
CH2COOC2H5

O O
(C) CHCOOC2H5 (D) CHCOOC2H5

35. Which of the following intermediate is most likely to be formed during addition of HBr on crotonic acid :

CH 3 CH = CHCOOH + HBr(g)  CH 3 CH–CH 2 COOH :

Br
 
(A) CH 3 CH 2 – C HCOOH (B) CH 3 CH – CH 2COOH
OH
(C) CH3CH=CH–C–OH (D) none of these


36. Which will give most stable cation upon strong heating :

CH2–Cl Cl
CH2
(A) (B) (Ph) 3C–Cl (C) (D) CH
CH2–Cl

Cl
37. (A); Here (A) is :
—Cl
H


(A) (B) (C) 

(D)



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 JEE Sprint Chemistry

F

–F
38. Cl – C – C – F [X] ; Here [X] is :
Cl F

F F F F
(A) Cl – C = C – F (B) Cl – C = C – Cl (C) Cl – C = C – F (D) C l – C = C – F
Cl F Cl F

H3C CH3
H3C CH3 CHCl3
C C KOH
39. H H the reaction proceeds via :
H H

(A) carbene (B) Carbon free radical (C) Carbocation (D) Carbanion

Cl
:C Cl
40. (A) ; Here A is :
••
N
H
Cl
Cl
(A) (B) Cl
 (C) (D)
N N N
N
H
41. Which of the following can give benzyne :

Cl Cl
(A) NaNH2 (B)  (C) NaNH2 (D) All
H N2 Br

42. Dehydration of the following in increasing order is :

(I) –OH (II) –OH (III) –OH (IV) –OH

(A) I < II < III < IV (B) II < III < IV < I (C) I < III < IV < II (D) I < IV < II < III
43. Increasing tendency for SN1 and SN2 reaction is :

CH3
(I) CH 3 CH 2 CH 2 CH 2 Cl (II) CH3CH2CH – CH3 (III) CH3CHCH2 – Cl (IV) CH3–C – Cl
Cl CH3 CH3

(A) SN1 ; I < III < II < I V (B) SN2 ; IV < II < III < I
(C) (A) and (B) both are correct (D) Both incorrect
44. Cyclopentyl ethyl ether can be obtained by :

(A) –ONa+CH3CH2Br (B) –Br+CHCH

3 2ONa

(C) –OH+CH3CH2Cl (D) none is correct

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 JEE Sprint Chemistry

45. Major product in the following reaction is :

–Br + KOCH2CH3 Product

(A) –OCH2CH3 (B) (C) —Br (D)

OCH2CH3

46. Mechanism of insertion reaction is of :

(A) One step for triplet carbene (B) Two step for singlet carbene
(C) One step for singlet carbene (D) Two step for both
H3C
1 
6 2 NH2
47. (P) . The most probable structure of intermediate P is :
5 –Cl
3
4

OCH3 OCH3 OCH3 OCH3

1 1 1 1
6 2 6 2 6 2 6 2
(A) (B) (C) (D)
5 3 5 3 5 3 5 3
4 4 4 4

CH3
1 
6 2 NH2
48. (A) . The most probable structure of intermediate A is :
5 –Cl
3
4

CH3 CH3 CH3 CH3

1 1 1 1
6 2 6 2 6 2 6 2
(A) (B) (C) (D)
5 3 5 3 5 3 5 3
4 4 4 4

49. Hybridisation of arrow headed 'C' is

(A) sp 2 sp 3 (B) sp 3 sp 3 (C) sp 2 sp 2 (D) sp 3 sp 3 d

50. Which of the following is most strongest electrophile :

•• ••
(A) singlet H – N
•
• (B) triplet H – N
•
• (C) singlet –C (D) triplet –C–

51. In benzyne two external unshared electronic orbital :

(A) do not overlap to form a  bond (B) can overlap to form a complete  bond
(C) poorly overlap to form a ver y weak bond (D) contribute in benzene ring
52. Which of the following is aromatic intermediate :

•
•
(A) carbene (B) (C) Benzyne (D)
•

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 JEE Sprint Chemistry

53. In which of the following case 'H' shift is more preferable than 'CH 3 ' shift :

CH3 CH3 H
 
(A) CH3–C–CH2 (B) CH3–C– CH–C–H
H CH3 H

CH3

(C) CH3–C–CH–CH3 (D) all
Ph

54. Which of the following will not give 1, 2, shift :

2
Hg

OH
(A) (CH 3 )3 C — C H 2 (B) (CH3)3C CH—CH2 (C) 
(D) all

55. Which of the following reactions is wrong :

 
(A) CH3CH2CHO OH
CH3 – CH – CHO

•
CH2CH3 CHCH3 + HCl
(B) Cl•

O O O O
(C) HO–C–H+ H– C–H  HO– C–H + H–C–H
H H

CH3
(D) CH3 –C 
Hydride
shifting
CH3 –CH–CH2
CH3 CH3

56. Methyl benzylic carbonium ion is the most stable one, hence it will react fastest consider the following
reaction :
Br CH3 SN2
+ OH (P) ; product (P) will be :
H H

H CH3 HO CH3
(A) (B)
HO H H H

OH
H CH3 CH3
H
(C) (D)
H H H H
OH

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 JEE Sprint Chemistry
57. Consider the following reaction -
R – CH = CH2+ IN3  A , A is :

(A) R – CH – CH2N3 (B) R – CH – CH2I

I N3

(C) R – CH – CH2 (D) R – CH– CH

N N
I

58. + CHBr3 1 BuOK product ; product will be :

Br Br Br
(A) Br (B) Br
Br

Br
(C) (D)
Br

CH2

59. HBr major product will be :

Me CH2Br CH2Br CH3

Br
(A) (B) (C) (D)
Br

CH3
O OH
60.  Product ; major product of the reaction can be :
O
CH3

O O O O

(A) (B) (C) (D)

( i ) Zn
61. CH3COCH3 + BrCH2COOEt 
( ii ) H 2 O / H 
 (A) ; the product (A) is :

OCH3 OH
CH3
(A) C (B) CH3–C–CH2COOEt
CH3 Br
CH3

CH3 OH CH3 OCH2COOEt

(C) C (D) C
CH3 COOEt CH3 Br

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 JEE Sprint Chemistry

OH

62. Which carbocation is more likely to be formed in the dehydration of H :


 
(A) (B) (C) (D)


63. The most probable structure for (P) in the following reaction is :

conc H2SO4
2 (P)

(A) (B) (C) (D)

64. Which of the following alcohols is dehydrated most readily with conc. H2SO4 ?

CHOHCH3 CHOHCH3 CHOHCH3 CHOHCH3

(A) (B) (C) (D)

OCH3 NO2 Cl

65. Dehydration of alcohols by conc. H2SO4 takes palce according to following steps :

CH3 CH3 CH3

•• H  –H2O 
CH3–C–CHOH
2 •• step -I CH3–C–CHOH
2 2 step -II CH3–C–CH2
H H H


CH3 CH3
1,2–H shift –H
step -III CH3–C–CH3 step -IV CH2=C–CH3


the slowest and fastest steps in the above reaction are :

(A) step I is slowest, while III is fastest
(B) step II is slowest, while III is fastest
(C) step II is slowest, while IV is fastest
(D) all step proceed at equal rate

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 JEE Sprint Chemistry

66. Pyrrole is treated with alkaline chloroform to form two products A and B ?

Cl
+ CHCl3 KOH +
N N CHO N
H H
(A) (B)

Which of the following intermediate is likely to be formed ?

Cl
C 
H Cl
(I)  (II)  (III) ••
(IV)
N CCl2 N N N
H
(A) I and IV (B) I and III (C) III and IV (D) I, III and IV

conc. H2SO4
67. Major product is :

OH

(A) (B) (C) (D)

ANSWER KEY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans . D C B D A C D D B D A ,B,C C B B B
Qu e. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans . D D B A A B,D A ,C A ,B,C C C B A ,B,C ,D B,D A ,D A ,B,D
Qu e. 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
Ans . A B C D C C C A A D D A A A B
Qu e. 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
Ans . C A B C B C C A B D A B C A B
Qu e. 61 62 63 64 65 66 67
Ans . B C C B C B C

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 JEE Sprint Chemistry
Isomerism
SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER)
1. Type of isomerism exists between :-

CH 3 —CH 2 —CH 2 —CN and CH3 CH CH3

CN

(A) Position (B) Chain (C) Both the above (D) None of these
2. The number of primar y alcohols possible with the formula C 4 H 10 O is -
(A) 2 (B) 3 (C) 4 (D) 5
3. The total number of benzene derivatives having the molecular formula C 7 H 7Cl is -
(A) 2 (B) 3 (C) 4 (D) 5
4. Which of the following will lead to maximum enolisation :–
(A) CH 3 COCH 3 (B) CH 3 COCH 2 CHO

O
(C) CH3 C CH C CH3 (D)
O Br O

H3C H
C C H
5. H3C C Exhibits :-
H3C COOH

(A) Tautomerism (B) Optical isomerism

(C) Geometrical isomerism (D) Geometrical and optical isomerism
6. Tautomerism is not exhibited by :-

(A) (B) (CH 3 ) 2 CHNO 2

(C) (D) (CH 3 ) 3 CCHO

7. Given compound exhibits x geometrical isomers and y optical isomers

The value of x and y respectively are :-

(A) 4 and 4 (B) 2 and 2 (C) 2 and 4 (D) 4 and 2
8. The total number of cyclic compounds (neglecting stereoisomers) with the molecular formula C 5H 10 is -
(A) 4 (B) 5 (C) 6 (D) 7
9. Which of the following exhibits tautomerism ?
(A) (CH 3 ) 2 NH (B) (CH 3 ) 3 CNO 2 (C) R 3 CNO 2 (D) RCH 2 NO 2

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 JEE Sprint Chemistry
10. The correct structure of trans–2–hexenal is -

(A) CHO (B)

CHO

(C) (D) CHO

CHO
11. The total number of benzene derivatives having the molecular formula C 7 H 8 O is -
(A) 3 (B) 4 (C) 5 (D) 6
12. Which of the following compounds does not exhibit tautomerism
(A) CH 3 NO 2 (B) CH 3 CH 2 NO 2
(C) C 6 H 5 CH=CH–OH (D) CH 3 CH 2 OH
13. The total number of benzene derivatives with the molecular formula C 6H 3 Cl 3 is -
(A) 2 (B) 3 (C) 4 (D) 5
14. Which of the following compounds is not chiral ?
(A) DCH 2 CH 2 CH 2 Cl (B) CH 3 CHDCH 2 Cl (C) CH 3 CHClCH 2 D (D) CH 3 CH 2 CHDCl

15. The total number of stereoisomers of 2,3–dibromobutane is -

(A) 2 (B) 3 (C) 4 (D) 5
16. In the structure :

CH3
H OH
H Br the configurations at the chiral centres are :
CH3
(A) 2R, 3R (B) 2S, 3R (C) 2R, 3S (D) 2S, 3S
17. Which of the following compound contains a pseudo-asymmetric carbon atom

(A) CH3CHCHCH2 (B) CH3CH–CH–CHCH3

Br Br Br Br OH Br

(C) CH3CHCHCHCH3 (D) CH3CHCHCHCH3

OHBr Br Br OHCl
18. Consider the following structures (A), (B), (C) and (D) -

CH3 C2H5

(A) Cl Br (B) Cl Br

C2H5 CH3

Cl Cl
(C) CH3 Br (D) C2H5 CH3
C2H5 Br
Which of the following statements is not correct
(A) B and C are identical (B) A and B are enantiomers
(C) A and C are enantiomers (D) B and D are enantiomers

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 JEE Sprint Chemistry
19. The interchange of two groups (Br and CH 3) at the chiral centre of the projection formula (A) yields the
formula (B), while the interchange of another set of two groups (C2H5 and Cl) of (A) yields the projection
formula (C) -

CH3 Br CH3

Cl Br Cl CH3 C2H5 Br

C2H5 C2H5 Cl
(A) (B) (C)
Which of the following statements is not correct about the structures (A), (B) and (C) -
(A) B and C are identical (B) A and C are enantiomers
(C) B and C are enantiomers (D) A and B are enantiomers
20. How many meso stereoisomers are possible for 2, 3, 4-pentanetriol -
(A) 1 (B) 2 (C) 3 (D) none of these
21. The total number of stereoisomers of the compound

CH3CH=CH–CH–CH=CH–CH3 is -
OH

(A) 2 (B) 3 (C) 4 (D) 8

22. The total number of aldehydes and ketones with the molecular formula C 4 H 8O is -
(A) 2 (B) 3 (C) 4 (D) 5
23. In which of the following properties do enantiomers differ from each other
(A) Solubility in an achiral solvent (B) Reactivity with an achiral reagent
(C) Melting point (D) Optical rotation
24. (+) - Mandelic acid has a specific rotation of + 158º. What would be the observed specific rotation of a
mixture of 25% (–) -mandelic acid and 75% (+) -mandelidc acid :
(A) + 118.5° (B) –118.5° (C) – 79° (D) + 79°
25. When C 6H 4Cl 2 is converted into C 6H 3Cl 3, o-isomer will give m types of C 6H 3Cl 3, and p-isomer will give
q types of C 6 H 3 Cl 3. m, n, q are respectively :
(A) 1, 2, 3 (B) 2, 1, 3 (C) 1, 3, 2 (D) 2, 3, 1

ANSWER KEY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
An s . B A C D B D B A D B C D B A B B B D C D
Qu e. 21 22 23 24 25
An s . C B B D B

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 JEE Sprint Chemistry
Level-2
SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS)

1. Tautomerism is shown by :-
O O
(A) HCN (B) CH3—C—CH2—C—CH3

O
(C) CH3—CH2—N (D) CCl 3 CHO
O
2. In which of the following cases, cis-trans nomenclature can not be used :-
(A) Cl—CH=CH—Cl (B) CH 3 —CH=CH—CHO
(C) C 6 H 5 —N=N—C 6 H 5 (D) CH 3 —CH=C(Cl)C 2 H 5
3. Among the following, which are tautomers :-

(A) CH2—C—CH3 and CH2=C—CH3 (B) CH 3 —CH 2 —CH=NH and CH 3 —CH=CH—NH 2

O O

O
(C) CH3—N and CH 3 —CH=N—OH (D) glucose and fructose
O
4. Consider the following compounds :

CH3 CH3 CH3

H———OH HO———H HO———H
HO———H HO———H H———OH
CH3 CH3 CH3
(I) (II) (III)

Choose the correct statements :

(A) I and III are enantiomers (B) I and II are diastereomers
(C) II and III are diastereomers (D) I, II and III are all optically active
5. Which will show geometrical isomerism :-

(A) C 6 H 5 –CH=NOH (B)

H H
(C) C 6 H 5 –N=N–C 6 H 5 (D)
H3C CH3
6. Which statement (s) is/are correct for :-

CHO CHO
H———OH HO———H
HO———H H———OH
C6H5 C6H5
(I) (II)
(A) Both are in threo form (B) Both are enantiomers
(C) Both are diastereomers (D) Both are in er ythro form

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 JEE Sprint Chemistry
7. Which of the following compounds are chiral and resolvable :-


(A) C 6 H 5 N(CH 3 ) (C 2 H 5 ) (B) [C 6 H 5 N (CH 3) (C 2 H 5) (C 3H 7 )] Cl –

COOH

(C) CH 3 –CH 2 –CH(CH 3 ) N (CH 3 ) (C 2 H 5 ) (D)

COOH

8. Observe the following structures and pick up the correct option (s) mentioned below :-

CH3 CH3
H Cl H Cl

H H H H

CH2Cl Cl
(A) (B)
(A) The two are position isomers
(B) None of the two shows optical isomerism
(C) Only A shows optical isomerism
(D) The two are not related to each other regarding isomerism

CH3 CH3
H———Cl H———Cl
Cl———H H———Cl
9.
CH2CH3 CH2CH3
(I) (II)
(A) I and II are enantiomers (B) I is 2S, 3S; while II is 2S, 3R
(C) I is 2R, 3R; While II is 2R, 3S (D) I and II are diastereomers
10. Which of the following statements are true regarding following structures :-
COOCH3 COOH COOH
H———OH H———OH H———OH
H———OH H———OH HO———H
COOH COOCH3 COOCH3
(a) (b) (c)
(A) A and B are diastereomers (B) A and C are diastereomers
(C) B and C are diastereomers (D) A and B are enantiomers
11. The R and S enantiomers of an optically active compound differ in :-
(A) their reactivity with chiral reagents
(B) their melting points
(C) their optical rotation of plane polarized light
(D) their solubility in achiral reagents

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 JEE Sprint Chemistry
12. Which of the following statements (s) is (are) incorrect :-

X Y

(A) X is cis- and Y is trans (B) X is Z and Y is E

(C) X is trans and Y is cis (D) X and Y are diastereomers
13. Which of the following compounds will show geometrical isomerism :-
(A) 2-butene (B) propene (C) 1-phenylpropene (D) 2-methyl-2-butene
14. Tautomerism is exhibited by :-

(A) –CH=CH–OH (B) O= =O (C) O (D) O

O O

15. Which of the following notations are correct :

Br F Br Cl
(A) C=C (B) C=C
I Cl I I
(Z) (E)

H3C CH3 H3C CH2CH2CH3

(C) C=C (D) C=C
H H H CH3
(Z) (E)

16. For which of the following pairs of compounds are the correct notation given :-

Ph Ph Ph
N=N and N=N
(A) Ph
Anti-azobenzene Syn-azobenzene

H3C H3C OH
C=N C=N
(B) H OH and H
Syn-acetaldoxime Anti-acetaldoxime

H H
CO2H H
C=C C=C
H CO2H
and
(C)
NH2 NH2
Trans-o-aminocinnamic acid Cis-o-aminocinnamic acid

H3C CH2CH2CH3 ClCH2 CH3

C=C and C=C
(D) H CH3 BrH2C CH3
Z-isomer E-isomer

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 JEE Sprint Chemistry
17. Which of the following statements are correct :-

CH3
(A) CH 3 CH 2 CH 2 CH 2 OH and CH3CHCH2OH represent chain isomerism
(B) CH 3 CH 2 CH 2 CH=CH 2 and CH 3CH 2CH = CHCH 3 are examples of position
isomerism
(C) C 2 H 5 OCH 3 and CH 3 CH 2 CH 2 OH represent functional-group isomerism
(D) CH 3 CH 2 NH 2 and CH 3 NHCH 3 are examples of metamerism
18. Which of the following are optically active :-

(A) H 2 C=C=CH 2 (B)

C=C=C

F F Cl
H
H —CO2H
(C) H N (D)
2 NH2
F F
19. An enantiomerically pure acid is treated with racemic mixture of an alcohol having one chiral carbon. The
ester formed will be :
(A) optically active mixture (B) pure enantiomer
(C) meso compound (D) racemic mixture
20. Tartaric acid molecule contains two asymmetric carbon atoms. The number of optical isomers of tartaric
acid is :-
(A) 2 (B) 3 (C) 4 (D) 5

ANSWER K EY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
An s . A,B,C B,C,D B,C A ,B,C A ,B,C ,D A ,B B,C A ,C B,D B,C ,D A,C A,B A,C A,C ,D A ,C
Qu e. 16 17 18 19 20
An s . B,C ,D A ,B,C ,D B,C A B

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 JEE Sprint Chemistry
Aliphatic Hydrocarbons
SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER)
1. The smallest alkane which can show optical isomerism possesses -
(A) 5 carbons (B) 6 carbons (C) 7 carbons (D) 8 carbons
2. The appropriate reagent for the transformation
O

CH3
is-
HO HO
(A) Zn(Hg)/HCl (B) NH 2NH 2,OH – (C) H2/Ni (D) NaBH 4
3. The relative reactivity of 1ºH, 2ºH and 3ºH in bromination reaction has been found to be
1 : 82 : 1600 respectively. In the reaction -

CH3 CH3 CH3

hv
CH3–CH–CH3 (excess) + Br2 CH3–C–CH3+CH3–CH–CH2–Br
Br
(A) (B)

the percentage yields of the products (A) and (B) are expected to be -
(A) 99.4%, 0.6% (B) 50%, 50% (C) 0.6%, 99.4% (D) 80%,20%
4. The least reactive alkane towards free-radical substitution reactions is-
(A) CH 4 (B) (CH 3 ) 3 CH (C) CH 3 CH 3 (D) CH 3 CH 2 CH 3
5. For the reaction

H2SO4
CH2OH

the major product is :

(A) CH2 (B) CH3 (C) (D)

6. Propene is allowed to react with B2D6 and the product is treated with acetic acid. The final product obtained
is -
(A) 1–deuteriopropane (B) 2–deuteriopropane
(C) 1–deuteriopropene (D) 2–deuteriopropene
7. 1–Methylcyclohexene is allowed to react with B 2H 6 . The product is then treated with H 2 O 2 and NaOH.
The reaction is -

1.B2H6
–
2.H2O2/OH
CH3

The product formed is

(A) 1–methylcyclohexanol (B) 2–methylcyclohexanol
(C) methylcyclohexane (D) cyclohexanol

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 JEE Sprint Chemistry
8. Propene on reaction with ICl produces mainly -
(A) 1–chloro–2–iodopropene (B) 2–chloro–1–iodopropane
(C) (±)–2–chloro–1–iodopropane (D) (±)–1–chloro–2–iodopropane
9. Consider the reaction
CH3
+ – Heat
CH3CH2CH2–N–CH2CH3 OH
CH3
Which of the following is formed in major amount
(A) CH 2 =CH 2 (B) CH 3 CH=CH 2
(C) Both (A) and (B) in equal amount (D) None, as no reaction takes place
10. In the addition of HBr to propene in the absence of a peroxide, the first step involves the addition of -
(A) H + (B) Br – (C) H  (D) Br 
11. In the reaction
1.Hg ( OAc ) ,H O
CH 3CH 2CH=CH 2 2
2.NaBD 4
2

the product obtained is -
(A) CH3CH2CHOHCH2D (B) CH3CH 2CHDCH2OH
(C) CH3CH2CD(OH)CH3 (D) CH3CH 2CD2CH 2OH
12. The major product obtained in the reaction of 1,3-Butadiene with HCl (1 mole) at a higher temperature
(100ºC or above) is
(A) 3,4–dichloro–1–butene (B) 3–chloro–1–butene
(C) 1–chloro–2–butene (D) 2–chloro–2–butene
13. An optically active hydrocarbon (X) on catalytic hydrogenation gives an optically inactive compound (Y),
C 6 H 14 . The hydrocarbon (X) is-
(A) 3–methyl–1–pentene (B) 3–methyl–2–pentene
(C) 2–ethyl–1–butene (D) 3–methylcyclopentene
14. The addition of HCl to 1–phenylpropene gives-
(A) C 6 H 5 CHClCH 2 CH 3 (B) C 6 H 5 CH 2 CHClCH 3
(C) C 6 H 5 CH 2 CH 2 CH 2 Cl (D) C 6 H 5 CH(CH 3 )CH 2 Cl
15. The reduction of 4–octyne with H 2 in the presence of Pd/CaCO 3 – quinoline gives-
(A) trans–4–octene (B) cis–4–octene
(C) a mixture of cis–and trans–4–octene (D) a completely reduced product C 8 H 18
16. The ease of formation of free radicals follows the order -
 
(A) 3 º  2 º  1 º  C H 3 (B) C H 3  1 º  2 º  3 º
 
(C) 1 º  2 º  3 º  C H 3 (D) 2 º  1 º  3 º  C H 3
17. Which of the following has the lowest heat of hydrogenation per mole -
(A) cis–2–Butene (B) trans–2–Butene (C) 1–Butene (D) 1,3–Butadiene
18. The intermediate formed during the addition of HCl to propene in the presence of peroxide is-
   
(A) CH 3 C HCH 2 Cl (B) CH 3 CH 2 C H 2 (C) CH 3 C HCH 3 (D) CH 3 CH 2 C H 2

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 JEE Sprint Chemistry

19. The order of stability of the alkenes

R 2 C=CR 2 , R 2 C=CHR, R 2 C=CH 2 , RCH=CHR, and RCH=CH 2
I II III IV V
is -
(A) I > II > III > IV > V (B) I = II > III > IV > V
(C) II > I > IV > III > V (D) V > IV > III > I > II
20. Which of the following will not react with an ammonical silver nitrate solution :
(A) CH3CCH (B) (CH3)2CH–CH (C) CH3CCCH3 (D) HCCH

ANSWER KEY
Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans . C B A A C B B B A A A C A A B A D C A C

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 JEE Sprint Chemistry
Level–2
SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS)

1. Which of the following reactions will result in the formation of a chiral centre in the product -
(A) CH 3 CH=CHCH 3 +HBr  (B) CH 3 CH=CH 2 +HOBr 

H2O2
(C) CH 3 CH 2 CH=CH 2 +HBr  (D) CH 3 CH 2 CH=CH 2 +HBr 

2. Propene on reaction with N–bromosuccinimide in CCl4 produces -

(A) 1, 2–dibromopropane (B) 3–bromopropene
(C) 1–bromopropene (D) 2–bromopropene
3. cis–2–Butene on reaction with Br2 in CCl4 produces mainly -
(A) 1–bromo–2–butene (B) 2,3–dibromobutane
(C) meso–2,3–dibromobutane (D) (±) 2,3–dibromobutane
4. The bond dissociation energies of the following

CH3–H CH3CH2–H CH2=CH–CH2–H C6H5–H

I II III IV

vary in the order :

(A) I > II > III > IV (B) IV > III > II > I (C) IV > I > II > III (D) II > I > IV > III
5. Which of the following decolourises alkaline KMnO 4 solution
(A) C3H 8 (B) C 2H 4 (C) CH 4 (D) CCl 4
6. Compounds capable of reacting with ammonical AgNO 3 solution are

(A) CH3 CH C CH (B) HC CH (C) 1- Butyne (D) all the above

CH3

7. A hydrocarbon which decolourises KMnO 4 but does not give any precipitate with ammoniated AgNO 3
(A) Benzene (B) Acetylene (C) Butyne (D) 2–Butene
8. Compound 'A' on chlorination gives compound 'B', compound 'B' reacts with alc. KOH gives gas 'C', which
decolourise Baeyer reagent. ozonolysis of compound 'C' gives only HCHO compound. 'A' is :
(A) C 2 H 6 (B) C 2 H 4 (C) C 4 H 10 (D) C 2 H 5 Cl

9. Which reagent converts propene to 1–propanol

(A) H 2 O, H 2 SO 4 (B) B 2 H 6, H 2 O 2 , OH –
(C) Hg(OAc) 2 ,NaBH 4 /H 2 O (D) Aq. KOH
10. Which one of the following alkenes will react faster with H 2 under catalytic hydrogenation conditions :
[R = Alkyl Substituent]

R R R R R R R H
(A) (B) (C) (D)
R R H H R H R H

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 JEE Sprint Chemistry

11. Arrange the following in order of increase/decrease in boiling point.

CH3CH2CH2CH2CH3 (CH3)2CHCH2CH3 (CH3)4C

I II III

(A) I > II > III (B) II > I > III (C) III > I > II (D) III < II < I
12. What are the products obtained upon the ozonolysis of 2-pentene ?
(A) CH3CH2CHO (B) CH3CHO (C) CH3COCH3 (D)CH3COCH2CH 3
13. Which of the following can be used for the preparation of propane ?

2 61.B H 1.Mg / ether

(A) CH 3CH=CH 2 
2.CH 3 COOH
 (B) CH3CH2CH2Cl 
2.H 2 O



Re d P / HI / 150  C NaOH / CaO

(C) CH3CH2CH2I  
 (D) CH3CH 2CH 2COONa 



14. Which of the following are correct :

1.O 3
(A) 
2. Zn,H O
 OHC–CH2CH2CH2–CHO
2
H H

O
(B) C6H5C–OOH
CH2Cl2
H H
H H
O

KMnO 4 H H
(C) 
cold dilute solution


H H OH OH

O O
KMnO 4
(D)   O—CCH CH CH C—O–
–
OH – ,heat 2 2 2
H H

15. 2-Bromo-3-phenylpropane can be synthesised by

(A) C6H 5CH 2CH(OH)CH3+PBr3 
(B) C 6 H 5CH=CHCH 3+HBr+ benzoyl peroxide 
(C) C 6H 5 CH 2 CH 2 CH 3 +Br 2+ light 
(D) none of these
16. The nitration of propane with concentrated HNO 3 gives :

(A) CH3CH2CH2NO 2 (B) CH3CHCH3 (C) CH3CH2NO 2 (D) CH 3NO 2

NO2

17. Which of the follwing will react with sodium metal :

(A) Ethyne (B) 1-Butyne (C) 2-Butyne (D) Ethane

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 JEE Sprint Chemistry

A
18. —CH=CH2 —CH2CH2OH

B
—CHCH3

OH
C —CH2CH3
OH

A, B and C are :
(A) simple hydration
(B) hydroboronation, mercuration-demercuration, hydration
(C) hydration, hydroboronation, mercuration-demercuration
(D) mercuration-demercuration, hydration, hydroboronation

O O
ozonolysis
C 9 H 14 
19. 
(A )

Hence A is :

(A) (B) (C) (D)

Y X
20.
HO OH HO OH

Select X and Y out of :

I : MnO 4 /OH– II : HCO3H

(A) X -I, Y- II (B) X -II, Y- I (C) X -I, Y- I (D) X -II, Y- II

ANSWER KEY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
An s . A , B,D B D C B D D A B B A, D A, B A ,BC,D A ,BC,D A ,B
Qu e. 16 17 18 19 20
An s . A ,BC,D A, B B B A

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 JEE Sprint Chemistry
Aromatic Hydrocarbons
SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER)
1. The correct order of reactivity towards the electrophilic substitution of the compounds aniline (I), benzene (II)
and nitrobenzene (III) is :-
(A) III > II > I (B) II > III > I (C) I < II > III (D) I > II > III
2. Which of the following order is correct for the decreasing reactivity to ring monobromination of the following
compounds :-

CH3 COOH NO2

I II III IV
(A) I > II > III > IV (B) II > III > IV > I (C) I > III > II > IV (D) III > I > II > IV

3. Electrophile N O 2 attacks the following :

CCl3 NO2 CHO O
(A) (II) (III) (IV)


in which cases N O will attack at meta position
2

(A) II and IV (B) I, II and III (C) II and IV (D) I only

4. The strongest deactivating effect on aromatic ring is
(A) –CH 2 Cl (B) –OCH 3 (C) –CH 3 (D) –CCl 3
5. Which of the following is maximum reactive for nitration is :-

(A) (B) (C) (D)

6. The order of decreasing rectivity towards electrophilic reagent for the following :
(a) Benzene (b) Toluene
(c) Chloro benzene (d) Anisole
(A) b > d > a > c (B) d > c > b > a (C) d > b > a > c (D) a > b > c > d
7. Increasing order of the following for electrophilic substitution reaction as –

–CH 3 –COOH

(I) (II) ( I II )
(A) I < II < III (B) III < II < I (C) II < III < I (D) I < III < II
8. Among the compounds :

CH3 OCH3 CF3

(I) (II) (III) (IV)

the order of decreasing reactivity towards electrophilic substition is :
(A) II > I > III > IV (B) III > I > II > IV (C) IV > I > II > III (D) I > II > III > IV

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 JEE Sprint Chemistry

9. Choose the most reactive among the following compound :

(A) (B) (C) (D)

10. The number of possible dichloronitrobenzene isomers is :

(A) 3 (B) 4 (C) 6 (D) 8
11. The major product formed on monobromination of phenylbenzoate is :

Br
(A) (B)
O O Br
O O

Br

(C) O (D)
O
O
O
Br
12. The major product formed in the reaction is :

+
—OCH3 + E
(electrophile)

(A) —OCH3 (B) E— —OCH3

—OCH3 —OCH3
(C) (D)
E E

13. The electrophilic aromatic substitution of a compound C6H5Y produces mainly a meta-disubstituted product.
Among the following which one could be the substituent Y ?
(A) —NH 2 (B) —COOH (C) —CH 3 (D) —OCH 3
14. Which of the following is an o-, p-directing but deactivating substituent in an electrophilic aromatic
substitution :
(A) —CCl 3 (B) —Cl (C) —NHCOCH 3 (D) —OCH 3
15. The major product formed in the reaction is :

OMe
AlCl 3
+ (CH3)2 CHCH2Br  


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 JEE Sprint Chemistry

OMe OMe

(A) (B)
CH2 CH(CH3)2 (CH3)2CHCH2

OMe OMe
(C) (D)
C(CH3)3 (CH3)3C

16. The dipole moment of chlorobenzene is 1.6 D. The expected dipole moment of meta-dichlorobenzene is:
(A) 1.6 D (B) 3.2 D (C) 1.6 2 D (D) 0.0 D
17. In the nitration of benzene with a mixture of concentrated HNO3 and concentrated H2SO4, the active species
involved is :

(A) NO 3– (B) NO 2 (C) NO 2– (D) NO 2

18. Which of the following substituted benzene derivatives would produce three isomeric products when one
more substituent is introduced ?

Cl Cl Cl Cl Cl

Cl Cl
(I) (II) (III) (IV)

(A) I, II and III (B) I and III (C) II and IV (D) I and IV
19. In the sulphonation of benzene, the active electrophilic speices is :
(A) SO 2 (B) SO 3 (C) SO 24  (D) HSO 4
20. The Friedel-Crafts reaction of benzene with n-butyl chloride at 0°C produces :

CH3
(A) C 6 H 5 —CH 2 CH 2 CH 2 CH 3 (B) C6H5CH—CH2CH3

(C) C6H5—CH2—CH—CH3 (D) all of these

CH3

21. Sulfonation differs from most of electrophilic aromatic substitution reactions with the fact that the reaction-
(A) is reversible (B) requires Lewis acid as catalyst
(C) is explosive (D) takes place at high temperature
22. Cumene on treatment with KMnO 4 gives -

H3C COOH COOH CHO COOH

(A) (B) (C) (D)

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 JEE Sprint Chemistry

23. Benzene reacts with CH 3COCl in the presece of anhyd. AlCl 3 to give :
(A) C6H5CH3 (B) C6H5Cl (C) C6H5O2Cl (D) C6H5COCH3

CH3

Br2
24. 
FeBr2
 A (Major product),

then the major product A is -

CH3 CH3 CH3 CH3 CH3

Br
Br
(A) (B) (C) (D) +

Br
Br Br CH3
50% 50%

25. Arrange the following in correct activating order towards EAS -

O
+
—NHCOCH3 —O—C—CH3 —NR3 —NH2
I II III IV

(A) III < I < II < IV (B) IV < I < II < III
(C) III < II < I < IV (D) II < III < I < IV

ANSWER KEY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans . D C B D B C B B B C D C B B D
Qu e. 16 17 18 19 20 21 22 23 24 25
Ans . A D B B A A B D A C

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 JEE Sprint Chemistry
Level–2
SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS)
1. Which of the following groups are m-directing :
(A) —CHO (B) —OH (C) —OCOCH 3 (D) —COOH
2. Amongst the ions the aromatic species are :

H H
H H
(A)  (B) (C) (D)


3. The following three isomeric tribromobenzenes are subjected to mononitriation, which is/are given two
isomers :
Br Br Br
Br

Br Br Br Br
Br
(I) (II) (III)
Which of these would produce three possible mononitrotribromobenzenes :
(A) II and III (B) I and II (C) II (D) III
4. In the reaction the major product formed is :
O

Br2 (1mole )
N—  Fe


O
O
Br N—
(A) N— (B)

Br
O
O

N—
(C) (D) N— Br

Br
5. The major product formed in the reaction is :

conc.H 2 SO 4
+ HNO3  

NO2
NO2

(A) (B) (C) (D)

NO2
NO2

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 JEE Sprint Chemistry

6. Nitrobenzene reacts with Br2 in the presence of FeBr3 to give m-bromonitrobenzene as the major product.
Which of the following provides the best reason for the formation of m-bromonitrobenzene as the major
product :
(A) The electron density at the meta position is greater than those at the ortho and para positions
(B) Aromaticity is lost in the -complexes formed by the attack of Br + at the ortho and para positioins
but not at the meta position.
(C) The -complex formed by the attack of Br+ at the meta position is the least destabilized and the most
stable among the three -complexes
(D) In the final step of regeneration of benzene ring by the loss of H + from the -complexes, the meta-
oriented -complex loses H + most readily
7. Isopropylbenzene can be prepared by :

H 2 SO 4 H 2 SO 4
(A) Benzene + CH 3 CH = CH 2   (B) Benzene + CH3—CH—CH3  
Cl

AlCl 3 AlCl 3
(C) Benzene + CH3CH—CH3   (D) Benzene + CH 3 CH 2 CH 2 Cl 


Cl
8. Which of the following characteristic does an aromatic compound exhibit :
(A) It should have (4n +2) -electrons in the ring (B) It should be planar and conjugated
(C) It should have 4n -electrons in the ring (D) It should possess high resonance energy
9. Which of the following groups are meta-directing :
(A) —NH 2 (B) —OH (C) —NO 2 (D) —CN
10. Which of the following groups are ortho-and para-directing :
(A) —OH (B) —CHO (C) —CN (D) —NHCOCH 3
11. Which of the following statements are correct :
(A) An activating group is an electron-releasing group
(B) An activating group activates all positions of the benzene ring
(C) The effect of any group–whether activating or deactivating–is the strongest at the ortho-and para-positions
in the benzene ring
(D) An activating group activates only the ortho-and para-positions in the benzene ring
12. The major products formed in the reaction of toluene with chlorine in the presence of ferric chloride are:
(A) o-chlorotoluene (B) m-chlorotoluene (C) p-chlorotoluene (D) benzyl chloride
13. Benzene can undergo :
(A) substitution (B) addition
(C) elimination (D) oxidation
14. Which of the following statements about the nitration of aromatic compounds are correct :
(A) The rate of nitration of toluene is greater than that of benzene
(B) The rate of nitration of benzene is almost the same as that of hexadeutrobenzene
(C) The rate of nitration of benzene is greater than that of hexadeutrobenzene
(D) Nitration is an electrophilic substitution reaction

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 JEE Sprint Chemistry

15. Halogenation of benzene in presence of AlCl 3 (anhy.) is :

(A) nucleophilic substitution (B) nucleophilic addition
(C) electrophilic substitution (D) free radical substitution
16. Which of the following structures correspond to the product expected, when excess of C 6H 6 reacts with
CH 2 Cl 2 in presence of anhydrous AlCl 3 ?

C1
(A) —CH— (B) —CHCl2

Cl

(C) —C— (D) —CH2—

Cl

17. Select the incorrect statement among the following :

(A) benzene undergoes predominantly electrophilic substition reactions
(B) toluene is more easily sulphonated than benzene
(C) benzene reacts with CCl 4 in the presence of anhydrous AlCl 3 to give triphenyl methyl chloride
(D) benzene reacts with chlorine (Cl 2) in presence of light to give benzyl chloride
18. Identify the correct order of reactivity in electrophilic substitution reactions of the following compounds:

C2H5 Cl NO2
Cl NO2

(I) (II) (III) (IV)

(A) I > II > III > IV (B) IV > III > II > I
(C) II > I > III > IV (D) II > III > I > IV
19. The structure of Wheland intermediate obtained after the attack of Br + on anilinium ion is :

H Br + +
NH3 NH3
H
(A) + (B) + Br

H Br + +
NH3 NH3
H
(C) + (D) + Br

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 JEE Sprint Chemistry

O O
20. Conjugation of electron withdrawing groups, e.g., —CHO, —C—R, —C—OR,—CN, —NO 2 activates

nucleophilic attack in halobenzene. The order of reactivity of these groups is :

O O O
(A) —NO 2 >—C  N > —C—H > —C—R> —C—OR

O O O
(B) —C—H> —C—R> —C—OR > —C  N >—NO 2

O O O
(C) —C  N >—NO 2 > —C—H> —C—R> —C—OR

O O O
(D) —C—H>—NO 2 >—C  N > —C—OR> —C—R

ANSWER KEY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
An s . A B,C D D B C A ,C ,D A ,B,D C ,D A ,D A ,B,C A A ,B,D A ,B,D C
Qu e. 16 17 18 19 20
An s . D C ,D C B A

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 JEE Sprint Chemistry
Alkyl and Aryl Halides
SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER)

H OH
1. The product formed in the reaction + SOCl2  is-

Cl H H SO3H
H O Cl
(A) (B) (C) (D)
Cl H

2. The reaction + SOCl2 N

Cl + SO2 + N+ Cl –
HO H H H

proceeds by the mechanism

(A) S N1 (B) S N 2 (C) SNi (D) S E 2

3. 1, 3- Dibromopropane reacts with metallic zinc to form

(A) propene (B) cyclopropane (C) propane (D) hexane
4. Consider the following reaction sequence,

aq.H 2 SO 4 PCl 5
CH3C  CH  
 A   B.
HgSO 4 Heat

The products (A) and (B) are, respectively,

(A) CH 3COCH 3 and CH 3CCl 2CH 3 (B) CH 3CH 2 CHO and CH 3CH 2CHCl 2
(C) CH 3CHOHCH 3 and CH 3CHClCH 3 (D) CH 3CH 2 CH 2OH and CH 3 CH 2CH 2Cl
5. Which of the following has highest dipole moment:
(A) CH 3Cl (B) CH 3F (C) CH 3Br (D) CH 3I

6. In S N1 the first step involves the formation of

(A) free radical (B) carbanion (C) cabocation (D) final product
7. To form alkane isonitrile, alkyl halide is reacted with:
(A) KCN (B) AgCN (C) HCN (D) NH 4CN
8. Which one of the following compounds most readily undergoes substitution by S N 2 mechanism ?

CH3 Cl H3C CH3

(A) H3C (B) H3C (C) H3C (D)

Cl
C3H7 H3C
Cl
Cl

9. Sec. Butyl chloride undergo alkaline hydrolysis in the polar solvent by

(A) S N 2 (B) S N1 (C) S N1 and S N 2 (D) none of these

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 JEE Sprint Chemistry
10. Grignard reagent can be prepared by

dry dry
(A) CH 3 —CH 2—Cl + Mg 
ether
(B) CH3 CH CH2 + Mg 
ether

Cl OH

CH3
dry
(C) CH3 C OH + Mg 
ether
(D) All of them
CH3

11. Most stable carbocation formed from (CH 3) 3C–Br, (C 6H5) 3CBr,(C 6H 5) 2CHBr and C 6H5CH 2Br would be

   
(A) C 6H 5 C H 2 (B) (CH3)3 C (C) (C 6H 5) 3 C (D) (C 6H 5) 2 CH

12. For the reaction

alc. KOH
CH3 CH CH CH3
CH 3 CH(X)CH 2CH 3
CH2 CH CH2 CH3

(A) CH 3—CH CH—CH 3 predominates (B) CH 2 CH—CH 2 —CH 3 predominates

(C) Both are formed in equal amounts (D) The product ratio depends on the halogen
13. The products of reaction of alcoholic silver nitrite with ethyl bromide are
(A) Ethane (B) Ethene (C) Ethyl alcohol (D) Nitro ethane
14. The reaction ,CH3Br + OH–  CH3OH + Br– obeys the mechanism
(A) S N1 (B) S N 2 (C) E1 (D) E2
15. Ethylidene chloride can be prepared by the reaction of HCl and
(A) Ethane (B) Ethylene (C) Acetylene (D) Ethylene glycol
16. 1–phenyl–2–chloropropane on treating with alc. KOH gives mainly
(A) 1–phenylpropene (B) 2–phenylpropene
(C) 1–phenylpropane–2–ol (D) 1–phenylpropan–1–ol
17. Grignard reagent is obtained when magnesium is treated with
(A) Alkyl halide in presence of alcohol (B) Alkyl halide in presence of phenol
(C) Alkyl halide in presence of dry ether (D) Alkyl halide in presence of alcoholated ether
18. Ethylene reacts with bromine to form -
(A) Chloroethane (B) Ethylene dibromide (C) Cyclohexane (D) 1-bromo propane
Br2 KCN
19. C2H4   X  Y ; Y is
(A) CH 3CH 2CN (B) NC—CH 2 —CH 2 —CN
(C) Br—CH 2 —CH 2 CN (D) Br—CH CHCN
20. Reactivity order of halides for dehydrohalogenation is
(A) R – F > R – Cl > R – Br > R – I (B) R – I > R – Br > R – Cl > R – F
(C) R – I > R – Cl > R – Br > R – F (D) R – F > R – I > R – Br > R – Cl
21. Which of the following is least reactive in a nucleophilic substitution reaction
(A) CH 2 CHCl (B) CH 3 CH 2 Cl (C) CH 2 CHCH 2 Cl (D) (CH 3) 3 C–Cl

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 JEE Sprint Chemistry
22. The correct reactivity order of alcohols towards H–X will be

OH
(I) CH 2 CH—OH (II) H3C (III) CH 3—CH 2 —OH (IV) CH3 CH CH3
CH2
OH
(A) II > I > III > IV (B) IV > III > II > I (C) II > IV > I > III (D) II > IV > III > I
Al O
aq.NaOH 2 3
23. Identify 'Z' in the following reaction series, CH3.CH2CH2Br   (X) 
Heat

 (Y) 
HOCl
 (Z) :

(A) Mixture of CH3CH CH2 and CH3CH CH2 (B) CH3 CH CH2
Cl Cl OH OH OH Cl

(C) CH3 CH CH2 (D) CH3 CH CH2

Cl OH Cl Cl
24. For the reaction,
ZnX 2
C2H5OH + HX   C2H5X,
 the order of reactivity is

(A) HI > HCl > HBr (B) HI > HBr > HCl (C) HCl > HBr > HI (D) HBr > HI > HCl
25. Ethyl alcohol reacts at a faster rate with HI than with HCl in forming the corresponding ethyl halides under
identical conditions mainly because -
(A) HI, being a stronger acid, protonates ethyl alcohol at oxygen much better and helps substitution
(B) the bond length in HI is much shorter than that in HCl
(C) I– is a much better leaving group
(D) I– is a much better nucleophile than Cl–

ANSWER KEY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans . B B B A A C B B C A C D D B C
Qu e. 16 17 18 19 20 21 22 23 24 25
Ans . A C B B B A D B B D

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 JEE Sprint Chemistry
Level-2
SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS)
1. Which of the following does/do produce a white precipitate of AgCl on warming with alcoholic silver
nitrate?
(A) Allyl chloride (B) t-Butyl chloride (C) Benzyl chloride (D) Vinyl chloride
2. What is the order of reactivity of the following compounds towards nucleophilic substitution?

Cl Cl Cl Cl

(I) (II) (III) (IV)

(A) I < II < III < IV (B) IV < III < II < I (C) IV < I < II < III (D) IV < II < I < III
3. The order of decreasing nucleophilicity of the following is
(A) H 2O > OH – > CH 3COO – > CH 3O – (B) CH 3O– > OH – > CH 3COO – > H 2O
(C) CH3COO– > CH3O–> OH– > H2O (D) HO – > CH 3O –> CH 3COO –> H 2 O
4. The order of decreasing SN1 reactivities of the halides
CH 3 CH 2 CH 2 Cl CH 2 = CHCHClCH 3 CH 3 CH 2 CHClCH 3
I II III
(A) I > II > III (B) II > I > III (C) II > III > I (D) III > II > I
5. Consider the following anions.

O O O
O–
CF3–S–O– C6H5–S–O– CH3–C–O–
O O
(II) (III) (IV)
(I)

When attached to sp3- hybridized carbon, their leaving group ability in nucleophilic substitution reactions
decreases in the order
(A) I > II > III > IV (B) I > II > IV > III (C) IV > I > II > III (D) IV > III > II > I
– – –
6. The basicity of RO ,HO , RCOO , ROH, and H2O are of the order -
(A) HO– > RO– > H2O > ROH > RCOO–
(B) RO– > HO– > RCOO– > ROH > H2O
(C) H2O > ROH > RCOO– > HO– > RO–
(D) ROH > H2O > HO– > RCOO– > RO–
7. Which of the following are aprotic solvents :
(A) DMSO (B) DMF (C) H 2 O (D) CH 3 COOH
8. Which is/are true statements (s) :
(A) Protonation increases electrophilic nature of carbonyl group
(B) CF3 SO 3– is better leaving group than CH 3 SO 3–
(C) Benzyl carbonium ion is stabilised by resonance

OH
(D) CCl 3 CH is stable,due to H-Bonding
OH

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 JEE Sprint Chemistry

Me
SOCl2
9. Ph C—OH 
inC 5 H 5 N


Which statement is true for the above reaction ?

(A) Retention of configuration (B) Inversion of configuration
(C) Inversion and Retention both (D) None
10. Which of the following undergoes hydrolysis most easily

Cl Cl
(A) (C)
NO2
NO2
Cl Cl
(C) (D)
NO2 NO2 NO2 NO2
11. A compound 'A' formula of C3H6Cl2 on reaction with alkali can give 'B' of formula C3H6O or 'C' of formula
C3H4. 'B' on oxidation gave a compound of the formula C3H6O2. 'C' with dilute H2SO4 containing Hg2+ ion
gave 'D' of formula C3H6O, which with bromine and alkali gave the sodium salt of C2H4O2. Then 'A' is
(A) CH 3 CH 2CHCl 2 (B) CH 3CCl 2CH 3 (C) CH 2ClCH 2CH 2Cl (D) CH 3 CHClCH 2Cl
12. Isobutyl magnesium bromide with dry ether and absolute alcohol gives

(A) CH3 CH CH2OH and CH 3CH 2MgBr (B) CH3 CH CH2 CH2 CH3 and Mg (OH) Br
CH3 CH3

(C) CH3 CH CH3 , CH2 CH2 and Mg(OH)Br (D) CH3 CH CH3 and CH 3CH 2OMgBr
CH3 CH3

13. Following reaction is

H H
CH3(CH2)5  (CH2)5CH3
OH
C Br  HO C
H3C CH3

(A) E1 (B) S N1 (C) E2 (D) S N 2

14. On treatment with chlorine in presence of sunlight, toluene gives the product -
(A) o-chloro toluene (B) 2, 5-dichloro toluene
(C) p-chloro toluene (D) Benzyl chloride

15. In S N1 reaction an optically active substrates mainly gives :

(A) Retention in configuration (B) Inversion in configuration

(C) Racemic product (D) No product
16. Alkyl iodides can be prepared by :-

CCl 4 acetone
(A) RCH 2 COOAg + I 2 

RCH 2 I (B) RCH 2 Cl +NaI 
 RCH 2 I + NaCl

(C) R—OH + HI  RI + H 2 O (D) CH 4 + I 2  CH 3 I

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 JEE Sprint Chemistry

17. Which of the following reagents can be used to prepare an alkyl halide :-
(A) NaCl (B) HCl + ZnCl 2 (C) SOCl 2 (D) PCl 5
18. Which of the following reactions depict the nucleophilic substitution of C 2H 5Br :-

(A) C 2 H 5 Br + C 2 H 5 SNa  C 2 H 5 SC 2 H 5 + NaBr

Na  C 2 H 5 OH
(B) C 2 H 5 Br   C 2 H 6 +HBr

(C) C 2 H 5 Br + AgCN  C 2 H 5 NC + AgBr

(D) C 2 H 5 Br + KOH  C 2 H 5 OH+ KBr

19. For an S N 2 reaction, which of the following statements are true :-

(A) The rate of reaction is independent of the concentration of the nucleophile

(B) The nucleophile attacks the C-atom on the side of the molecule opposite to the group being displaced
(C) The reaction proceeds with simultaneous bond formation and rupture
(D) None of these

20. Which of the following is an S N 2 reaction :-

(A) CH 3 CH 2 Br + KOH  CH 3 CH 2 OH + KBr

(B) CH 3 CH 2 Br + CH 3 CH 2 ONa  CH 3 CH 2 OCH 2 CH 3 + NaBr
(C) (CH 3 ) 3 CBr + KOH  (CH 3 ) 3 COH+ KBr

CH3 CH3

(D) CH3—CH2—C—Br + KOH CH3CH2—C—OH + KBr

CH3 CH3

ANSWER KEY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans . A ,B ,C C B C B B A ,B A ,B ,C ,D B D A D D D C
Qu e. 16 17 18 19 20
Ans . B .C B ,C ,D A ,C ,D B ,C A ,B

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 JEE Sprint Chemistry
Alcohol, Phenol, Ether
SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER)
1. Consider the following reaction sequence
dil.KMnO 4 PCl 5
CH 2 = CH 2 cold
 A 
excess
B

The products (A) and (B) are, respectively :

(A) CH 3 CH 2 OH and CH 3 CH 2 Cl (B) CH 3 CHO and CH 3 CHCl 2
(C) CH 2 OH CH 2 OH and CH 2 ClCH 2 Cl (D) CH 2 OHCH 2 OH and CH 2 OHCH 2 Cl
2. Consider the following reaction sequence,
HCl aq.KOH
CH 3 C  CH 
2 m ole
 A 
Heat
B

The products (A) and (B) are, respectively,

(A) CH 3 CH 2 CHCl 2 and CH 3 CH 2 CHO (B) CH 3 CCl 2 CH 3 and CH 3 COCH 3
(C) CH 3 CCl 2 CH 3 and CH 3 C  CH (D) CH 3 CHClCH 2 Cl and CH 3 CHOHCH 2 OH
3. Consider the following chlorides :

CH2Cl CH3 CH2Cl

;
(A) (B)

CH3O CH2Cl O2N CH2Cl

;
(C) (D)
The order of reactivity of A, B, C and D towards hydrolysis by S N1 mechanism is :
(A) A < B < C < D (B) D < C < B < A (C) D < A < B < C (D) C < B < A < D
4. In the following reaction sequence
aq.H 2 SO 4 1.CH 3 MgI
Ph – C  CH 
Hg 2 

 A 
2.H 2 O
B

the product (B) is :

Ph CH3

C
(A) PhCOCH 3 (B) PhCH 2 CHOHCH 3 (C) (D) PhCH 2 COCH 3
CH3 OH
5. Consider the following reaction.

O16
16  H
CH3 – C –O18 –C2H5 + HO
2

Heat

The products formed in the reaction are

O16 O16

(A) CH3 – C –O16 H and C 2 H 5 O 18 H (B) CH3 – C –O18 H and C 2 H 5 O 16 H

O16 O
18

(C) CH3 – C –O16 H and C 2 H 5 O 16 H (D) CH3 – C –O18 H and C 2 H 5 O 18 H

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 JEE Sprint Chemistry

6. Consider the following reaction sequence,

O
1.CH 3 MgI POCl 3
 A  B
2.H 2 O Pyridine,0  C

The product (B) is-

CH3 CH3 CH2 CH3

(A) Cl (B) OPOCl2 (C) (D)

7. Propene is allowed to react with m-chloroperoxobenzoic acid. The product (A) is then reduced with LiAlH4
in dry ether to give (B).
MCPBA 1. LiAlH 4
CH 3 CH  CH 2   A  
B
2. H 3 O

The structure of the product (B) is:

(A) CH 3 CHOHCH 2 OH (B) CH 3 CH 2 CH 2 OH (C) CH 3 CHOHCH 3 (D) CH3–CH–CH2

O
8. 2-Phenylethanol may be prepared by the reaction of phenylmagnesium bromide with :

(A) HCHO (B) CH 3 CHO (C) CH 3 COCH 3 (D)

O

9. In the reaction

Cl CH 2 Br + CH 3 CHO + Mg 
dry ether H 3O 
 A  B

the product (B) is :

(A) CH3CH CH2Br (B) Cl CH2CHCH3

OH OH

(C) CH3–CH CH2CHCH3 (D) CH2=CH CH2Br

OH OH

10. The final product in the reaction is :

KOH
Ph—OH + CCl 4  product

(A) Salicyl aldehyde (B) Salicylic acid (C) Methyl salicylate (D) Benzyl chloride

11. In the reaction of phenol with CHCl3 and aqueous NaOH at 70°C, the eletrophile attacking the ring is :

(A) CHCl 3 (B) C HCl 2 
(C) CCl (D) COCl 2
2

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 JEE Sprint Chemistry

OH
12. CHCl 3  KOH
  Product :

about above reaction the incorrect statement is

(A) The name of reaction is Riemer teimann's reaction
(B) The intermediate in the reaction is dichloro carbene
(C) The final product is o-hydroxy benzaldehyde (D) the final product is benzyl chloride

13. The final product (IV) in the sequence of reactions is :

CH2 CH2
CH 3 CHOH Mg
| PBr2 O H2O
I II III IV
CH 3 Ether

(A) CH3 CHOCHCH

2 2OH (B) CH3 CHCH2CH2Br

CH3 CH3

(C) CH3 CH CH2CH2OH (D) CH3 CHOCHCH

2 3

CH3 CH3

14. The reaction of 1 mol each of p-hydroxyacetophenone and methyl magnesium iodide will give :

(A) CH4 + IMgO COCH3 (B) CH3O COCH3

OMgI MgI

(C) H3C C OH (D) CH3O COCH3

CH3

15. The product obtained in the reaction RCH CH2C  ? is :

OH

OH

CH2 C O
(A) RCH CH2 (B) R CH HC R
O C CH2
O C= O
O

(C) RCH = CHCOOH (D) None of these

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 JEE Sprint Chemistry

16. The final product obtained in the reaction is :

H3C OCH3 + HBr

(A) CH3 OH (B) CH3 Br

(C) CH3 O CH3 (D) None of these

17. The acidity of the compounds RCOOH, H2CO3, C6H5OH, ROH decreases in the order :
(A) RCOOH > H 2CO 3 > C 6H 5 OH > ROH (B) C 6H 5 OH > RCOOH > H 2CO 3 > ROH
(C) ROH > C 6H 5 OH > RCOOH > H 2CO 3 (D) H 2CO 3 > RCOOH > C 6H 5 OH > ROH
18. Arrange the following in order of decreasing acidic strength. p- nitrophenol (I), p-cresol (II), m-cresol (III),
phenol (IV) :
(A) I > II > III > IV (B) IV > III > II > I (C) I > III > II > IV (D) III > II > I > IV
19. For the cleavage of ethers by halogen acids, the order of reactivity of halogen acids is :
(A) HI > HBr > HCl (B) HBr > HI > HCl
(C) HCl > HBr > HI (D) Ethers do not undergo cleavage
20. Consider the following reactions :

dil.KMnO4 (CH3COO)4Pb
A B
Cold

The product (B) is

OH CH3COO O O

(A) (B) (C) (D)

O O
OH CH3COO

21. The major product (A) formed in the reaction

H2SO4 A

HO OH

is :

(A) (B) (C) (D)

O O O

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 JEE Sprint Chemistry
22. In the reaction

+
Dry ether H3O
Cl CH3Br + CH3CHO + Mg A B

the product (B) is :

(A) CH3CH CH2Br (B) Cl CH2CHCH3

OH OH

(C) CH3–CH CH2CHCH3 (D) CH2=CH CH2Br

OH OH

23. The products formed in the reaction are :

O
18 H2SO4
C6H5 C OH + CH3OH
Heat

O O
18 18
(A) C6H5 C OCH3 and H2O (B) C6H5 C OCH3 and H2O

O
18 18
(C) C6H5 C CH2OH and H2O (D) C6H5OCH3, CO and H2O

24. The conversion

O OH

CH3 C CH2CH2COCH
2 3
CH3 CH CH2CH2COCH
2 3

(A) LiAlH4 and then H+ (B) NaBH4 and then H+

(C) H2/ Carbon (D) None of these
25. Identify the final product of the reaction :
+
H3O
CH3MgBr + CH2CH2 ?

(A) CH 3 OH (B) CH 3 CH 2 OH (C) (D) CH 3 CH 2 CH 2 OH

ANSWER KEY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
An s . C B C C A C C D B B C D C A C A A A A C
Qu e. 21 22 23 24 25
An s . A B A B D

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 JEE Sprint Chemistry
Level–2
SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS)
1. Consider the following reaction.

Br
H2O
+ KOH 
SN 2

H
H
CH3

(1R, 3S)-cis-1 -Bromo -3-methylcyclohexane

The product formed in the reaction is
(A) (1R, 3S)-cis-3- methylcyclohexanol (B) (1S,3R)-cis-3-methylcyclohexanol
(C) (1S, 3S)-trans-3-methylcyclohexanol (D) (1R,3R)-trans-3-methylcyclohexanol
2. Consider the following alcohols

CH2OH CH2OH CH2OH CH2OH

O2N CH3O Br
(I) (II) (III) (IV)

The order of decreasing reactivities of these alcohols towards nucleophilic substitution with HBr is
(A) III > I > IV > II (B) III > I > II > IV (C) I > III > IV > II (D) I > III > II > IV
3. The product formed in the following reaction

O COOC2H5
NaBH 4
  is
H 2 O,CH 3 OH

O CH2OH HO CH2OH HO COOC2H5 COOC2H5

(A) (B) (C) (D)

4. Consider the following sequence of reactions.

CH 3 MgBr 1.HCHO
C2H5C  CH  A  
B
2.H 3 O

The product (B) is

(A) CH 3 CH 2OH (B) C 2 H 5 C  CHCH 2 OH

|
CH 3

(C) C 2 H 5 C  C – CH – CH 3 (D) C2H5C  C – CH2OH

|
OH
5. In the transformations
ArCO 3 H 1.LiAlH 4 ,Et 2 O
PhCH = CH2 
CH 2 Cl 2
 A 
2.H 2 O

B

the end product (B) is

(A) PhCH—CH2 (B) PhCHOH CH 3 (C) PhCH 2 CH 2COAr (D) PhCH 2 CH 2OH
O

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 JEE Sprint Chemistry

6. The reactivities of methanol (1), 1- propanol (II), 2- butanol (III) and 2- methyl-2- propanol (IV) towards
sodium metal follow the order
(A) I > II > III > IV (B) IV > III > II > I (C) I > IV > II > III (D) IV > II > III > I
7. In the reaction
heat
(CH 3) 3 C–O–CH 2CH 3 + HI  
(1 mole )

the product(s) formed is (are)

(A) (CH 3) 3 C–OH and CH 3CH 2I (B) (CH 3) 3C–I and CH 3CH 2OH


(C) (CH 3) 3C–I and CH 3CH 2I (D) (CH 3 ) 3 C  O  CH 2 CH 3 I 
|
H

8. Consider the following sequence of reactions.

1. KH 1. B 2 H 6
OH   A   B
2. PhCH 2 Br 
2. H 2 O 2 / OH

The end product (B) is

(A) O Ph (B) HO O Ph

OH
Ph OH
(C) O Ph (D)

9. In the reaction

CH3
+ HCl 
H O

the major product formed is

Cl OH
(A) OH (B) Cl

Cl
(B) (D) Cl
Cl

10. Consider the following reaction.

14
CH2–CH–CH2Cl
CH 3 O  A
O
The product (A) is
14 14
(A) CH2–CH–CH2OCH3 (B) CH3O CH2–CH–CH2
O O

14 14
(C) HO–CH2–CH–CH2OCH3 (D) CH3OCH2–CH–CH2OCH3

OCH3 OH

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 JEE Sprint Chemistry

CH3
C–CH2 H2O

18
 A , the product (A) has the structure :
11. In the reaction
CH3 H
O

CH3 CH3 CH3 CH3

18 18
(A) CH3–C–CH2OH (B) CH3–C–CH2 OH (C) CH3–C–CH3 (D) CH3–CH–CH2 OH
18 18
OH OH OH

12. The compound which does not react with sodium is

(A) CH 3 CHOHCH 3 (B) CH 3 OCH 3 (C) CH 3COOH (D) CH 3 CH 2OH
13. Which of the following ethers is not cleaved by concentrated HI even at 525 K ?
OCH3 O
(A) (B)

OCH2CH2CH3
(C) (D)
O

OH
14. Which of the following reactions can be used to prepare CH3 – C – C6H5
O C2H5
+
(A) CH3 – C – C6H5 + C2H5MgBr [ ] H3O

O
+
(B) C2H5 – C – C6H5 + CH3MgBr [ ] H3O

O
+
(C) CH3 – C – C2H5 + C6H5MgBr [ ] H3O

Br
Alc.KOH
(D) CH3 – C – C6H5

C2H5
15. What are the products expected in the following reactions ?
O O
CH2N2
C6H5 – C – CH2– C – CH3
Ether
OCH3 O O OCH3

(A) C6HC
5 = CH – C – CH3 (B) C6HC
5 – CH = C – CH3

OCH3 O O OCH3

(C) C6H5– C – CH – C – CH3 (D) C6H5– C – CH – C – CH3

CH2 CH2

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 JEE Sprint Chemistry

16. Which of the following groups will increase the acidity of phenol?
(A) – NO2 (B) –CN (C) –X (halogen) (D) None of these
17. In the esterification of propanoic acid with methanol in the presence of a mineral acid, which of the
following are intermediate species?

OH OH OH OH

(A) C2H5– C – OH (B) C2H5– C – OH (C) C2H5– C – OH (D) C2H5– C – OCH3

OCH3

18. The intermediate stages in the conversion

dil.H2SO4
(CH3)2– C – C – (CH3)2 CH3COC (CH3)3 are

OH OH

(A) (CH3)2– C – C(CH3)2 (B) (CH3)2– C – C(CH3)2

OH OH2 OH

(C) CH3 – C – C(CH)

33 (D) CH3 – C – C(CH)
33

OH OH
19. An alcohol, on treatment with P + I2 followed by the reaction of the formed product first with AgNO2 and
then with HNO2 and final basicification, gives a blue colour. Which of the following alcohols can it be?
(A) CH 3 CH 2OH (B) (CH 3) 2CHOH

CH3
(C) (CH3)3C – OH (D) CHOH
C2H5

20. Which of the following will result in the formation of an ether?

–  – 
(A) (CH 3 ) 3 C ON a + CH3CH2Br (B) (CH3)3CBr + C 2 H 5 ON a

– 
(C) C6H5ONa + CH3Br (D) C6H5Br + CH 3 ON a

ANSWER KEY
Q u e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
An s . C A C D B A B B B B A B B A,B,C A,B
Q u e. 16 17 18 19 20
An s . A ,B,C A ,B,C,D A,B,C ,D B,D A ,C

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 JEE Sprint Chemistry

Carbonyl Compounds


3. (x) OH
  -hydroxy ketone
O H 2O

1. OH
 (P) major product (x) can’t be
H 2O
O O

Stucture of (P) is
(A)
OH
OH O

(A) (B)
O
O O
(B) O
OH

O O
(C) (D)
(C)
O O

OH (D)
2. (x) dil
.NaOH

 (x) is H—C—H
C — CH3
O
O
O 4. O dil
.KOH


(A) O
(P) major product
O O

(B)
OH

OH
O (A) (B) C — CH3

O
O
(C)
O
OH
O
H3C
(C) (D) None
OHC
(D)
O

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 JEE Sprint Chemistry
O
dil.KOH
5.   (x)
O O 
9. (x) + (y) dil
.NaOH


major product structure of (x) is 

O O (x) and (y) are

O O
OH CHO
(A) (B)
(A) and

HO O O

COH
CHO
(C) (D) (B) and

O O

CH3
6. Aldol addition can be
(C) and
(A) Acid catalysed (B) Base catalysed
(C)Acid promoted (D) A and B both (D) None

O
O

dil. KOH H Ag

7. (x)  Structure of (x) is 10. 2 O
. NH 4 OH
 (p)
HO
Product (P) is
O
O
O
(A) (B) (A) OH

OH
OH
(C) (D) (B)
OH
HO
O

O (C) OH
8. + O
Dil
.KOH


HO
O
Total number of aldol condensation products
are (excluding stereoisomer)
(A)2 (B)3 (D) H

(C)4 (D)5 O

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 JEE Sprint Chemistry
O O

11.
OH (x) O 16. (
i ) Dil NaOH
  Product
 ( ii ) 

Reagent (x) is Degree of unsaturation in product is?

(A) PCC (B) CrO3,H2SO4,H2O (A) 2 (B) 3
(C) Ag2O,NH4OH (D)All (C) 4 (D) 5

COOH O
CHO
— CH3
12. (CHOH)4 (CHOH)4

HO

17. heat C.Compound (C) is:
CH2OH (Re tro )
CH2OH
OH
Reagent responsible for given conversion will
be
O
(A)Ag2O,NH4OH (B)Br2,H2O
(C) Cu+2 (D)All O
C — CH3
13. Conc . NaOH
HCHO   (x) + (y)
(A) (B)
(i) Oxidation number of carbon changes from
(A) O to +1 and 0 to –2 O
(B) 0 to +1 and 0 to –1
O O
(C) 0 to +2 and 0 to –2
(D) None
(ii) Given reactin is an example of (C) (D)
(A) oxidation (B)Reductopn
(C)both (D)None

14. Compound which gives cannizaro reaction? 18. This is an example of an intramolecular aldol
(A)CD3CHO (B) C6H5CHO O

O
(C)CH3COCH3 (D)
reaction: H
2SO 4
 (A),
H 2O
O
15. Compound which gives intramolecular aldol re-
action?
Product (A) is:
O
(A) O O

O O
(A) (B)
(B)
O
O

(C) (D)

(C) (D) B and C both

O

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 JEE Sprint Chemistry
19. Which acid can be oxidised be Fehling solu-
O3
tion: 22.  (A) Conc . KOH
Zn  
(A) Malonic acid (B) Acetic acid
(C) Oxalic acid (D) formic acid H
(B)  (C) ; Product (C) is


O
e lodoform test
+iv

20. C6 H12 O3 –i v
e Tollens test H
2O
  O
O
drop of H 2SO 4
A (A) (B)
O
Positive Tollen’s Test Compound (A) is : O

O O OCH3
O
(A) CH3– C – CH 2– CH3 (B) CH3 – C – C – CH3 (C) (D)
O
OCH3
(1) O3 / Zn 
O 23. (A) ( 2 ) conc. KOH
  
 OH + HC O2 K

(C) CH3 – C – CH2 – CH – OCH3

HBr (B) major
OCH3 CCl4
Product (B) is
O

(A) (B)
(D) H– C – CH2– CH 2– CH – OCH3
Br Br
OCH3

(C) (D)
O
O
Mel excess
21.  81% yield; Product of the
KH excess

24. (A) KOH


reaction is
O O
HCHO
(B) ; Product (B) is
KOH,
(A) (B)
O O

O
O (A) (B)

O
(C) (D)

(C) (D)

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 JEE Sprint Chemistry
29. Arrange these compounds in decreasing order
OH
of reactivity for the nucleophilic addition reac-
KCN tion:
25. (A) 
 ; Product (B) is
H (l) Acid chloride (ll) Aldehyde
CN
(lll) Ketone (lV) Ester
Select the correct answer from the codes given
below:
Ph–CH=O (A) l > ll> lll > lV (B) lV > lll > ll > l
(B)
KOH,  (C) lll > ll > l > lV (D) l > lV > ll > lll
(A) Ph – CH = CH – Ph
(B) Ph – CH = CH – CH = O 30. Acetal or ketal is:
(A) Vic dialkoxy compound
(C) (D) (B)  ,  -dialkoxy compound
Ph
(C)  -alkoxy alcohol
(D) Gem dialkoxy compound
26. (A) Positive

tollen 's test
O

Na 2 CO 3
31.   Product (A) is
Ph–CH=O 
(B) ; Product (B) is

(A) Ph – CH = C – CH3 O O

O CH3
CH3 (A) (B)

(B) CH–Ph (C) Ph – C =CH –Ph

O O

(D) Ph – CH = CH – CH = O OH
(C) (D)
27. Gem dilhalide on hydrolysis gives:
(A) Vic diol (B) Gem diol
32. In the given reaction:
(C) Carbonyl compound
(D) Carboxylic acid C

Na OH / H
28. Ph – CO2H + CH3CO2H C6H5– O–H 2   [x] , [x] will be:

CaO/ (A) Only syn oxime

(B) Only anti oxime
O O (C) Mixture of syn and anti oxime
(D) Secondary amide
(A) Ph–C–Ph (B) Ph – C – CH3
O 33. Schiff’s base is prepared from:
(A) Carbonyl compound and primary amine
(C) (D) All
(B) Carbonyl compound and secondary amine
(C) Carbonyl compound and tertiary amine
(D) All of these

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 JEE Sprint Chemistry
34. Schill’s reagent is used for the differentiation O
between:
(A) HCHO and CH3CHO 37. D– C –D 50
% 
KOH
 Order of the reaction is :
(B) CH3COCH3 and CH3CHO
(A) 2 (B) 3
O O (C) 4 (D) 1

38. In the reaction

(C) C6H5 – CH2 – C – CH3 and C6H5 – C –CH2–CH3 HO

NaOH
(D) HCHO and C6H5CHO X+ Y   CH3– CH—CH – CHO
5 C

35. I n the reaction sequence[ X] is ketone: CH 3

(X) and (Y) will respectively be:

[ X] KMnO
 4 /
OH / 
 HOOC – (CH2)3–CH2–COOH (A) CH3–CH2–CHO and CH3–CH2–CHO
(B) CH3–CHO and CH3–CH2–CHO
[X] will be: (C) CH3–CHO and CH3–CHO
CH3
O O

CH3 (D) CH3–CHO and CH3–C–CHO

(A) (B)
CH3

O O 39. Total number of products in the given reaction

: (excluding steroisomers)
H3C 
CH3 CH3 OH
(C) (D) C6H5CHO+CH3–CHO  Product will be

(A) One (B) Three
(C) Two (D) Four

36. In the given reaction 40. In the reaction:

O O O 
+ O
H/
 [X] will be
O
SeO
 2  [x] OH OH OH

[X] will be : (A) (B)

O O
O O O
CHO
(A) (B) OH
(C) (D)

O
O
41. Product of Perkin reaction is :
CH3
(A) ,  -unsaturated aldehyde
CH3
(C) (D) (B)  -cyclohexyl ,  -unsaturated aldehyde
O
O (C)  -Aryl- ,  -unsaturated acid
(D) All of these

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 JEE Sprint Chemistry
42. The product of the reaction: 46. Cyanohydrin of which compound on hydrolysis
will give lactic acid?
NO2 CHO+(C6H5–CH2CO)2O
(A) C6H5CHO (B) HCHO
C6 H—CH
5 2 COONa/ 
(C) CH3CHO (D) CH3–CH2–CHO
[X]
[X] will be:
(A) C6H5 – CH = CH –COOH 47. Acetaldehyde cannot give:
(A) lodoform test (B) Lucas test
(B) NO2 CH = CH–COOH
(C) Benedict test (D) Tollens test
(C) C 6H 5–CH=C–COOH

OCH2CH3

48. Compound formed by the

NO2 O CHOH

(D) NO2 CH=C–COOH

C 6H 5
reaction of furfural O with ethanol is
CHO
43. Cross cannizzaro reaction is example of
(A)Redox reaction
(A) an aldol (B) an acetal
(B) Disproportionation
(C) Both (A) and (B) (C) a ketal (D) a hemiacetal
(D) Only oxidation

44. Which will give silver mirror test with Tollens

O3
reagent: 49.  (A) Conc
 . KOH
 (B), Product (B) is:
Zn
(A)C6H5CHO (B) CH3–CHO
(C) HCOOH (D) All of these
(A) CH2–OH (B) CO 2H
O CH2–OH CO 2H
P2O 5 CH MgBr
45. C NH2  W 3 

X (C) CH2–OH (D) CO 2
 H 3O
CO 2 CO 2
Ca ( OH ) 2 .l 2
  Y   Z, Z is :
 yellow ppt . y   50. Which of the following will reacts with NaOI ?
O
O
O
(A) C – CH3

(A) CH3 – C – H (B)

O
(B) COOH

O O

(C) (C) (D) All

C

(D)

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 JEE Sprint Chemistry

O NaH,CH3 I Cl
(P)
O=S=O
51.
LDA,CH3 I
(Q) 53. CH3O18H +  (A) CH
 O
3

 (B) Product (B) is

CH3
Product (P) and (Q) respectively is:

O O
O

(A) (A) CH3–O– S CH 3

O O O

18
(B) CH3 – O – S CH 3
(B)
O

18
(C) CH3– O –CH3 (D)CH3–O–CH3
O O

O
(C)
54. A KOH



 
O O
B KOH
 PH–CH2OH+Ph–C O 2 K


When A reacts with B in presence of KOH /

(D)
 product C is formed product C is ?
(A)Ph–CH=CH–CHO
O
52. Which of the following compound not reacts
with NaHSO3? (B) Ph–CH2–CH2– C –CH3

O O O

(A) H – C – H (B)CH3 – C – H
(C) Ph–CH= CH – C –CH3

O O (D) None

(C) (D)

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 JEE Sprint Chemistry

55. Ph –CH= O+ NH2–NH2 

H (A). Product (A) is
O3 KOH
known as: 58.  (A) 
Zn 

(A) Aldo-Oxime (B) Hydrazone

(B)Major product (B) is:
(C) Hydrate (D) Phenyl hydrazone

O O

56. HO–CH2–CH2–CH=O (

1) KCN
 (A), Product (A) is:
(2) H
( 3) H 3 O 
(4)  (A) (B)

OH
O
O O O
(A) OH (B)
O
O
(C) (D)

O
O
O O
(C) (D) O O
OH OH
59. CH3 – C – CH3 + H – C – H KOH

O O
(A) major. Product (A) is :
57.
2eq.KNH2
  n
 C 4 H 9  Br
 
 (P) O
NH3 (  ) then H 3O O

(A) (B)
End product (P) of above reaction is:

O O O O O HO

(C) (D) O
H
(A) (B)

O
O O O O
60. CH3 – C –OH CaO
 (A) KOH
 
 

(C) (D)
D 2 O / DO 
  (C)
(B) prolonged treatment 

How many hydrogen is replaced by Deuterium

(A) 2 (B) 10
(C) 7 (D) 8

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 JEE Sprint Chemistry
O 62. Product P is .

61. ( i ) KCN

 P OEt
( ii ) H 3O  OEt
H OEt
(A) (B)
Find out the incorrect statement about the OEt
above given reaction
(A) It is a nuclephilic addition reaction
OMe OMe
(B) Obtained product is present in racemic mix-
OPr
ture (C) (D)
(C) If the hydrolysis of obtained product OPr
give  -hydroxy acid
(D) It is a electrophilic addition reaction
63. Product Q is .
Comprehansion : (Q.62 to Q.64):
Aldehydes and ketones react with one mol- O
ecule of an alcohol to form compounds called (A) (B) O
hemiacetals, in which there is one hydroxyl
group and one ether-like group. Reaction of a
hemiacetal with a second molecule of alcohol O
gives an acetal and a molecule of water. We
(C) O (D)
study this reaction

HO
ROH ROH
OR
   
O

H OR H OR
The carbonyl A hemiacetal An acetal 64. Product R is .
group of an (has an—OH and (has two —OR
aldehyde of ketone an—Or group to groups to the
the same carbon) same cabon)
O
O
Draw structural formulas for the hemiacetal and O
(A) O (B)
acetal formed from these reagents. The sto-
ichiometry of each reaction is given in the prob-
lem.

O 
(A) H
+2 CH3CH2OH  (P)
(C) (D)
Cyclohexanone Ethanol

O 
(B) +HOCH2CH2OH H (R)


Cyclohexanone Ethylene glycol

HO O

(C) + H (Q)
HO 

cis-1,2-Cyclohexanediol Acetone

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 JEE Sprint Chemistry

Answer Key

1. B 2. C 3. D 4. B 5. D 6. D 7. B
8. C 9. D 10. C 11. A 12. D 13.(i)C(ii)C 14. B
15. D 16. B 17. A 18. A 19. D 20. C 21. C
22. A 23. B 24. B 25. B 26. D 27. C 28. D
29. A 30. D 31. A 32. C 33. A 34. B 35. A
36. B 37. B 38. B 39 C 40. D 41 C 42. D
43. A 44. D 45. C 46. C 47. B 48. D 49. C
50. D 51. C 52. D 53. D 54. C 55. B 56. A
57. D 58. B 59. C 60. B 61. D 62. B 63. B
64. B

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 JEE Sprint Chemistry
Carboxylic acid and Derivatives
SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER)

1. Acids have much higher boiling points than isomeric esters because :-
(A) Acids form dimers by H–Bonding
(B) Acids are volatile in steam
(C) Ester are non–volatile
(D) Acids can ionise to give protons in aqueous solution
2. Which of the following acids have the lowest pK a value :-

Cl

(A) CH3 CH COOH (B) Cl CH2 CH2 COOH

(C) CCl3COOH (D) CHCl 2COOH

3. The reaction of an amide with bromine and alkali to form a primary amine is called :-
(A) Hunsdiecker reaction (B) Hofmann mustard oil reaction
(C) Hoffmann degradation of amides (D) Hell–Volhard–Zelinski reaction
4. The regents A and B in the reaction sequence

A
CH3COOC2H5  CH3COOC(CH3)3

B
CH3CONHNH2

are given by the set :-

(A) Isopropyl alcohol, hydrazine (B) Isopropyl alcohol, hydroxylamine
(C) t-butyl alcohol, hydrazine (D) t-butyl alcohol, hydroxylamine
5. The carboxylic acids react with hydrazoic acid in presence of H 2SO 4 to form a primary amine. This reaction is
called as :-
(A) Curtius rearrangement (B) Lossen rerrangement
(C) Schmidt reaction (D) Schotten-Boumann reaction

CH MgBr 
H3O
6. Ethyl acetate  3
Excess
  P

The product P will be :-

H3C CH3 H3C C2H5 H5C2 C2H5 H5C2 C2H5

(A) (B) (C) (D)
H3C OH H5C2 OH H5C2 OH H7C3 OH

7. HVZ reaction is specific for –

(A) Replacement of –hydrogens (B) Replacement of –hydrogens

(C) Replacement of – carbons (D) Replacement of – carbons

8. Decreasing order of acidity of p-methoxy benzoic acid (A), p-nitrobenzoic acid (B) and benzoic acid
(C) is–

(A) B, C, A (B) A, B, C (C) C, A, B (D) None

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 JEE Sprint Chemistry

9. Benzoic acid reacts with Ca(OH) 2. The product obtained on dry distillation gives–

(A) Benzophenone (B) Acetophenone (C) Benzaldehyde (D) None of these

10. In a set of the given reactions, acetic acid yielded a product C.

C H ( i ) C H MgBr / ether
CH 3COOH+PCl 5  A   B 
AlCl 3 
6 6 2 5


 C ; product C would be:-
(ii ) H 3 O

C2H5

(A) CH3CH(OH)C2H5 (B) CH3COC6H 5 (C) CH3CH(OH)C6H5 (D) CH3 C(OH)C6H5

11. The correct reactivity order with the nucleophile is :

(A) CH3COCl > CH3CONH2 > CH3COOCH3
(B) CH3COCl > CH3COOCH3 > CH3CONH2
(C) CH3CONH2 > CH3COOCH3 > CH3COCl
(D) CH3COOCH3 > CH3COCl > CH3CONH2

12. CH3 CH2 C NH2 

A
  CH3—CH2—NH2

B
    CH3—CH2—OH
O

In the above sequence A & B respectively are -

(A) Br2/KOH, NaOH (B) Br2/KOH, HNO2 (C) KMnO4 , KOH (D) HNO2, Br2 / KOH
13. Ethyl acetate on treatment with hydrazine gives -

(A) CH3 C NH.NH2 (B) CH3 C OC2H5 (C) CH3 C ONH.NH2 (D) CH3 C NH2
O N.NH2 O O

14. Among the following, which is the strongest acid?

(A) CHF2 – CH2– CH2–COOH (B) CH3– CH2 – CF2 – COOH
(C) CH2F –CHF – CH2 –COOH (D) CH3– CF2 – CH2 – COOH
15. In the Rosenmund reduction, the catalyst used is:
(A) Pd/ BaSO4 (B) Raney Ni (C) Sn/HCl (D) Zn/HCl
16. Which of the following carboxylic acids undergoes decarboxylation easily?

(A) C6H5COCH2COOH (B) C6H5COCOOH (C) C6H5CH COOH (D) C6H5CHCOOH

OH NH2

17. The reactivities of acid halides (I), anhydrides (II), esters (III) and amides (IV) with nucleophilic reagents follow the
order
(A) I > II > III > IV (B) IV > III > II > I (C) I > III > II > IV (D) III > II > I > IV
18. In the following sequence of reactions

AlCl3 Zn (Hg)
+ CH3CH2COCl A B
conc. HCl, Heat

the product (B) is:

(A) PhCOCH2CH3 (B) PhCHOHCH2CH3 (C) PhCH2CH2CH3 (D) PhCH= CHCH3

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 JEE Sprint Chemistry

19. Consider the following reaction.

O O
(i) NaBH4
+ A
(ii) H ,
OCH3
The product (A) is :

OH O
OH
(A) OH (B)
OH

(C) (D)
O O O

20. Which of the following orders regarding the base strength of a leaving group in a reaction of an acid derivative
with a nucleophile is correct :
(A) Cl  > RCOO  > RO  (B) Cl  > RO  > RCOO 
(C) RO  > RCOO  > Cl  (D) RO  > Cl  > RCOO 
21. The correct sequence of decreasing order of reactivity of hydrolysis of acid chlorides is :
(A) PhCOCl > p-O 2NC 6H 4COCl > p-CH 3OC 6 H 4COCl
(B) PhCOCl > p-CH 3OC 6H 4COCl > p-O 2 NC 6H 4COCl
(C) p-O 2NC 6H 4COCl > PhCOCl > p-CH 3OC 6 H 4COCl
(D) p-O 2 NC 6H 4COCl > p-CH 3OC 6H 4COCl > PhCOCl
22. Kolbe electrolysis of potassium succinate gives CO 2 and ................. :
(A) C 2H 6 and KOH (B) C 2H 2 and KOH
(C) C2H 4, KOH and H 2 (D) CH 4, C2H 6 and C 2H 4
23. In the following reaction identify compounds A, B, C and D :
PCl 5 + SO 2  A + B ;
A + CH 3 COOH  C + SO 2 + HCl
2C + (CH 3) 2 Cd  D + CdCl 2
(A) SOCl2, POCl3, CH3COCl, CH3COCH 3 (B) SOCl 2, HCl, CH 3Cl, CH 3CHO
(C) SO2, Cl2, C2H5Cl, CH3COCH3 (D) None of these
24. What are A and B in the following sequence of reactions :

P ( i ) Alc.KOH excess
(i) CH3CH2COOH 
Br2
A ; (ii) A  (ii ) H 

B

(A) CH3—CH.COOH, CH2 = CHCOOH (B) CH 3CH 2COBr, CH 2 = CHCOOH

Br
Br
(C) CH2CH2COOH, CH2 = CH.COOH (D) H3C——–COOH, H2C=C—COOH
Br Br Br

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 JEE Sprint Chemistry

25. Which of the following compound would be expected to decarboxylates when heated :-

O O O O
(A) (B)
H3C OH H3C CH3

O O O O
CH3 OH
(C) H C (D) H3C
3
O CH2

ANSWER KEY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
An s . A C C C C A B A A D B B A B A A A C C C
Qu e. 21 22 23 24 25
An s . C C A A A

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 JEE Sprint Chemistry

Level–2
SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS)

1. Which of the following reactions involve a decrease in the length of the carbon chain :-
(A) Schmidt reaction (C) Hofmann's bromamide reaction
(C) Hell-Volhard-Zelinski reaction (D) All of these

2. Dry distillation of a mixture of calcium formate and the calcium acetate gives –

(A) HCHO (B) CH 3CHO (C) CH3COCH3 (D) None

3. Consider the following sequence of reactions.

HOCH2.CH2OH 1. LiAlH4,Et2O
A + B
H+ 2.H3O

COOCH3
The products (A) and (B) are, respectively,

O OH O
O O

(A) and (B) and

O
CH3OC COOCH3 COOCH3
COOCH3
O

O HO OCH2CH2OH OCH= CH2

O O

(C) and (D) and

CH2OH COOCH3 CH2OH

COOCH3

4. Consider the following reaction.

CH2COOH
1. B2H6, THF
+
A
2.HO
3
O2N

The product (A) is

CH2CH2OH CH2CH2OH
(A) (B)

O2N H2N
CH2CHO CH2COOH

(C) (D)
O2N H2N

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 JEE Sprint Chemistry

5. Which of the following methods are used for the conversion of carboxylic acids into acid chlorides
(RCOOH  RCOCl) ?
(A) RCOOH + SOCl2  (B) RCOOH + PCl5 
(C) RCOOH + Cl2  (D) RCOOH + P + Cl 2 
6. Which of the following statements are correct for benzoic acid ?
(A) Nitration gives o-and p-nitrobenzoic acid.
(B) Bromination (Br 2/FeBr 3) gives m-bromobenzoic acid.
(C) The Friedel-Crafts reaction with CH 3COCl/AlCl 3 gives m-carboxyacetophenone.
(D) The reaction with concentrated sulphuric acid gives 3-carboxybenzenesulphonic acid.
7. Which of the following compounds react with aniline to give acetanilide :
Which of the following compounds react with aniline to give acetanilide.
O
–NH2 –NHCCH3

Aniline Acetanilide
O O O
(A) CH3COCl (B) H C O CH3 (C) CH3CHO (D) –OCCH3
3

8. What is the final product (B) of this sequence :

CH3
Br2 1.KCN
A B
light 2. H3O+ ,Heat

CH3 COH
2
CH3 CH2CO2H
CO2H
(A) (B) (C) (D)
CO2H

9. What is compound Z :

NaCN H3O 3 2  CH CH OH
CH3CH 2CH 2Br   X  Y 
H
Z

O
(A) CH3CH=CHCOH (B) CH 3CH 2CH 2CH=NOCH 2CH 3
O
(C) CH3CH2CH2CH(OCH2CH3)2 (D) CH3CH2CH2COCH2CH3

O
CH 3 OH
10.   A , A is :
O

(A) CH2—CH2 (B) CH2— CH2 (C) Both are correct (D) None is correct
OH COOCH3 COOH OCH3

11. Which of the following orders of acid strength is correct :

(A) RCOOH > ROH > HOH > HCCH (B) RCOOH > HOH > ROH > HCCH
(C) RCOOH > HOH > HCCH > ROH (D) RCOOH > HCCH > HOH > ROH

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 JEE Sprint Chemistry

12. The relative order of esterification of alcohols is :-

(A) 1° < 2° < 3° (B) 1° > 2° > 3° (C) 1° > 3° > 2° (D) 1° < 3° < 2°
13. The treatment of CH 3CH 2COOH with chlorine in the presence of phosphorus gives :
(A) CH3CH2COCH3 (B) CH3CH 2CH 2Cl (C)CH3CH(Cl)COOH (D) ClCH2CH 2COOH
14. Which of the following sequences of rate of alkaline hydrolysis of esters is correct :
(A) CH3CH 2COOCH3 < (CH 3)2CHCOOCH3 < (CH 3) 3CCOOCH 3
(B) CH3CH 2COOCH 3 > (CH 3) 2CHCOOCH 3 > (CH 3)3CCOOCH 3
(C) CH3CH 2COOCH 3 > (CH 3) 2CHCOOCH 3 < (CH 3)3CCOOCH 3
(D) CH3CH 2COOCH 3 < (CH 3) 2CHCOOCH 3 > (CH 3)3CCOOCH 3
15. Which of the following is used to perform following transformation :

Cl
OH H3C
H3C
O
O

(A) SOCl2 (B) PCl 5 (C) PCl3 (D) SO 2Cl 2

16. Which of the following does not give iodoform :
(A) Acetic acid (B) lactic acid (C) Actophenone (D) propionic acid
17. One can distinguish between HCOOH and CH 3COOH with :
(A) NaHCO 3 (B) H2SO 4 (C) tollens reagent (D) fehling's solution
18. Which of the following reagents are involved in the following transformation ?

O O
OR OH
+ ROH
O

(A) H 3O + (B) LiAlH4 (C) Ethylene glycol (D) Acetone

19. Cl KCN H3O  

(A )  (B)  (C)
Cl

Identify the correct statement(s) about the above sequence of reactions :

(A) Compound (A) is formed through S N reaction
(B) Compound (C) on reduction with LiAIH 4 forms a product which on dehydration given cyclohexene.
(C) compound (A) requires two moles of hydrogen for complete reduction.
(D) Compound (C) on Schmidt's reaction gives a product which reacts with HNO2 to give (D) as major product.
Compound (D) on dehydration gives cyclopentene
20. Which of the following on reduction with LiAIH4 will give ethyl alcohol ?
(A) (CH3CO)2O (B) CH3COCl (C) CH3CONH2 (D) CH3COOC2H 5

ANSWER KEY
Q u e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
An s . A ,B A ,B,C C A A,B,D B,D A ,B,D D D A B B C B A ,B,C
Q u e. 16 17 18 19 20
An s . A,D C,D A,B,C A ,B,D A,B,D

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 JEE Sprint Chemistry
Amines
SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER)
1. Tertiary butyl amine is a
(A) 1° Amine (B) 2° Amine
(C) 3° Amine (D) Quaternary salt
2. The correct set of the products obtained in the following reactions

 i  CH MgBr
 (A) , RCN  
 (B), RNC 
3 hydrolysis HNO2
reduction
RCN   ii  H2O  (C), RNH2   (D)

The answer is :
A B C D
(A) 2°Amine Methyl ketone 1° Amine Alcohol
(B) 1°Amine Methyl ketone 1° Amine Alcohol
(C) 2°Amine Methyl ketone 2° Amine Acid
(D) 2°Amine Methyl ketone 2° Amine Aldehyde
3. Which one of the following tests can be used to identify primary amino group in a given organic compound
(A) Iodoform test (B) Victor Meyer's test
(C) Carbylamine reaction (D) Libermann's reaction

CO
KOH
NH  C 2 H 5 Br HOH
4. A   B 
H
 C + D
CO

C and D in the above sequence are

(A) Benzoic acid + aniline (B) Phthalic acid + ethylamine
(C) Phthalic acid + aniline (D) Benzoic acid + ethylamine
5. Lowest boiling point will be of the compound
(A) 2-propanamine (B) Ethylmethylamine
(C) 1–propanamine (D) N, N–dimethylmethanamine
6. How many primary amines can be formulated by C3H9N and how many 1° hydrogen are associated with
carbon atoms of each compound
(A) Two primary amines [3, 6] (B) One primary amine [3]
(C) Three primary amines [3, 6, 6] (D) Two primary amines [5, 6]
7. Identify B, X and R respectively in the following sequence of reactions

ClCN H3O 
C2 H 5MgBr  
 A   B ,

I Ag
CH 3COCH 3 
2
X   Y
NaOH

NaNO 2 CuCN 4 H
C 6 H 5 NH 2 
HCl  P   Q  R

(A) C 2 H 5 COOH, CHI 3 , C 6 H 5 CH 2 NH 2

(B) C 2 H 5 COOH, CH 3 I, C 6 H 5 COOH
(C) C 2 H 5 CH 2 NH 2 , CH 3 I, C 6 H 5 COOH
(D) C 2 H 5 COOH, C 2 H 5 I, C 6 H 5 CONH 2

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 JEE Sprint Chemistry

HNO2
a
C6H5CHO
b
C2H5NH2 
8. NOCl
c
C6H5SO2Cl
d

Which product is a Schiff's base :-

(A) a (B) b (C) c (D) d
9. A + CS2 + HgCl2 gives C2H 5—N C S. Thus compound A is :-
(A) C2H5NH2 (B) C2H5NHC2H5 (C) CH 3—CH NOH (D) CH3CH 2NO 2
10. The end–product in the reaction sequence would be :

HNO2 PCl5 NH 3
Ethyl amine   A   B  C
(A) Ethyl cyanide (B) Ethyl amine (C) Methyl amine (D) Acetamide
11. In the reaction sequence :-
SnCl2 / HCl NaNO2 / HCl H2 O / 
A   B 
0  C   C6H5OH, A, B and C are :-

(A) Benzene, nitrobenzene, aniline (B) Nitrobenzene, aniline and azo–compound

(C) Nitrobenzene, benzene, aniline (D) Benzene, amino compound, aniline
12. Methylamine on treatment with chloroform and ethanolic caustic alkali gives foul smelling compound, the
compound is
(A) CH 3 NCO (B) CH 3 CNO (C) CH 3 CN (D) CH 3 NC
13. Which of the following is used as a solvent in the Friedel–Crafts reaction :-
(A) Toluene (B) Nitrobenzene (C) Benzene (D) Aniline
NaOH
14. CH 3 CH 2 CONH 2 
Br2
 A,

Aqueous solution of A
(A) Turns blue litmus to red (B) Turns red litmus to blue
(C) Does not affect the litmus (D) Decolourise the litmus
15. Hinsberg reagent is used to distinguish between

(A) — CHO, C O (B) — CH2OH, CHOH, C OH

(C) —O—, —OH (D) —NH 2 , —NH—, N

16. Reactants of reaction – I are : CH 3CONH 2, KOH, Br 2

Reactants of reaction–II are : CH 3 NH 2 , CHCl 3 , KOH
The intermediate species of reaction–I and reaction–II are respectively
(A) Carbonium ion, carbene (B) Alkyl isocyanate, carbene
(C) Carbene, nitrene (D) Carbocation, carbanion
17. Which of the following amine does not respond to carbylamine reaction :-
(A) Ethylamine (B) (CH 3 ) 2 NH (C) CH 3 NH 2 (D) Phenylamine

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 JEE Sprint Chemistry
18. (a) CH3CONH2 + KOH + Br2 
(b) CH3COOH + soda lime 
(c) CH3COOAg + Br2 
All the three reactions show similarity in -
(A) Descending of carbon atoms (B) Ascending of carbon atoms
(C) Both the above (D) None of the above
19. Which of the following reagents can convert benzenediazonium chloride into benzene ?
(A) Water (B) Acid (C) Hypophosphorous acid (D) HCl
20. Hofmann's method to separate amines in a mixture uses the reagent :-
(A) Benzenesulphonyl chloride (B) Diethyl oxalate
(C) Benzeneisocyanide (D) p–toluenesulphonic acid
21. Which of the following compounds will dissolve in an alkali solution after it has undergone reaction with
Hinsberg reagent ?

(A) (C 2 H 5 ) 2 NH (B) CH3 N C6H5 (C) CH 3 NH 2 (D) C 6 H 5 NHC 6 H 5

CH3

22. The number of resonating structures of aniline is :-

(A) 2 (B) 3 (C) 4 (D) 5
23. How many isomeric amines with formula C 7H 9 N contain a benzene ring ?
(A) Two (B) Three (C) Four (D) Five
24. Reaction of RCONH2 with a mixture of Br2 and KOH gives RNH2 as the main product. The intermediate
involved in the reaction is :-

O O Br
(A) R C NHBr (B) R – NHBr (C) R C N (D) R – C = N = O
Br

25. The bromination of aniline in water produces :-

(A) 2-bromoaniline (B) 4-bromoaniline
(C) 2, 4, 6-tribromoaniline (D) 2, 6-dibromoaniline

ANSWER KEY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
An s . A B C B D D A B A B B D B B D B B A C B
Qu e. 21 22 23 24 25
An s . C D D A C

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 JEE Sprint Chemistry

Level–2
SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS)

1. Carbylamine test is performed in alcoholic KOH by heating a mixture of :-

(A) Chloroform and silver powder
(B) Trihalogenated methane and a primar y amine
(C) An alkyl halie and a primary amine
(D) An alkyl cyanide and a primary amine
2. Acetamide is treated separately with following reagents. Which one of these would give methylamine ?
(A) PCl 5 (B) Sodalime
(C) NaOH + Br 2 (D) Hot concentrated H 2 SO 4
3. Maximum basic in gas phase is ?
(A) NH 3 (B) CH 3 CH 2 NH 2 (C) (CH 3 CH 2 )NH (D) (CH 3 CH 2 ) 3 N
4. Benzenediazonium chloride on reaction with aniline in weakly basic medium gives
(A) diphenyl ether (B) p-aminoazobenzene (C) Chlorobenzene (D) benzene
5. Which of the following statements is correct ?
(A) Replacement of halogen by NH 2 in alkyl halide is a nucleophilic substitution reaction
(B) Aryl halides show more reactivity as compared to alkyl halides in the replacements of halogen by
the NH 2 group
(C) During the replacement of halogen by –NH2 group, ammonia is taken in large excess so as to avoid
the formation of 2° and 3° amines
(D) Tertiary alkyl halide generally produces alkene instead of the replacement of halogen by NH 2 group
6. Which of the following statements is correct ?
(A) Primar y amines show intermolecular hydrogen bonding
(B) Secondar y amines show intermolecular hydrogen bonding
(C) Ter tiar y amines show intermolecular hydrogen bonding
(D) Amines have lower boiling points as compared to those of alcohols and carboxylic acid of comparable
molar masses.
7. Which of the following statements is correct ?
(A) Aliphatic amines are stronger bases than ammonia
(B) Aromatic amines are stronger bases than ammonia
(C) The alkyl group in alkyl ammonium ion more stabilizes the ion relative to the amine
(D) The aryl group in aryl ammonium ion less stabilizes the ion relative to the amine
8. Which of the following orders regarding the basic strength of substituted aniline is correct ?
(A) p–methylaniline > p–chloroaniline > p–aminoacetophenone
(B) p–methylaniline > p–aminoacetophenone > p–chloroaniline
(C) p–aminoacetophenone > p–methylaniline > p–chloroaniline
(D) p–aminoacetophenone > p–chloroaniline > p–methylaniline

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 JEE Sprint Chemistry
9. Consider the following reaction,

C 6H 5NH 2 + CHCl 3 + KOH  ∆ → H / H2 O
(A)   (B) + (C)

The compounds (B) and (C) are :-
(A) C 6H 5COOH and NH 3 respectively (B) C 6H 5NH 2 and HCOOH respectively
(C) C 6 H 5NH 2 and H 2O respectively (D) None of these
10. CH 3CH 2NH 2 is soluble in :-
(A) Dilute HCl (B) CuSO 4 solution (C) AgNO 3 (D) None of these
11. The end product (Z) of the following reaction is :-

+ – CuCN 
H / H2 O NaOH
N2Cl  (X)   (Y) 
  (Z)
CaO, 

(A) A cyanide (B) A carboxylic acid (C) An amine (D) An arene

12. The increasing order of basicity of RCN, RCH = NR and RNH 2 is :-
(A) RCN < RCH = NR < RH 2 N (B) RNH 2 < RCN < RCH = NR
(C) RCH = NR < RNH 2 < RCN (D) RH 2 N < RCH = NR < RCN
13. Amongst the following, the most basic compound is :-
(A) Benzylamine (B) Aniline (C) Acetanilide (D) p–nitroaniline
14. isocyanide test can be given by :

(A) C2H5NH 2 (B) C 6H5NH 2 (C) C6H5NHC2H5 (D) C6H5CH—NH2

C2H5

(D) II is an acceptable canonical structure

15. In the following compounds

N N N N
H H H
(I) (II) (III) (IV)

the order of basicity is

(A) IV > I > III > II (B) III > I > IV > II
(C) II > I > III > IV (D) I > III > II > IV
16. A positive carbylamine test is not given by :
(A) N, N-dimethylaniline (B) 2, 4-hyroxyazobenzene
(C) N-methyl-o-methylaniline (D) p-methylbenzylamine
17. Among the following, the strongest base is
(A) C6H5NH 2 (B) p-NO 2C 6 H 4NH 2
(C) m-NO 2C 6H 4 NH 2 (D) C 6H5CH 2NH 2
18. Phenyl cyanide on reduction with Na/C 2H 5OH yields
(A) C6H5CH2NH 2 (B) C 6H5NHCH 3

(C) NH2 (D) C 6H 5NH 2

CH3

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 JEE Sprint Chemistry

19. Conisider the following ions

+ +
(I) Me2N N N (II) O2N N N

+ +
(III) H3C O N N (IV) H3C N N

The reactiveities of these ions in azo-coupling reaction (under similar conditions) will be such that
(A) (I) < (IV) < (II) < (III) (B) (I) < (III) < (IV) < (II)
(C) (III) < (I) < (II) < (IV) < (II) (D) (III) < (I) < (IV) < (II)
20. The strongest base among the following is

H2N H2N H2N H2N

(A) C NH (B) C NH2 (C) C O (D) CH OH
H2N H2N H2N H2N

ANSWER KEY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
An s . B C D B A,C,D A,B,D A,C,D A B A ,B,C D A A A,B,D D
Qu e. 16 17 18 19 20
An s . A ,B,C D A B A

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 JEE Sprint Chemistry
Biomolecules and Polymers
SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER)

1. The minimum number of carbon atoms that should be present in a monosaccharite is :

(A) 2 (B) 3 (C) 4 (D) 6
2. Carbohydrates that, on attempted hydrolysis, are not cleaved to smaller carbohydrates are called :
(A) oligosaccharides (B) polysaccharides (C) disaccharides (D) monosaccharides
3. The IUPAC name of the ketotriose is :
(A) 1, 3-dihydroxypropanone (B) 1-3-dihydroxy-2-oxopropane
(C) 2-oxo-1, 3-propanediol (C) dihydroxyacetone
4. The number of chiral centres in the open chain structure of glucose is :
(A) 3 (B) 4 (C) 5 (D) 6
5. Cane sugar on hydrolysis gives :
(A) glucose and galactose (B) glucose and fructose
(C) glucose only (D) fructose only
6. In D-erythrose, the configurations at C-2 and C-3 are respectively :
(A) 2R, 3R (B) 2S, 3S (C) 2R, 3S (D) 2S, 3R
7. Glucose and fructose are :
(A) diastereomers (B) anomers (C) epimers (D) functional isomers
8. Which of the following structures represents -D-glucopyranose?

HOCH2 HOCH2 HOCH2 HOCH2

O OOH O O
(A) HOOH (B) HOOH (C) HO HOOH (D) HO
OH OH
HO OH OH OH OH

9. Sorbitol can be obtained by the reduction of -

(A) sorbose (B) glucose (C) fructose (D) all of these
10. Freshly prepared solution of cane sugar, under the influence of acid catalyst, undergoes change in optical
rotation with laps of time. This phenomenon is called -
(A) mutarotation (B) inversion
(C) racemization (D) optical rotatory dispersion
11. In the formation of osazone derivatives of aldohexoses and ketohexoses, the carbon atom (s) that participate
(s) in the reactions is -
(A) C-1 (B) C-2 (C) C-1 and C-2 (D) C-2 and C-3
12. Glucose gives positive silver mirror test with ammoniacal silver nitrate because it contains -
(A) hydroxyl group (B) aldehyde group
(C) ketone group (D) vicinal diol group
13. Fructose reduces fehling's solution due to the presence of -
(A) hydroxy group (B) aldehyde group
(C) ketone group (D) -hydroxyketone group

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 JEE Sprint Chemistry
14. In the multi-step conversion of an aldose into next higher aldose by Kiliani-Fischer synthesis, the reagent
employed in the first step is -
(A) C 6 H 5 NHNH 2 (B) NH 2 OH (C) Br 2/H 2 O (D) HCN
15. When methyl D-Glucopyranoside is oxidized with periodic acid, how many moles of the oxidizing agent are
consumed per mole of the sugar ?
(A) 2 (B) 3 (C) 4 (D) 5
16. -D-glucose is represented as -

HO HO OH OH
HO OHO O OH
OH HO O
O
(A) (B) (C) HO HO (D)
HO HO OH HO HO OH
HO OH OH

17. The number of carbon atoms and oxygen atoms present in the ring of the D-glucopyranose are respectively:
(A) 5 and 1 (B) 4 and 1 (C) 4 and 2 (D) 3 and 2
18. Glucose is oxidized by nitric acid to give
(A) gluconic acid (B) glucaric acid (C) glucuronic acid (D) glycolic acid
19. D-(–)- Erythrose and D-(–)- threose are separately reduced with NaBH 4 to give the products (A) and (B)
respectively. Which of the following statements is correct about (A) and (B) ?
(A) Both (A) and (B) will be optically active.
(B) Both (A) and (B) will be optically inactive.
(C) (A) will be optically inactive but (B) will be optically active
(D) Neither (A) not (B) possesses any asymmetric carbon atom.
20. The products expected from the reaction are :

CHO

CH2
HIO4
H––C––OH
(excess)
H––C––OH

CH2OH
2-Deoxy-D-ribose

(A) OHCCH 2CHO, HCOOH and HCHO (B) HOOCCHOHCHOHCOOH and HCOOH
(B) HOOCCH 2 COOH, HCOOH and HCHO (D) HOOCCOOH, HCOOH and HCHO
21. Glucose does not react with
(A) C 6 H 5 NHNH 2 (B) NH 2 OH (C) HCN (D) NaHSO 3
22. Which one among the following is a peptide linkage ?

(A) ––C––N–– (B) ––C––O—N–– (C) ––C=NH (D) ––N=C––O––

O H R H R R

23. The pH at which an amino acids carries no net charge is called its :
(A) isoelectric point (B) Inversion point (C) Neutralization point (D) triple point

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 JEE Sprint Chemistry
24. The configurations of the compounds I and II

COOH COOH

H NH2 H NH2

CH3 CH2SH
I II
are respectively
(A) R and R (B) R and S (C) S and S (D) S and R
25. Consider the following sequence of reactions.

O
C
NK 
1. BrCH 2 (CO 2 Et )2 1. PhCH 2 Cl
 A  B
2. C 2 H 5 ONa 2. HCl, H 2 O, heat
C
O
The major final product (B) is
(A) H 2 NCH 2 COOH (B) PhCH(NH 2 )COOH

(C) PhCH 2 CH(NH 2 )COOH (D) PhCH2C(COOEt)2

NH2

ANSWER KEY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
An s . B D A B B A D A D B C B D D A A A B C A
Qu e. 21 22 23 24 25
An s . D A A B C

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 JEE Sprint Chemistry
Level-2
SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS)

1. Which of the following carbohydrates is a disaccharide?

(A) Glucose (B) Fructose (C) Maltose (D) Lactose
2. -D-Glucopyranose and -D-glucopyranose are :
(A) Anomer (B) Epimer (C) Diastereomers (D) enantiomers
3. Consider the following structures.
CH2OH CH2OH CH2OH CH2OH
C=O C=O C=O C=O
H OH H OH HO H HO H
HO H HO H H OH H OH
HO H H OH H OH HO H
CH2OH CH2OH CH2OH CH2OH

I II III IV
Which of the following pairs represent D- and L-fructose respectively?
(A) II and I (B) I and III (C) III and IV (D) II and IV
4. (+) - sucrose is made up of -
(A) D-glucose and L-fructose (B) D-glucose and D-frucotse
(C) D-fructose and L-glucose (D) L-fructose and L-glucose
5. Glucose cannot be classified as -
(A) a carbohydrate (B) a hexose
(C) an aldose (D) an oligosaccharide
6. D-Glucose and D-mannose are -
(A) anomers (B) epimers (C) diastereomers (D) enantiomers
7. D-Glucose reacts with anhydrous methyl alcohol in the presence of dry HCl gas to form -
(A) 2,3,4,5,6-penta-O-methyl D-glucose (B) -methyl D-glucopyranoside
(C) -methyl D-glucopyranoside (D) Both (B) and (C)
8. When glucose is treated with an excess of HIO4, the products formed are -
(A) one mole of glyoxal (CHOCHO), one mole of HCHO and three moles of HCOOH
(B) five moles of HCOOH and one mole of HCOH
(C) one mole of oxalic acid (COOHCOOH), three moles of HCOOH and one mole of HCHO
(D) six moles of HCOOH
9. Methyl D-glucoside on reaction with HIO4 consume two moles of the reagent and produces the dialdehyde
(A) and one mole of HCOOH :

HOCH2—CH—O—CH—OCH3
CHO CHO

The result of this reaction proves that glucose has :

(A) a pyranose structure (B) a furanose structure
(C) an open-chain structure (D) a four-membered ring structure

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 JEE Sprint Chemistry

10. Following are the structure of D-glucose and D-galactose-

CHO CHO

H OH H OH
OH H HO H
H OH HO H
H OH H OH
CH2OH CH2OH

D-Glucose D-Galactose
which of the statement is correct about these compounds :
(A) They are diastereomers (B) both are components of lactose
(C) They are C-4 epimers (D) they are enantiomers
11. D-Glucose is treated with an excess of acetic anhydride in the presence of pyridine. Identify the products
formed.

CHO

H OAc CH2OAc
AcO H O
H OAc OAc
(A) (B)
H OAc AcO OAc
OAc
CH2OAc
CHO

CH2OAc OAc H
O OAc AcO H
OAc H OAc
(C) (D)
AcO H OAc
OAc
CH2OAc
12. The product formed in the reaction is :

C 6 H 5 NHNH 2
C 6 H 5 CHOHCOC 6 H 5 
( excess )

C6H5 C6H5 C6H5 C6H5

NNHC6H5 O OH
CHOH C C CH
(A) C (B) C (C) C (D) CH
C6H5 NNHC6H5 C6H5 NNHC6H5 C6H5 O C6H5 OH

13. (+)-Sucrose has a specific rotation of +66.5°, while D-(+)-glucose and D-(–)-fructose have specific rotations
of +52.5° and –92.4° respectively. After complete hydrolysis of (+)–surcose by dilute acid, what will be the
specific rotation of the hydrolysis product, called invert sugar [a 1 : 1 mixture of D-(+)-glucose and
D-(–)-fructose]?
(A) –39.9° (B) –72.4° (C) –19.9° (D) –34.9°

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 JEE Sprint Chemistry
14. Consider the following statements :
(A) Monosaccharides are optically active polyhydroxy carbonyl compounds.
(B) Fructose does not reduce Fehling's solution because it is a ketose.
(C) -D(+)–Glucose and -D(+)-glucose are anomers.
(D) D-Glucose and D-mannose are C-2 epimers.
15. Consider the following statements about sucrose.
(A) Hydrolysis of surcose with dilute acid yields an equimolar mixture of D-gluvose and D-fructose
(B) Acid hydrolysis of sucrose is accompained by a change in optical rotation.
(C) In sucrose, the glycosidic linkage is between C-1 of glucose and C-2 of fructose.
(D) Aqueous solution of sucrose exhibits mutarotation.
16. Alanine, at its isoelectric point, exists in solution as :

 
(A) H 2 NCHCOO  (B) H 3 N CHCOOH (C) H 3 N CHCOO  (D) H 2 NCHCOOH
| | | |
CH 3 CH 3 CH 3 CH 3

17. The pKa of acetylsalicylic acid (aspirin) is 3.5. The pH of gastric juice in human stomach is about 2-3 and
pH in the small intestine is about 8, aspirin will be -
(A) Unionized in the small intestine and in the stomach
(B) Completely ionized in the stomach and almost unionized in the small intestine
(C) Ionized in the stomach and almost unionized in the small intestine
(D) Ionised in the small intestine and almost unionised in the stomach
18. Which of the following are natural polymers ?
(A) proteins (B) cellulose (C) Teflon (D) Natural rubber
19. Amino acids are produced on hydrolysis of :
(A) nucleic acids (B) carbohydrates (C) fats (D) proteins
20. Which of the following do not undergo hydrolysis :
(A) glucose (B) fructose (C) galactose (D) sucrose

ANSWER KEY
Qu e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
An s . C, D A ,B,C C B D B,C D B A A ,B,C B,C B C A,C ,D A ,B,C
Qu e. 16 17 18 19 20
An s . C D A ,B,D D A,B,C

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