CARBONYL COMPOUND

CONTENTS
JEE MAINS
Exercise-I : 2 - 14
Exercise-II : 15 - 27
JEE ADVANCE
Exercise-I : 28
Exercise-II : 29 - 38
Exercise-III : 39 - 45
Answer Key : 46 - 49
 JEE MAINS
EXERCISE-I
–
OH
1. ¾¾ ¾® (P) major product
H O 2

Structure of (P) is

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

2. (x) ¾¾ ¾¾ ¾®
dil . NaOH (x) is

(A) (B)

(C) (D)

–
OH
3. (x) ¾¾ ¾® b-hydroxy ketone
H O2

(x) can't be

(A) (B)

O O
(C) (D)

4. dil . KOH
¾¾ ¾¾® (P) major product

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

[2]
 dil .KOH
5. ¾¾ ¾ ¾® (x) major product
D

structure of (x) is

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

6. Aldol addition can be

(A) Acid catalysed (B) Base catalysed (C) Acid promoted (D) A and B both

7. dil .KOH
(x) ¾¾ ¾ ¾®
D

Structure of (x) is

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

DilKOH
8. ¾¾ ¾¾®

Total number of aldol condensation products are (excluding stereoisomer)

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

dil . NaOH
9. (x) + (y) ¾¾ ¾ ¾¾®
D

(x) and (y) are

(A) and (B) and

(C) and (D) None

10. Ag2 O, NH 4 OH
¾¾ ¾ ¾ ¾¾® (P)

Product (P) is

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

[3]
 +
Br / H
11. ¾¾2 ¾¾® A (major)

(A) CHBr3 (B)

(C) (D)

(i ) LiAlH4
12. ¾¾ ¾¾ ¾® Relationship between products is
(ii ) H2O

(A) Meso (B) Racemic mixture (C) Diastereomer (D) None

13. HCHO ¾¾ Conc . NaOH

¾¾¾ ¾® (x) + (y)
Given reaction is an example of
(A) oxidation (B) Reduction (C) Dispropornation (D) Fermentation
14. Compound which gives cannizaro reaction ?

(A) CD3 CHO (B) C6H5CHO (C) CH3COCH3 (D)

15. Total number of intramolecular aldol condensation products possible from given compound is (excluding
stereoisomer).

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

( i) Dil NaOH
16. ¾¾ ¾ ¾¾® Product
(ii ) D

Degree of unsaturation in product is ?

(A) 2 (B) 3 (C) 4 (D) 5
17. Which acid can be oxidised be Fehling solution:
(A) Malonic acid (B) Acetic acid (C) Oxalic acid (D) formic acid

2 H O
18. ¾¾¾ ¾
¾® Positive Tollen’s Test
drop of H2SO4

Compound (A) is :

(A) (B)

(C) (D)

[4]
19. Ease of reaction is maximum in which of the following cases?

(A)

(B)

(C)

(D) Rate is independent of halogens

O Conc. KOH +
3® H
20. ¾¾
¾ (A) ¾¾ ¾¾ ¾
¾® (B) ¾¾¾® (C) ; Product (C) is
Zn D

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

21.

Product (B) is

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

22. ; Product (B) is

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

[5]
23. ; Product (B) is

(A) Ph – CH = CH – Ph (B) Ph–CH = CH – CH=O

(C) (D)

24.

Product (B) is

(A) (B) (C) (D) Ph–CH=CH–CH=O

25. Gem dihalide on hydrolysis gives:

(A) Vic diol (B) Gem diol (C) Carbonyl compound (D) Carboxylic acid
CaO
26. C6H5 – COOH ¾¾¾®
D

(A) Acetophenone (B) Benzophenone (C) Acetone (D) Benzaldehyde

27. Arrange these compounds in decreasing order of reactivity for the nucleophilic addition reaction :
(I) Acid chloride (II) Aldehyde (III) Ketone (IV) Ester
Select the correct answer from the codes given below:
(A) I > II > III > IV (B) IV > III > II > I (C) III > II > I > IV (D) I > IV > II > III
28. Acetal or ketal is:
(A) Vic dialkoxy compound (B) a, w-dialkoxy compound
(C) a-alkoxy alcohol (D) Gem dialkoxy compound

P O
2¾5 ® (A)
29. ¾¾
D
Product (A) is
(A) (B) Ph – C º N (C) Ph – CH2 – NH2 (D) Ph – CH = NH

NH OH / H Å
30. In the given reaction: C6H5 - C - H ¾¾ 2¾ ¾¾® [X] , [X] will be:
||
O
(A) Only syn oxime (B) Only anti oxime
(C) Mixture of syn and anti oxime (D) Secondary amide
31. Schiff's base is prepared from:
(A) Carbonyl compound and primary amine (B) Carbonyl compound and secondary amine
(C) Carbonyl compound and tertiary amine (D) All of these
32. Schiff's reagent is used for the differentiation between:
(A) HCHO and CH3CHO (B) CH3COCH3 and CH3CHO
O O
|| ||
(C) C 6H5 - CH2 - C - CH3 and C 6H5 - C - CH2 - CH3 (D) HCHO and C6H5CHO
[6]
33. In the reaction sequence, [X] is ketone :
Q
KMnO / O H / D
[X] ¾¾ ¾4¾¾¾® HOOC – (CH2)3 – CH2 – COOH
[X] will be:

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

34. Which of the following ketone / aldehyde can undergoes haloform reaction?

(A) (B) CH3 – CHO (C) (D) All of these

35. Acetone can be converted into pinacol by :

(A) Mg/Hg/H2O (B) Zn/Hg/HCl (C) Na/Hg/H2SO4 (D) All of these
36. In the given reaction

SeO
¾¾¾2 ® [X]

[X] will be:

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

50% KOH
37. ¾¾ ¾¾¾® Order of the reaction is :
(A) 2 (B) 3 (C) 4 (D) 1

38. In the given reaction

OH
|
X+Y ¾NaOH
¾¾® CH3 - CH - CH - CHO
5 °C |
CH3

(X) and (Y) will respectively be :

(A) CH3–CH2–CHO and CH3–CH2–CHO (B) CH3–CHO and CH3–CH2–CHO

(C) CH3–CHO and CH3–CHO (D) CH3–CHO and

39. Total number of products in the given reaction :(excluding stereoisomers)

Q
OH
C6H5CHO + CH3–CHO ¾¾¾® Product
D

will be
(A) One (B) Three (C) Two (D) Four
[7]
 H3OÅ
¾¾ ¾ ¾¾® ¾¾
40. (A) D¾® (B)

Product (B) is

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

41. Product of Perkin reaction is:

(A) a, b -unsaturated aldehyde (B) b -cyclohexyl a, b-unsaturated aldehyde
(C) b-Aryl-a, b-unsaturated acid (D) All of these
42. The product of the reaction:

NO2 CHO + (C6H5–CH2CO)2O

[X]
will be :

(A) C6H5–CH =CH–COOH (B) NO2 CH=CH–COOH

(C) C6H5 – CH=C–COOH (D) NO2 CH = C - COOH

|
C6 H 5

43. Cross cannizzaro reaction is example of :

(A) Redox reaction (B) Disproportionation (C) Both (A) and (B) (D) Only oxidation

44. In the given reaction :

O
||
CH 3 - C - CH 3 ¾Conc
¾¾ ¾
.H 2SO 4
¾® [X]
Distillation
[X] will be :
(A) Methyl oxide (B) Phorone (C) 1, 3, 5-Trimethylbenzene (D) 2-Butyne

45. Which will give silver mirror test with Tollens reagent :
(A) C6H5CHO (B) CH3–CHO (C) HCOOH (D) All of these

O
|| P2O5 CH3MgBr Ca(OH) ,I2
46. C NH 2 ¾¾ ¾® W ¾¾ ¾ ¾¾® X ¾¾ ¾¾2¾ ¾® Y ¾¾® Z ,
D Z is:
D Å ( yellow ppt.+ y )
H3O

O O
|| ||
(A) C - CH 3 (B) COOH (C) C (D)

47. Cyanohydrin of which compound on hydrolysis will give lactic acid?

(A) C6H5CHO (B) HCHO (C) CH3CHO (D) CH3–CH2–CHO

[8]
48. Acetaldehyde cannot give:
(A) Iodoform test (B) Lucas test (C) Benedict test (D) Tollens test

49. Compound formed by the reaction of furfural ( ) with ethanol is

(A) an aldol (B) an acetal (C) a ketal (D) a hemiacetal

3® O Conc. KOH
50. ¾¾
¾ (A) ¾¾¾ ¾¾
¾® (B), Product (B) is :
Zn

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

51. Which of the following will reacts with NaOI ?

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

52.

Product (P) and (Q) respectively is :

(A) (B)

(C) (D)

53. Which of the following compound not reacts with NaHSO3?

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

54.

When A reacts with B in presence of KOH / D product C is formed.

Product C is?

(A) Ph – CH = CH – CHO (B)

||
(C) (D) None

[9]
 Å
55. Ph – CH = O + NH2 – NH2 ¾¾ H
¾® (A). Product (A) is known as :
(A) Aldo-Oxime (B) Hydrazone (C) Hydrate (D) Phenyl hydrazone

O
3® KOH
56. ¾¾
¾ (A) ¾¾¾® (B) Major product (B) is :
Zn D

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

KOH
57. ¾¾¾® (A) major. Product (A) is :

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

CaO KOH
2 ¾ ¾ ¾¾ D O / DOQ
58. ¾¾¾® (A) ¾¾¾® (B) ¾¾¾ ¾ ¾® (C)
D D (prolonged treatment )
How many hydrogen is replaced by Deuterium.
(A) 2 (B) 10 (C) 7 (D) 8

(i) KCN
59. ¾¾ ¾¾® ‘P’
(ii ) H3OÅ
Find out the incorrect statement about the above given reaction
(A) It is a nucleophilic addition reaction
(B) Obtained product is present in racemic mixture
(C) The hydrolysis of obtained product give a-hydroxy acid
(D) It is a electrophilic addition reaction
60. Which of the following compound reduced by NaBH4 ?

(A) (B) CH3 – NO2 (C) (D)

(i ) LiAlH4
61. ¾¾ ¾¾ ¾® Relationship between products is
(ii ) H2O

(A) Meso (B) Racemic mixture (C) Diastereomer (D) None

3 4
62.

Products A and B respectively are

(A) , (B) ,

(C) , (D) ,

[10]
63.

The products A and B respectively are

(A) , (B) ,

(C) , (D) ,

O O O
64. R–C N R–C R–C R–C
Cl OH OEt
(1) (2) (3) (4)
When the compounds 1, 2, 3 and 4 reacted with a specific reagent 'K', the product obtained was RCHO. The
reagent K is/are
(A) H2 / Pt (B) LiAlH4 (C) DIBAL (D) None of the above

65. 2, 4 DNP in used in the test of

(A) Carboxyl (B) Carbonyl (C) Ether (D) Alcohol

66.

Identify the functional group of one of the intermediates formed in wolff Kishner reduction
(A) Oxime (B) Hydrozone (C) Schiff's base (D) Enamine

67. CH3 – C º N A

CH3 – N C B
The relation between A and B
(A) Functional Isomers (B) Homologous
(C) Positional Isomers (D) None of the above

68. Identify the functional group

(A) Enamine (B) Hydrozide (C) Hydrozone (D) Imine

[11]
69.

Product P is

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

70.

The products A and B are respectively

(A) , CH3 – COOH (B) CH3 – COOH , CH4

(C) , (D) ,

71.

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

72. Major product is :

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

73. + CO2

x = number of b-ketoacids which could undergo the above reaction (include stereo isomerism).
The value of x is
(A) 1 (B) 2 (C) 3 (D) 4

[12]
74.

The products A, B and C respectively are

(A) , , (B) , ,

(C) , , (D) , ,

75. In which of the following reaction diastereomer will form ?

LiAlH
4® LiAlH
4®
(A) ¾¾ ¾¾ (B) ¾¾¾¾

LiAlH
4® LiAlH
(C) ¾¾¾¾ (D) 4®
¾¾¾¾

76.

Product(s) C is/are

(A) (B) (C) (D) All the above

Comprehansion : (Q.77 to Q.79) :

Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in
which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule
of alcohol gives an acetal and a molecule of water. We study this reaction

Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of
each reaction is given in the problem.

H+ H+
(A) ¾¾
¾® (P) (B) ¾¾
¾® (R)

H+
(C) + ¾¾
¾® (Q)

[13]
77. Product P is.

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

78. Product Q is.

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

79. Product R is.

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

Comprehansion : (Q.80 to Q.81) :

Carbonyl group show characteristic reaction of nucleophilic addition in which nucleophile attack is rate
determing step on carbonyl carbon.
80. Which pH is suitable for oxime formation
(A) 4 – 5 (B) 1 – 2 (C) 8 – 10 (D) 12 – 14
81. Which of the reactant show geometrical isomerism when it react with hydrazine (NH2 – NH2)

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

82. Match the following :

Column I Column II

(A) (P) An enamine will form

(B) (Q) Schiff base will form

(C) (R) Hydrazone will form

(D) (S) Product form will undergo Lassigne test

[14]
 EXERCISE-II
1. In a compound C, H and N atoms are present in 9 : 1 : 3.5 by weight. Molecular weight of compound is 108.
Molecular formula of compound is [AIEEE-2002]

(A) C2H6N2 (B) C3H4N (C) C6H8N2 (D) C9H12N3

2. When CH2 = CH – COOH is reduced with LiAlH4, the compound obtained will be [AIEEE-2003]

(A) CH3 – CH2 – COOH (B) CH2 = CH – CH2OH

(C) CH3 – CH2 – CH2OH (D) CH3 – CH2 – CHO

3. Which one the following does not have sp2 hybridized carbon? [AIEEE-2004]
(A) Acetone (B) Acetamide (C) Acetonitrile (D) Acetic acid

4. Which one of the following reduced with zinc and hydrochloric acid to give the corresponding hydrocarbon?
(A) Ethyl acetate (B) Butan -2-one (C) Acetamide (D) Acetic acid [AIEEE-2004]

5. Which of the following undergoes reaction with 50% sodium hydroxide solution to give the corresponding
alcohol and acid ? [AIEEE-2004]
(A) Phenol (B) Benzoic acid (C) Butanal (D) Benzaldehyde

6. Reaction of cyclohexanone with dimethylamine in the presence of catalytic amount of an acid forms a
compound if water during the reaction is continuously removed. The compound formed is generally known as
(A) a Schiff’s base (B) an enamine (C) an imine (D) an amine [AIEEE-2005]

7. Among the following the one that gives positive iodoform test upon reaction with I2 and NaOH is
[AIEEE-2006]

(A) CH3CH2CH(OH)CH2CH3 (B) C6H5CH2CH2OH (C) 3 (D) PhCHOHCH3

8. The increasing order of the rate of HCN addition to compounds A – D is [AIEEE-2006]

(I) HCHO (II) CH3COCH3 (III) PhCOCH3 (IV) PhCOPh
(A) I > II > III > IV (B) II > I > III > IV (C) III > IV > I > II (D) IV < III < II < I

Q
: OH ..
9. In Cannizzaro reaction given below , 2 Ph CHO ¾¾ ¾ ¾® Ph CH2OH + Ph COQ 2 the slowest step is :

(A) the abstraction of proton from the carboxylic group [AIEEE-2009]

(B) the deprotonation of Ph CH2OH

Q
(C) the attack of : OH at the carboxyl group
(D) the transfer of hydride to the carbonyl group

10. Trichloroacetaldehyde was subjected to Cannizzaro's reaction by using NaOH. The mixture of the products
contains sodium trichloroacetate ion and another compound. The other compound is : [AIEEE-2011]
(A) 2,2,2-Trichloroethanol (B) Trichloromethanol
(C) 2,2,2-Trichloropropanol (D) Chloroform

11. Sodium ethoxide has reacted with ethanoyl chloride. The compound that is produced in the above reaction is:
[AIEEE-2011]
(A) Diethyl ether (B) 2-Butanone (C) Ethyl chloride (D) Ethyl ethanoate

[15]
12. Silver Mirror test is given by which one of the following compounds ? [AIEEE-2011]
(A) Acetaldehyde (B) Acetone (C) Formaldehyde (D) Benzophenone
13. Iodoform can be prepared from all except : [AIEEE-2012]
(A) Ethyl methyl ketone (B) Isopropyl alcohol

(C) 3-Methyl-2-butanone (D) Isobutyl alcohol

14. Which of the following compounds can undergoes haloform reaction?

(A) (B) (C) (D) CH3 – CH2 – CHO

15. In the given transformation, which the following is the most appropriate reagent ? [AIEEE-2012]

Re agent
¾¾ ¾¾
¾®

(A) (B) Zn–Hg/HCl (C) Na, Liq, NH3 (D) NaBH4

16. A gaseous hydrocarbon gives upon combustion 0.72 g of water and 3.08 g of CO2. The empirical formula of
the hydrocarbon is : [JEE Main 2013]
(A) C7H8 (B) C2H4 (C) C3H4 (D) C6H5

17. Compound (A), C8H9Br, gives a white precipitate when warmed with alcoholic AgNO3. Oxidation of (A) gives
an acid (B), C8H6O4. (B) easily forms anhydride on heating. Identify the compound (A). [JEE Main 2013]
2
CH
(A) (B) (C) (D)
Br

18. Which of the following compounds is not expected to show Lassaignes’ test for nitrogen ?
(A) Hydroxylamine hydrochloride (B) Ethanamine [IIT JEE Main 2013]
(C) Propanenitrile (D) Nitromethane

19. Formaldehyde can be distinguished from acetaldehyde by the use of : [IIT JEE Main 2013]
(A) I2/Alkali (B) Schiff’s reagent (C) Fehling’s solution (D) Tollen’s reagent

20. For which of the following compounds Kjeldahl method can be used to determine the percentage of *
Nitrogen ? [IIT JEE Main 2013]
(A) Nitrobenzene (B) Alanine (C) Pyridine (D) Diazomethane

21. Which of the following is the product of aldol condensation ? [IIT JEE Main 2013]

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

[16]
22. 6 litres of an alkene require 27 litres of oxygen at constant temperature and pressure for complete
combustion. The alkene is : [IIT JEE Main 2013]
(A) 2-Butene (B) Propene (C) 1 - Butene (D) Ethene

23. Cannizaro’s reaction is not given by : [JEE Main 2013]

(A) (B) (C) HCHO (D) CH3CHO

24. Clemmensen reduction of a ketone is carried out in the presence of : [JEE Main 2013]
(A) Glycol with KOH (B) Zn - Hg with HCl (C) LiAlH4 (D) H2 with Pt as catalyst

25. Which of the following reagent (s) used for the conversion ? [JEE Main 2013]

¾¾®

(A) glycol/NaH/H3O+ (B) LiAlH4 (C) NaBH4 (D) glycol/LiAlH4/H3O+

26. Which is the major product formed when acetone is heated with iodine and potassium hydroxide ?
[JEE Main 2013]
(A) Iodoacetone (B) Acetic acid (C) Iodoform (D) Acetophenone

27. Chlorobenzene reacts with trichloro acetaldehyde in the presence of H2SO4

[JEE Main 2014]

The major product formed is :

(A) (B)

(C) (D)

28. Tischenko reaction is a modification of : [JEE Main 2014]

(A) Aldol condensation (B) Claisen condensation
(C) Cannizzaro reaction (D) Pinacol-pinacolon reaction

29. A compound A with molecular formula C10H13Cl gives a white precipitate on adding silver nitrate solution. A on
reacting with alcoholic KOH gives compound B as the main product. B on ozonolysis gives C and D. C gives
Cannizaro reaction but not aldol and D gives aldol but not Cannizaro reaction. A is :
[JEE Main 2015]
3
(A) 6 5 2 (B)
3

(C) C6H5–CH2–CH2–CH2–CH2–Cl (D)

[17]
30. In the reaction sequence [JEE Mains 2015]
-
OH D
2CH3 CHO ¾¾¾ ® A ¾¾ ® B; the product B is

(A) (B) CH3–CH2–CH2–CH2–OH (C) CH3–CH2–CH2–CH3 (D) CH3–CH=CH–CHO

31. Which compound would give 5-keto-2-methyl hexanal upon ozonolysis? [JEE MAIN 2015]

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

32. Which of the following pairs of compounds are positional isomers ? [JEE MAIN 2015]

(A)

(B)

(C)

(D)

33. The correct sequence of reagents for the following conversion will be [JEE-Main 2017]

(A) [Ag(NH3)2]+ OH–, CH3MgBr, H+ / CH3OH (B) [Ag(NH3)2]+ OH–, H+ / CH3OH, CH3MgBr
(C) CH3MgBr, H+ / CH3OH, [Ag(NH3)2]+OH– (D) CH3MgBr, [Ag(NH3)2]+ OH–, H+ / CH3OH
34. The major product formed in the following reaction is : [JEE-Main 2018]

(A) (B)

(C) (D)

[18]
35. The main reduction product of the following compound with NaBH4 in methanol is : [JEE-Main 2018]

(A) (B)

(C) (D)

36. The reagent(s) required for the following conversion are : [JEE-Main 2018]

(A) (i) B2H6 (ii) SnCl2/HCl (iii) H3O+ (B) (i) LiAlH4 (ii) H3O+
+
(C) (i) B2H6 (ii) DIBAl-H (iii) H3O (D) (i) NaBH4 (ii) Raney Ni/H2 (iii) H3O+
37. The major product of the following reaction : [JEE Main Online 2019]

(A) (B)

(C) (D)

38. The major product obtained in the following reaction is : [JEE Main Online 2019]

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

[19]
39. In the following reaction : [JEE Main Online 2019]

ˆˆˆˆ
HCl
carbonyl compound + MeOH ‡ˆˆˆ †
ˆ acetal
Rate of the reaction is the highest for :
(A) Propanal as substrate and methanol in excess
(B) Acetone as substrate and methanol in stoichiometric amount
(C) Acetone as substrate and methanol in excess
(D) Propanal as substrate and methanol in stoichiometric amount
40. Major products of the following reaction are : [JEE Main Online 2019]

(A) CH3OH and (B) HCOOH and

(C) CH3OH and HCO2H (D) and

41. The major product ‘Y’ in the following reaction is : [JEE Main Online 2019]

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

42. Compound A(C9H10O) shows positive iodoform test. Oxidation of A with KMnO4/KOH gives acid B(C8H6O4).
Anhydride of B is used for the preparation of phenolphthalein. Compound A is : [JEE Main Online 2019]

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

43. The major product (s) obtained in the following reaction is /are : [JEE Main Online 2019]

(A) (B)

(C) (D)

[20]
44. The most suitable reagent for the given conversion is : [JEE Main Online 2020]

(A) B2H6 (B) LiAIH4 (C) NaBH4 (D) H2/ Pd

45. Identify (A) in the following reaction sequence : [JEE Main Online 2020]

3
(B)
2 3

2 4

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

3

46. In the following reaction A is [JEE Main Online 2020]

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

47. [P] on treatment with Br2FeBr3 in CCl4 produced a single isomer C8H7O2 Br while heating [P] with sodalime
gave toluene. The compound [P] is : [JEE Main Online 2020]

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

[21]
48. In the following reaction sequence the major products A and B are : [JEE Main Online 2020]

(A) A = (B) A =

(C) A = (D) A =

49. The major products of the following reaction are : [JEE Main Online 2020]

i KO tBu/ D
¾¾¾¾¾
ii O /H O
®
3 2 2

(A) (B)

(C) (D)

50. Consider the following reactions : [JEE Main Online 2020]

ozonolysis
¾¾¾¾¾ ® ’B’ + ‘C’

‘A’ is :

(A) (B)

(C) (D)

[22]
51. The major product |C] of the following reaction sequence will be : [JEE Main Online 2020]

(A) (B)

(C) (D)

52. The compound A in the following reactions is : [JEE Main Online 2020]

3 2
A
2 4

(A) (B)

(C) (D)

53. An organic compound ‘A’ (C9H10O) when treated with conc. HI undergous cleavage to yield compounds ‘B’
and ‘C’. ‘B’ gives yellow precipitate with AgNO3 where as ‘C’ tautomerizes to ‘D’. ‘D’ gives positive iodoform
test. ‘A’ could be : [JEE Main Online 2020]

(A) (B)

(C) (D)

54. The increasing order of the following compounds towards HCN addition is :
[JEE Main Online 2020]

(i) (ii) (iii) (iv)

(A) (iii) < (i) < (iv) < (ii) (B) (iii) < (iv) < (ii) < (i) (C) (iii) < (iv) < (i) < (ii) (D) (i) < (iii) < (iv) < (ii)

[23]
55. The major aromatic product C in the following reaction sequence will be : [JEE Main Online 2020]

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

56. Match List -I and List -II [JEE Main Online 2021]
List -I List-II

(a) (i) Br2 / NaOH

(b) (ii) H2/Pd-BaSO4

(c) (iii) Zn(Hg)/ Conc. HCl

(d) (iv) Cl2 / Red P, H2O

3 2 3

Choose the correct answer the options given below :

(A) (a)-(ii), (b)-(iv), (c)-(i), (d)-(iii) (B) (a)-(ii), (b)-(i), (c)-(iv), (d)-(iii)
(C) (a)-(iii), (b)-(iv), (c)-(i), (d)-(ii) (D) (a)-(iii), (b)-(i), (c)-(iv), (d)-(ii)

57. Which of the following compound gives pink colour on reaction with phthalic anhydride in conc. H2SO4
followed by treatment with NaOH ? [JEE Main Online 2021]

(A) (B)

(C) (D)

58. 2,4-DNP test can be used to identify : [JEE Main Online 2021]
(A) Ether (B) Halogens (C) Aldehyde (D) Amine

59. Identify A in the given chemical reaction. [JEE Main Online 2021]

A (Major product)

(A) (B)

[24]
 (C) (D)

60. Identify A in the following chemical reaction. [JEE Main Online 2021]

(A) (B)

(C) (D)

61. [JEE Main Online 2021]

O

Which of the following reagent is suitable for thee preparation of the product in the above reaction ?

(A) NaBH4 (B) (C) Red P + Cl2 (D) Ni / H2

62. The major product of the following chemical reaction is : [JEE Main Online 2021]

(A) CH3CH2CH2OH (B) (CH3CH2CO)2O (C) CH3CH2CHO (D) CH3CH2CH3

63. Which one of the following reactions will not form acetaldehyde ? [JEE Main Online 2021]

Cu i DIBAL -H
(A) CH3CH2OH ¾¾¾®
573K (B) CH3CN ¾¾¾¾¾
ii H2O
®

CrO 3 -H2SO 4 Pd II /Cu II

(C) CH3CH2OH ¾¾¾¾¾¾ ® (D) CH = CH2 + O2 ¾¾¾¾¾®
HO 2

64. The major product of the following reaction is [JEE Main Online 2021]

H2 CO
CH3CH2CH = CH2 ¾¾¾ ®
Rh catalyst

(A) CH3 CH2C = CH2 (B) CH3CH2CH2CHO

|
CHO
(C) CH3CH2CH = CH — CHO (D) CH3CH2CH2CH2CHO

[25]
 A B
Hydrolysis
65. (C4H8 Cl2 ) ¾¾¾¾®
373 K
(C4H8 O) [JEE Main Online 2021]
B reacts with hydroxyl amine but does not give Tollen’s test. Identify A and B.
(A) 1, 1-Dichlorobutane and 2-Butanone (B) 1,1-Dichlorobutane and Butanal
(C) 2,2-Dichlorobutane and Butanal (D) 2,2-Dichlorobutane and Butan-2-one

O O
A
66. Major Product [JEE Main Online 2021]
OC 2H5
The product “A” in the above reaction is :
OH

O
O O
O O
(A) OH (B)
OC 2H5
OC 2H5

O
O
OC 2H5 O O
(C) (D)
OH OH

67.

The product “P” in the above reaction is : [JEE Main Online 2021]

(A) (B)

(C) (D)

68. An unsaturated hydrocarbon X on ozonolysis gives A. compound A when warmed with ammonical silver
nitrate froms a bright silver mirror along the sides of the test tube. The unsaturated hydrocarbon X is :
[JEE Main Online 2021]

CH3
(A) H3C C C CH3 (B) H3C C
CH3 CH3

(C) HC C CH2 CH3 (D) H3C C C CH3

[26]
69. 2

Consider the above reaction, the product 'X' and 'Y' respectively are : [JEE Main Online 2021]

(A) (B)

(C) (D)

[27]
 JEE ADVANCE
EXERCISE-I

1. Which one of the following is mixed ketone (Aliphatic & aromatic) :

O
||
(A) (B) (C) (D) CH3 - C 6H4 - C - CH2Ph

2. Two isomeric ketones, 3-pentanone and 2-pentanone can be distinguished by :

(A) I2 / NaOH (B) NaSO3H (C) NaCN / HCl (D) 2,4-DNP

3. Which of following give positive test with 2, 4-DNP ?

(A) (B) (C) (D) CH3 – CH2 – OH

4. Fehling solution gives red precipitate with:

(A) Aromatic aldehyde (B) Aliphatic aldehyde (C) Ketones (D) a -hydroxy ketones
5. Silver mirror test with Tollens reagent is given by :
(A) C6H5CHO (B) Ph–CH2–CHO
(C) C6 H5 - CH 2 - C - CH 2OH (D) CH3CHO
||
O
6. Which one of the following compounds will not give aldol:
(A) Acetaldehyde (B) Formaldehyde (C) Pivaldehyde (D) Crotonaldehyde
7. Schiff's reagent gives pink colour with :
(A) Acetaldehyde (B) Ph – CH3 (C) Acetic acid (D) Methyl acetate
8. Which of the following compound will give positive Tollens test

(A) CH3CHO (B)

(C) CH 3CH 2CH 2 CH 2CH - OCH 3 (D)

|
OH
9. Mixture of Ph–CHO & HCHO is treated with NaOH then Cannizzaro reaction involves:
(A) Oxidation of HCHO (B) Reduction of HCHO
(C) Oxidation of Ph–CHO (D) Reduction of Ph–CHO

Conc. KOH
10. PhCHO + HCHO ¾¾¾ ¾¾®
Correct statement regarding reaction will be
(A) It is an example of redox reaction (B) HCHO is oxidised
(C) It is cross Cannizaro reaction (D) Ph–CHO is reduced

[28]
 EXERCISE-II
Single Choice Questions :
1. The reagent with which both acetaldehyde and acetone react easily is [IIT 1982]
(A) Tollen reagent (B) Schiff reagent (C) Grignard reagent (D) Fehling reagent

2. The Cannizzaro reaction is not given by

(A) trimethyl acetaldehyde (B) acetaldehyde [IIT 1983]
(C) benzaldehyde (D) formaldehyde
3. When acetaldehyde is heated with Fehling solution, it gives a precipitate of [IIT 1983]
(A) Cu (B) CuO (C) Cu2O (D) Cu + Cu2O + CuO
4. m-chlorobenzaldehyde on reaction with conc. KOH at room temperature gives: [IIT 1991]
(A) Potassium m-chlorobenzoate and m-hydroxybenzaldehyde
(B) m-hydroxybenzaldehyde and m-chlorobenzyl alcohol
(C) m-chlorobenzyl and m-hydroxybenzyl alcohol
(D) Potassium m-chlorobenzoate and m-chlorobenzyl alcohol
5. Hydrogenation of benzoyl chloride in the presence of Pd and BaSO4 gives: [IIT 1992]
(A) Benzyl alcohol (B) Benzaldehyde (C) Benzoic acid (D) Phenol

6. Under Wolff Kishner reduction conditions, the conversions which may be brought about is? [IIT 1995]
(A) Benzaldehyde into Benzyl alcohol (B) Cyclohexanol into Cyclohexane
(C) Cyclohexanone into Cyclohexanol (D) Benzophenone into Diphenylmethane
7. In the reaction, P is [IIT 1995]

SeO
2
CO ¾¾¾ ® P + Se + H2O

(A) CH3COCHO (B) CH3COOCH3 (C) CH3COCH2OH (D) None

8. OH-
In the Cannizzaro reaction given below, 2Ph–CHO ¾¾¾® Ph–CH2OH + PhCO -2 the slowest step is :
(A) the attack of OH– at the carbonyl group
(B) the transfer of hydride to the carbonyl group
(C) the abstraction of proton from the carboxylic acid
(D) the deprotonation of Ph–CH2OH [IIT 1996]
9. In a Cannizzaro reaction the intermediate which is the best hydride donor is: [IIT 1997]

H H
| |
- -
(A) C 6 H 5 - C - O (B) C 6 H 5 - C - O (C) (D)
| |
OH O-
10. A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution gives: [IIT 2001]
(A) benzyl alcohol and sodium formate (B) sodium benzoate and methyl alcohol
(C) sodium benzoate and sodium formate (D) benzyl alcohol and methyl alcohol
11. 1-propanol & 2-propanol can be best distinguished by: [IIT 2001]
(A) Oxidation with alkaline KMnO4 followed by reaction with Fehling solution
(B) Oxidation with acedic dichromate followed by reaction with Fehling solution
(C) Oxidation by heating with copper followed by reaction with Fehling solution
(D) Oxidation with concentrated H2SO4 followed by reaction with Fehling

[29]
12.
¾(¾
i ) NaOH ( excess)100° C
¾ ¾ ¾ ¾ ¾¾® [IIT 2003]
(ii ) H + / H 2O

any one of the products formed is :

(A) (B)

(C) (D)

CH COONa
13. + X ¾¾3¾ ¾¾® [IIT 2005]

What is X?
(A) CH3COOH (B) BrCH2, COOH (C) (CH3CO)2O (D) CHO–COOH

14. How will you convert butane-2-one to propanoic acid? [IIT 2005]
(A) Tollen reagent (B) Fehling solution (C) NaOH / I2 / H+ (D) NaOH / NaI /H+

15. Which of the following reactants on reaction with conc. NaOH followed by acidification gives the following
lactone as the only product? [IIT 2006]

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

16. Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E. Compound E
on further treatment with aqueous KOH yields compound F. Compound F is [IIT 2007]

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

17. Statement-1 : Glucose gives a reddish-brown precipitate with Fehling’s solution. [IIT 2007]
because
Statement-2 : Reaction of glucose with Fehling’s solution gives CuO and gluconic acid.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.

[30]
18. The number of aldol reaction (s) that occurs in the given transformation is : [IIT 2012]

conc . aq. NaOH

CH3CHO + 4HCHO ¾¾ ¾ ¾ ¾¾®

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

19. The major product H in the given reaction sequence is [IIT 2012]
Q
CN
95% H2SO 4
CH3 – CH2 – CO – CH3 ¾¾¾® G ¾¾¾ ¾ ¾® H
Heat

(A) (B)

(C) (D)

20. The major product of the following reaction is [JEE ADVANCE 2015]

3 3

(A) (B) (C) 3 (D)

21. In the following reactions, the product S is [JEE ADVANCE 2015]

(A) (B)

(C) (D)

[31]
22. The correct order of acidity for the following compounds is : [JEE ADVANCE 2016]

(A) I > II > III > IV (B) III > I > II > IV (C) III > IV > II > I (D) I > III > IV > II
23. The major product of the following reaction sequence is : [JEE ADVANCE 2016]

(A) (B)

(C) (D)

Mathcing List Type :

24. Different possible thermal decomposition pathways for peroxyesters are shown below. Match each pathway
from List-I with an appropriate structure from List - II and select the correct answer using the code given
below the lists. [JEE Advance 2014]

­
List - I List - II

(P) Pathway P 1.

(Q) Pathway Q 2.

(R) Pathway R 3.

(S) Pathway S 4.

[32]
 Codes :
P Q R S
(A) 1 3 4 2
(B) 2 4 3 1
(C) 4 1 2 3
(D) 3 2 1 4

Paragraph for Question No. 25 to 27 [IIT 2008]

A tertiary alcohol H upon acid catalysed dehydration gives a product I. Ozonolysis of I leads to compounds
J and K. Compound J upon reaction with KOH gives benzyl alcohol and a compound L, whereas K on
reaction with KOH gives only M.

M=

25. Compound H is formed by the reaction of

(A) + PhMgBr (B) + PhCH2MgBr

(C) + PhCH2MgBr (D) +

26. The structure of compound I is

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

27. The structures of compounds J, K and L, respectively, are

(A) PhCOCH3, PhCH2COCH3 and PhCH2COO¯K+ (B) PhCHO, PhCH2CHO and PhCOO¯K+
(C) PhCOCH3, PhCH2CHO and CH3COO¯K+ (D) PhCHO, PhCOCH3 and PhCOO¯K+

Paragraph for Question Nos. 28 to 30 [IIT 2009]

A carbonyl compound P, which gives positive iodoform test, undergoes reaction with MeMgBr followed by
dehydration to give an olefin Q. Ozonolysis of Q leads to a dicarbonyl compound R, which undergoes
intramolecular aldol reaction to give predominantly S.

1. MeMgBr 3® 1. O 1. OH–
P ¾¾ ¾ ¾ ¾® Q ¾¾ ¾
¾ R ¾¾ ¾¾® S
2. H+ ,H2O 2. Zn, H2O 2. D
3.H2SO 4 ,D
28. The structure of the carbonyl compound P is

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

O Me

[33]
29. The structures of the products Q and R, respectively, are

(A) , (B) ,

(C) , (D) ,

30. The structure of the product S is :

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

Paragraph for Question Nos. 31 and 32

An acyclic hydrocarbon P, having molecular formula C6H10, gave acetone as the only organic product through
the following sequence of reaction, in which Q is an intermediate organic compound. [IIT 2011]

31. The structure of compound P is :

(A) CH3CH2CH2CH2 – C º C – H (B) H3CCH2 – C º C – CH2CH3

(C) (D)

32. The structure of the compound Q is :

(A) (B)

(C) (D)

[34]
Paragraph for Questions Nos. 33 to 34 [IIT 2012]
In the following reactions sequence, the compound J is an intermediate,

(CH3 CO)2 O (i) H2 ,Pd / C

I J ¾¾¾ ¾¾® K
CH3 COONa (ii ) SOCl 2
(iii) anhyd. AlCl 3

J (C9H8O2) gives effervescence on treatment with NaHCO3 and positive Baeyer's test
33. The compound K is

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

34. The compound I is

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

Paragraph for Question Nos. 35 and 36 [IIT-JEE Advanced 2018]

Treatment of benzene with CO/HCl in the presence of anhydrous AlCl3/CuCl followed by reaction with
Ac2O/NaOAc gives compound X as the major product. Compound X upon reaction with Br2/Na2CO3, followed
by heating at 473 K with moist KOH furnishes Y as the major product. Reaction of X with H2/Pd-C, followed
by H3PO4 treatment gives Z as the major product.
(There are two questions based on Paragraph "X", the question given below is one of them)
35. The compound Y is

(A) (B)

(C) (D)

36. The compound Z is

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

Paragraph for Question Nos. 37 and 38 [IIT-JEE Advanced 2018]

An organic acid P (C1H12O2) can easily be oxidized to a dibasic acid which reacts with ethyleneglycol to
produce a polymer dacron. Upon ozonolysis, P gives an aliphatic ketone as one of the products. P undergoes
the following reaction sequences to furnish R via Q. The compound P also undergoes another set of reactions
to produce S.

[35]
 2
2
3
2 2
2

2 2
+
2 4 3

(There are two questions based on PARAGRAPH "A", the question given below is one of them)
37. The compound R is

(A) (B)

(C) (D)

38. The compound S is

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

One or more than one correct type :

39. Which of the following compounds will give a yellow precipitate with iodine and alkali ? [IIT 1984]
(A) 2-hydroxy propane (B) Acetophenone (C) Methyl acetate (D) Acetamide

40. Among P, Q, R and S, the aromatic compound(s) is/are [IIT-JEE Advanced 2013]

AlCl
3
¾¾¾ ® P

NaH
¾¾¾® Q

(NH4 )2 CO3
¾¾ ¾ ¾¾® R
100 –115 °C

HCl
¾¾¾® S

(A) P (B) Q (C) R (D) S

[36]
41. Positive Tollen’s test is observed for [JEE ADVANCED 2016]

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

42. Compounds P and R upon ozonlysis produce Q and S, respectively. The molecular formula of Q and S is
C8H8O. Q undergoes Cannizzaro reaction but not haloform reaction, whereas S undergoes haloform reaction
but not Cannizzaro reaction. [JEE ADVANCED 2017]

(i)

(ii)

The option(s) with suitable combination of P and R, respectively, is(are)

(A) and (B) and

(C) and (D) 3 and 3

43. The reaction(s) leading to the formation of 1,3,5-trimethylbenzene is(are) [JEE ADVANCED 2018]

(A) (B)

(C) (D)

Match the column :

44. Match the compounds/ion in column I with their properties/ reaction in Column II. Indicate your answer by
darkening the appropriate bubbles of the 4 × 4 matrix given in the ORS. [IIT 2007]
Column I Column II
(A) C6H5CHO (P) gives precipitate with 2,4-dinitrophenylhydrazine
(B) CH3CºCH (Q) gives precipitate with AgNO3
(C) CN– (R) is a nucleophile
(D) I– (S) is involved in cyanohydrin formation

[37]
45. Match the compounds in Column I with their characteristic test(s)/reaction(s) given in Column II. Indicate
your answer by darkening the appropriate bubbles of the 4 × 4 matrix given in the ORS.
Column I Column II [IIT 2008]

(A) H2N – (P) sodium fusion extract of the compound gives

Prussian blue colour with FeSO4

(B) (Q) gives positive FeCl3 test

(C) (R) gives white precipitate with AgNO3

(D) (S) reacts with aldehydes to form the corresponding

hydrazone derivative

Subjective :
46. The total number of carboxylic acid groups in the product P is [JEE ADVANCE : 2013]

(P)

47. In the following reaction sequence, the amount of D(in g) formed from 10 moles of acetophenone is_______.
(Atomic weights in g mol–1 : H = 1, C = 12, N = 14, O = 16, Br = 80. The yield (%) corresponding to the
product in each step is given in the parenthesis) [JEE ADVANCE : 2018]

[38]
 EXERCISE-III
1. The formation of cyanohydrin from a ketone is an example of: [IIT 1990]
(A) Electrophilic addition (B) Nucleophilic addition
(C) Nucleophilic substitution (D) Electrophilic substitution

2. An organic compound C3H6O does not give a precipitate with 2,4-Dinitrophenyl hydrazine reagent and does
not react with metallic sodium. It could be: [IIT 1993]
(A) CH3CH2CHO (B) CH3COCH3
(C) CH2=CH–CH2OH (D) CH2=CH–O–CH3

3. Which of the following carboxylic acids undergoes decarboxylation easily ? [IIT 1995]
(A) C6H5COCH2COOH (B) C6H5COCOOH
(C) C6H5CH(OH)COOH (D) C6H5CH(NH2)COOH

4. Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is
(A) MeCOCl (B) MeCHO
(C) MeCOOMe (D) MeCOOCOMe [IIT 1996]

5. CH3CHO + H2NOH ¾® CH3 – CH = N – OH. The above reaction occurs at: [IIT 1997]
(A) pH = 1 (B) pH = 4.5
(C) Any value of pH (D) pH = 12

6. Among the following compounds, which will react with acetone to give a product containing [IIT 1998]

(A) C6H5NH2 (B) (CH3)3N

(C) C6H5NHC6H5 (D) C6H5NHNH2

7. Compound A (molecular formula C3H8O) is treated with acidified potassium dichromate to form a product B
(molecular formula C3H6O). B forms a shining silver mirror on warming with ammonical silver nitrate. B when
treated with an aqueous solution of H2NCONHNH2. HCl and sodium acetate gives a product C. Identify the
structure of C.

(A) CH3CH2CH = NNHCONH2 (B) CH 3 - C = NNHCONH2 [IIT 2002]

|
CH 3

(C) CH 3 - C = NCONHNH2 (D) CH3CH2CH=NCONHNH2

|
CH 3

8. The smallest ketone and its next homologue are reacted with NH2OH to form oxime. [IIT 2006]
(A) Two different oximes are formed (B) Three different oximes are formed
(C) Two oximes are optically active (D) All oximes are optically active

9. The compound that undergoes decarboxylation most readily under mild condition is [IIT 2012]

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

[39]
10. Acetophenone on reaction with hydroxylamine-hydrochloride can produce two isomeric oximes. Write
structures of the oximes. [IIT 1997]

11. Five isomeric para-disubstituted aromatic compounds A to E with molecular formula C8H8O2 were given for
identification. Based on the following observations, give structure of the compounds.
(i) Both A and B form a silver mirror with Tollen's reagent; also, B gives a positive test with FeCl3 solution
(ii) C gives positive iodoform test.
(iii) D is readily extracted in aqueous NaHCO3 solution.
(iv) E on acid hydrolysis gives 1,4-dihydroxybenzene. [IIT 2002]

12. C6H12 ¾HCl

¾¾® C6H13Cl + (C)

(A) (B)

(D) ¾ozonolysis
¾ ¾¾® (E)

ozonolysis NaOH
(A) ¾¾¾¾
¾® (F) + (G) ¾¾ ¾
¾® HCOONa + 1° alcohol
(D) is isomer A. E gives negative test with Fehling solution but gives iodoform test. F and G gives Tollen's test
but do not give iodoform test. Identify A to G. [IIT 2003]

13. Give major products A, B, C and D in following reaction sequence. [IIT 2004]

Å
¾KCN
¾¾® (A) ¾(¾ ¾ ¾ ¾¾® (B) ¾H¾
i ) NaOEt / EtOH 3O
¾® (C) ¾
(i ) SOCl2
¾ ¾¾ ¾® (D)
DMF (ii ) CH – NH
(ii ) PhCHO / D 3 2

14. Which of the following disaccharide will not reduce Tollen's reagent? [IIT 2005]

(a) (b)

(Q) (P)

+
H ,D (i) O 3 aq. KOH
15. ¾¾ ¾® X ¾¾ ¾ ¾ ¾¾® Y.. ¾¾ ¾¾® ( Z) [IIT 2005]
D
( ii) Zn / CH3COOH major product

Identify X, Y and Z.

16. In the scheme given below, the total number of intramolecular aldol condensation products formed from ‘Y’ is

1. O1. NaOH( aq )
3 ® Y ¾¾
¾¾ ¾
¾ ¾ ¾ ¾® [IIT 2010]
2. Zn, H2O 2. heat

[40]
17. Choose the correct option(s) for the following set of reactions [IIT Adv. 2019]

(1) (2)

(3) (4)

Answer the following by appropriately matching the lists based on the information given in the paragraph
(Q.18 to Q.19) [IIT Adv. 2019]
List-I includes starting materials and reagents of selected chemical reactions. List -II gives structures of
compound that may be formed as intermediate products and/or final products form the reactions of List-I.

List-I List-II

(I) (P)

(II) (Q)

(III) (R)

(IV) (S)

(T)

(U)

[41]
18. Which of the following options has correct combination considering List-I and List-II ?
(1) (I), (Q), (T), (U) (2) (II), (P), (S), (U) (3) (II), (P), (S), (T) (4) (I), (S), (Q), (R)

19. Which of the following options has correct combination considering List-I and List-II ?
(1) (III), (S), (R) (2) (IV), (Q), (U) (3) (III), (T), (U) (4) (IV), (Q), (R)

20. Total number of hydroxyl groups present in a molecule of the major product P is ________. [IIT Adv. 2019]

21. Total number of isomers, considering both structural and stereoisomers, of cyclic ethers with the molecular
formula C4H8O is _______. [JEE Advanced 2019]

22. Choose the correct option(s) for the following reaction sequence : [JEE Advanced 2019]

Consider Q, R and S as major products

(1)

(2)

(3)

(4)

[42]
23. Consider the following transformations of a compound P. [JEE Advanced 2020]

Choose the correct option(s)

(A) P is (B) X is Pd-C / quinoline / H2

(C) P is (D) R is

24. In the reaction scheme shown below, Q, R, and S are the major products. [JEE Advanced 2020]

The correct structure of

CH3 CH3 CH3 CH3

H3C H3C H3C H3C

H3C H3C

(A) S is (B) Q is

CH3 HO2C O

CH3 CH3 CH3

H3C H3C CH3
H3C H3C
H3C H3C
H3C
(C) R is (D) S is

[43]
25. The correct order of acid strength of the following carboxylic acids is
[JEE Advanced 2019]

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

26. In the following reaction, compound Q is obtained from compound P via an ionic intermediate.
[JEE Advanced 2020]
CO 2CH3
H5 C6 C6 H5
conc.H2SO4
¾¾¾¾¾ ® Q (A colored compound)

C 6H 5
What is the degree of unsaturation of Q ?

Questions Stem for Questions Nos. 27 and 28

Question Stem
For the following reaction scheme, percentage yields are given along the arrow :

x g and y g are mass of R and U, respectively. [JEE Advanced 2021]

(Use : Molar mass (in g mol–1) of H, C and O as 1, 12 and 16, respectively)

27. The value of x is _________.

28. The value of y is :

29. In the reaction given below, the total number of atoms having sp2 hybridization in the major product P is ____.

3 1.O (excess)thenZn/H O
2
¾¾¾¾¾¾¾¾¾¾
2.NH OH(excess)
®P [JEE Advanced 2021]
2

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30. Considering the reaction sequence given below, the correct statement(s) is(are)

(A) P can be reduced to a primary alcohol using NaBH4.

(B) Treating P with conc. NH4OH solution followed by acidification gives Q.
(C) Treating Q with a solution of NaNO2 in aq. HCl liberates N2.
(D) P is more acidic than CH3CH2COOH. [JEE Advanced 2022]

31. The option(s) with correct sequence of reagents for the conversion of P to Q is(are)

(A) i) Lindlar’s catalyst, H2; ii) SnCl2 / HCl; iii) NaBH4; iv) H3O+ [JEE Advanced 2024]
+
(B) i) Lindlar’s catalyst, H2; ii) H3O ; iii) SnCl2 / HCl; iv) NaBH4
(C) i) NaBH4; ii) SnCl2 / HCl; iii) H3O+; iv) Lindlar’s catalyst, H2
(D) i) Lindlar’s catalyst, H2; ii) NaBH4; iii) SnCl2 / HCl; iv) H3O+

Paragraph (Q. 32 to Q. 33)

An organic compound P with molecular formula C9H18O2 decolorizes bromine water and also shows positive
iodoform test. P on ozonolysis followed by treatment with H2O2 gives Q and R. While compound Q shows
positive iodoform test, compound R does not give positive iodoform test. Q and R on oxidation with pyridinium
chlorochromate (PCC) followed by heating give S and T, respectively. Both S and T show positive iodoform
test.
Complete copolymerization of 500 moles of Q and 500 moles of R gives one mole of a single acyclic
copolymer U.
[Given, atomic mass : H = 1, C = 12, O = 16] [JEE Advanced 2024]

32. Sum of number of oxygen atoms in S and T is _____.

33. The molecular weight of U is _____.

34. Complete reaction of acctaldehyde with excess formaldehyde, upon heating with conc. NaOH solution,
gives P and Q. Compount P does not give Tollens’ test, whereas Q on acidification gives positive Tollens’
test. Treatement of P with excess cyclohexanone in the presence of catalytic amount of p-toluenesulfonic
acid (PTSA) gives product R.
Sum of the number of methylene groups (-CH2-) and oxygen atoms in R is ________.
[JEE Advanced 2024]

[45]
 ANSWER KEY
JEE MAINS
EXERCISE-I
1. B 2. C 3. D 4. B 5. D 6. D 7. B
8. C 9. D 10. C 11. B 12. C 13. C 14. B
15. C 16. B 17. D 18. C 19. D 20. A 21. B
22. B 23. B 24. D 25. C 26. B 27. A 28. D
29. B 30. C 31. A 32. B 33. A 34. D 35. A
36. B 37. B 38. B 39. C 40. B 41. C 42. D
43. A 44. C 45. D 46. C 47. C 48. B 49. D
50. C 51. D 52. C 53. D 54. C 55. B 56. B
57. C 58. B 59. D 60. D 61. C 62. B 63. B
64. C 65. B 66. B 67. A 68. A 69. B 70. A
71. B 72. A 73. C 74. B 75. A 76. AB 77. B
78. B 79. B 80. A 81. D 82. A – PS, B – QS, C – QS, D – RS

EXERCISE-II
1. C 2. B 3. C 4. B 5. D 6. B 7. D
8. A 9. D 10. A 11. D 12. AC 13. D 14. A
15. A 16. A 17. A 18. A 19. A 20. B 21. C
22. B 23. D 24. B 25. D 26. C 27. C 28. C
29. A 30. D 31. C 32. A 33. A 34. C 35. C
36. A 37. C 38. B 39. A 40. B 41. D 42. C
43. A 44. A 45. C 46. B 47. A 48. B 49. D
50. D 51. A 52. C 53. C 54. A 55. C 56. A
57. D 58. C 59. C 60. A 61. B 62. C 63. C
64. D 65. D 66. B 67. B 68. C 69. C

JEE ADVANCE
EXERCISE-I
1. CD 2. AB 3. AB 4. BD 5. ABCD

6. BC 7. A 8. ABC 9. AD 10. ABCD

EXERCISE-II
1. C 2. B 3. C 4. D 5. B 6. D 7. A
8. B 9. D 10. A 11. C 12. C 13. C 14. C
15. C 16. A 17. C 18. C 19. A 20. A 21. A
22. A 23. A 24. A 25. B 26. A 27. D 28. B
29. A 30. B 31. D 32. B 33. C 34. A 35. C
36 A 37. A 38. B 39. AB 40. ABCD 41. ABC 42. AC
43. ABD 44. A ® P, S ; B ® Q,R ; C ® Q, R, S ; D ® Q,R
45. A ® R, S ; B ® P, Q ; C ® P, Q, R ; D ® P,S OR A ® R ; B ® P, Q ; C ® P, Q, R ; D ® P
46. 2 47. 495

[46]
 EXERCISE-III
1. B 2. D 3. A 4. A 5. B 6. A 7. A
8. B 9. B

10.

11. (A) or (B) (C) (D) (E)

12. Me3C – CH=CH2 ¾HCl

¾¾® Me2 C –CHMe2 + Me3C– CH –Me
| |
Cl Cl
(A) (B) (C)

alc . KOH O
3 ®
Me2 C –CHMe2 ¾¾ ¾¾® ¾¾¾
D Zn, H2O
|
Cl
(A) ¾Ozonolysis
¾¾¾ ¾® HCHO + Me3C–CHO ¾NaOH
¾¾®
(F) (G)
HCOONa + Me3C–CH2OH (1°alcohol)

13. (A) (B) (C) (D)

14. In structure (P) both the rings are present in acetyl form therefore it will not hydrolyse in solution that why
Tollen's solution cannot react with this.
In structure (Q) one ring present in the form of hemiacetal. This will hydrolysed in solution it can reduce
Tollen's solution.

15. (X) , (Y) , (Z)

16. 1

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17. 2, 4
Sol. C6H10O
DU = 2

18. 2

19. 4
Sol.

(I)

(II)

(III)

(IV)

[48]
20. 6.00
Sol.

21. 10.00
Sol. C4H8O (Cyclic ether)

22. (1, 3)
Sol.

23. BC 24. BD 25. A 26. 18.00 to 18.00 27. 1.62 gm

28. 3.9 gm 29. 8.00 30. B,C,D 31. C,D 32. 2.00 33. 93018
34. 18.00

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