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Path to success KOTA (RAJASTHAN) WORKSHEET-21
Path to success KOTA (RAJASTHAN) CHEMISTRY
TOPIC : Alcohol, phenol and ether DT. 27/11/2023
1. Dihydric alcohol among the following compound are 4. Major product of the given reaction is
(i) m–cresol (ii) quinol
O
(iii) glycerol (iv) ethylene glycol CH 3 Mg Br H2 O
CH3 – C – C2H5 A B+C
(1) (i) and (ii) (Major)
(2) (ii) and (iv)
The major product B is
(3) (i), (ii) and (iv)
OH
(4) only (iii)
(1) CH3 – CH – C2H5
2. Which of the following are unsymmetrical ether
CH 3
(i) CH3OCH3 (ii) C2H5OC2H5
(2) CH3 – CH – CH2 – OH
CH3 CH3 OH
OC2H5 (3) CH3 – C – C2H5
(iii) C6H5OCH2CH3 (iv) CH3
OH
(4) CH3 – C – C2H5
(1) (i), (iii) and (iv) (2) (iii) and (iv)
C2H5
(3) (ii) and (iii) (4) (i) and (iv)
3. Which of the following compound has wrong O O
IUPAC name? NaBH 4
CH2 – C – O – CH3 A
5.
CH3 – CH – CH – CH – CH2OH
(1) Cl CH3 CH3
4–chloro–2, 3–dimethyl pentan–1–ol Product A is
OH
CH3 – CH – O – CH2 – CH3
CH2 – CH2 – OH
(2) CH3 (1)
2–ethoxy propane

O
OH
CH3 CH3 CH2 – CH2 – OH
(2)
(3)
OH
2, 6–dimethylphenol OH
CH2 – CH – CH3
(3)
NO2
OC2H5
OH O
(4)
CH2 – C – O – CH3
2–ethoxy–1–nitrocyclohexane (4)

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6. Which of the following compound has lowest 1 0 . Lucas reagent is equimolar solution of
boiling point (1) Conc. H2SO4 and conc. HNO3
(1) n-Butyl alcohol (2) isobutyl alcohol (2) Conc. HNO3 and anhydrous ZnCl 2
(3) tert–butyl alcohol (4) sec–butyl alcohol (3) Conc. HCl and anhydrous ZnCl2
7. Order of acidic nature of the following compound is (4) Conc. H2SO4 and anhydrous ZnCl2
OH OH 1 1 . In the reaction
NO2
(A) (B) – CH2 – O – HBr
the products are
NO2

OH
OH (1) – CH2 – OH + – Br

(C) (D)
(2) – CH2 – Br + – OH
CH3
CH3
(1) B > A > D > C (2) A > B > C > D
(3) – CH2 – Br + – Br
(3) A > C > B > D (4) B > C > D > A
COOH
OH (4) – CH2 – OH + – OH
+
H
8. + (CH3CO)2O A+B
OCH3
Product A and B are
OH 12. + Conc. HNO3+ Conc. H2SO4 A
OCOCH3
(1) + CH3COOH Major product A is

OCH3
COOH OCH3
OCOCH3
NO2
(2) + CH3COCH3 (1) (2)
NO2
COOH
OCOCH3 OCH3 OCH3
(3) + CH3COOH
(3) (4)
(4) None of the above NO2
9. The relative ease of dehydration of alcohol follows 13. The product of acid catalysed hydration of 2–
the order phenylpropene is
(1) Primary > Secondary > Tertrary (1) 3–phenyl–2–propanol
(2) Secondary > Tertrary > Primary (2) 1–phenyl–2–propanol
(3) Tertrary > Secondary > Primary (3) 2–phenyl–2–propanol
(4) Primary > Tertrary > Secondary
(4) 2–phenyl–1–propanol

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1 4 . Phenol is treated with Br2 in CS2 then major 1 7 . Nitration of phenol with conc. HNO3 gives?
product is OH OH
OH
OH NO2
Br (1) (2)
Br NO2
Br
(1) (2)
OH
Br OH
OH
OH NO2 NO2
(3) (4)

(3) (4) NO2 NO2

Br
1 8 . Which one is the wrong statement?
Br
(1) Phenol react with dil HNO3 yeilds a mixture
15. The reaction of CH3 – CH = CH – – OH of ortho & para nitrophenol
(2) Orthonitrophenol is steam volatile due to
with HBr gives intermoelcular H–bonding
(3) Phenol is converted to benzene on heating with
zinc dust
(1) CH3 – CH – CH 2 – – OH
(4) CH3OH also known as wood spirit
Br
19.  CH3 3 C  OC2 H5  HI  A  B . Identify A and B
(2) CH3 – CH 2 – CH – – OH CH3
Br (1) CH3 – C – OH and CH3CH2–I
CH3
(3) CH3 – CH – CH 2 – – Br
CH3
Br
(2) CH3 – C – OH and CH3CH2OH
CH3
(4) CH3 – CH2 – CH – – Br
Br CH3
+ (3) CH3 – C – I and CH3–CH2–I
OH O Na
CH3
CHCl3 + aq. NaOH CHCl2 NaOH
16.
CH3
(4) CH3 – C – I and CH3–CH2–OH
+
O Na OH CH3
CHO
H +
CHO
20. The correct order of boiling point is
CH 3(CH 2) 3CH3 C2H 5–O–C 2H 5
This reaction is associated with the name of I II
(1) Kolbe's reaction CH 3(CH 2) 3–OH
(2) Finkelstein reaction III
(3) Reimer–Tiemann reaction (1) I > II > III (2) II > I > III
(4) Swart reaction (3) III > II > I (4) III > I > II
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2 1 . Which one is the correct statement? 2 5 . Reaction by which carbonyl compound can not
(1) Williamson synthesis of ether is an important be prepared
laboratary method for the preparation of
(1) RCH 2 OH 
Cu

symmetrical and unsymmetrical ether 573K

(2) Mechanism of this reaction is SN2 Cu

R – CH – R'
(2) 573K
(3) Better result are obtained if the alkyl halide is OH
primary CH3
(4) All of these CrO3
(3) CH3 – C – OH
CH 3
H+/heat CH3
22. CH3 – CH – CH – CH3 [A]
OH Major Product (4) RCH 2 OH 
CrO3

Major product A is
2 6 . Arrange the following compound in decreasing
CH3 order of their acidic strength
(1) CH2 = C – CH 2 – CH3 4–Methylphenol 2,4,6–trinitrophenol
CH 3 I II
(2) CH3 – C = CH – CH3 3–Nitrophenol 3,5–dinitrophenol
CH3 III IV
(3) CH3 – CH – CH = CH2 (1) II > III > IV > I (2) I > II > IV > III
(4) None of the above (3) II > I > IV > III (4) II > IV > III > I
23. Which one of the following is incorrect? 27. Arrange the following compound in order of their
decreasing boiling point?
ZnOCr O
(1) CO  2H2 
   
2 3
200300 atm

CH3OH
pentan-1–ol butan–1–ol
573 673K
(2) C12 H 22 O11  H 2 O 
Zymase
 C6 H12 O 6  C 6 H12 O6 I II
butan–2–ol propan–1–ol
(3) C6 H12 O6 
Zymase
 C 2 H 5 OH  CO 2
III IV
(4) B.P. of ethanol is 351K (1) I > III > II > IV (2) II > I > III > IV
2 4 . Consider the following reaction (3) I > II > III > IV (4) I > IV > II > III
OH O
NaBH4
Na2Cr2O7
A 28. CH3 – CH2 – CH – C – H [A]
H2SO4
CH3
The product A is The product A is
OH (1) CH3 – CH2 – CH – CH3
CH3
(1) (2) (2) CH3 – CH2 – CH – CH2OH
OH CH3
O
O
C–H (3) CH3 – CH2 – CH – OH
CH3
(3) (4)
(4) CH3 – CH2 – CH2 – CH3
O

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CH3 3 2 . In the given reaction

CH3 – CH – CH3 CH3 – C – O – OH

29. O2 H+
x+y
H2O
Product (Major)
product x and y are
O
C – CH3 The product will be

(1) (1) Cis-2-butene

and CH3OH
(2) Trans-2-butene
(3) 2-butyne
OH
(4) Buta-1, 3-diene
(2) and CH3COCH3 3 3 . Maximum dehydration takes place in -
O O
O OH
(1) (2)
C–H
OH
(3) and CH3 – CH2 – OH O CH2

(4) None of the above (3) (4)

SO3H OH
OH
OH
P (i) NaOH
30. +
34. The major product in the following reaction is
(ii) H

H+
The reagent P is CH2 – OH ?

(1) SO3 (2) H2SO4
(3) Oleum (4) H2SO3
CH3
CH3 CH2
(1) (2)
[Link]
31. A OH
Cl
Cl CH3 CH3
(3) (4)
[Link]
B
Cl 35. Deoxygenation of phenol can be achieved by
Product A and B (major) are respectively : distillation with
CH3 CH3 (1) Raney nickel
(1) (2)
(2) Lithium aluminium hydride
CH3 CH3 (3) Sodium borohydride
(3) (4)
(4) Zinc dust

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36. Which of the following compounds shows 41. The reaction of ethyl iodide with sodium ethoxide is
intramolecular hydrogen bonding? (1) An electrophilic substitution reaction
(1) p-Nitrophenol (2) Ethanol (2) A nucleophilic addition reaction
(3) o-Nitrophenol (4) Methanamine (3) A nucleophilic substitution reaction
(4) A free radical substitution reaction
O Na
O 42. The Williamson synthesis involves
(1) A nucleophilic addition
37. + CH3 – C – Cl Product
(2) An electrophilic substitution
Sodium phenoxide
(3) SN2 displacement
O
(4) SN1 displacement
OH O
C – OCH3 43. In the Williamson synthesis of ethers given by the
C – CH3
(1) (2) general equation –
R – X + R'ONa  R – O – R'
O the yield from R – X follows the sequence
Cl (1) CH3X > 1° > 2° > 3°
O – C – CH3
(2) CH3X < 1° < 2° < 3°
(3) (4)
(3) CH3X < 1° < 2° > 3°
(4) CH3X > 1° < 2° < 3°
38. The reaction 44. With conc. HBr ethyl phenyl ether yields

OH (1) Phenol and ethyl bromide

140°C (2) Bromobenzene and ethanol
O Na + CO2 COONa
(3) Phenol and ethane

is called (4) Bromobenzene and ethane

45. The reaction
(1) Schotten Bauman reaction
Me
(2) Kolbe Schmidt reaction NaH O Na Me–I
OH O

(3) Reimer - Tiemann reaction

Can be classified as
(4) Lederer-Manasse reaction
(1) Williamson ether synthesis reaction
(2) Alcohol formation reaction
(3) Dehydration reaction
39.
(4) Williamson alcohol synthesis reaction
HBr
(1) O-salicylic acid (2) O-salicyl Aldehyde ?
46.
O
(3) Picric acid (4) Phenolphthalin
40. Phenol on treatment with methyl chloride in the (1) (2)
presence of anhydrous AlCl3 gives chiefly Br OH HO Br
(1) o-cresol (2) m-cresol
(3) (4)
(3) anisole (4) p-cresol O Br Br O
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47. When glycerol is treated with excess HI, it CH = CH – CHO

produces 49. LiAlH4
H
+ ?
(1) Allyl iodide
CH=CH–CH2–OH
(2) Propane
(1)
(3) Glyceryl triiodide
CH2–CH2–CHO
(4) 2-iodopropane
(2)
48. Which reaction does not produce alcohol among
the following ? CH2–CH2–CH2–OH
(3)
LiAlH4
CH3–C–Cl
(1) H+
O CH2–CH2–CH2–OH
(4)
LiAlH4
CH3–C–OH
(2) H+
50. Which one does not give dichromate test?
O
OH
NaBH 4 (1) (2)
CH3–C–OH +
OH
(3) H
O
(3) OH (4) CH3–OH
(4) None

ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 2 2 4 3 4 3 2 3 3 3 2 2 3 3 2
Que. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. 3 4 2 4 3 4 2 2 3 3 4 3 2 2 3
Que. 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
Ans. 4 2 2 3 4 3 3 2 1 4 3 3 1 1 1
Que. 46 47 48 49 50
Ans. 1 4 3 4 3

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