PRE-MEDICAL

ORGANIC
CHEMISTRY
ENTHUSIAST | LEADER | ACHIEVER

EXERCISE
Alchohol, Phenol and Ether
ENGLISH MEDIUM

Chemistry : Alcohols, Phenols and Ethers ®
Pre-Medical

EXERCISE-I (Conceptual Questions) Build Up Your Understanding

ALCOHOL 6. Select the incorrect option for the following
1. The compound A, B and C in the reaction reaction:
sequence H+
→ CH3– CH – CH3
CH3– CH = CH2 + H2O
PBr3
CH3CH2OH → A 
→ B 
→C alc.KOH Br2
∆ OH
are given by the set
(1) This is an example of NAR of alkene
(1) C2H5Br, CH3CH2OH, CH3CHBr2.
(2) In the first step, protonation of alkene takes
(2) C2H5Br, CH≡CH, CH2=CHBr
place to form carbocation
(3) C2H5Br, CH2=CH2, CH2Br—CH2Br
(3) In the second step, Nucleophilic attack of
(4) C2H5Br, CH3CH2OH, BrCH2—CH2Br water takes place on carbocation
AE0001
(4) In the last step deprotonation takes place to
form an alcohol

®
2. Which of the following alcohols gives a red
colour in Victor Meyer test HC0201
(1) CH3–CH2–CH2–OH 7. For the reduction of aldehydes and ketones into
(2) CH3–CH–OH alcohol the reagent which can be used is/are :
CH3 (1) H2 in presence of Ni, Pt or Pd

(3) (CH3)3C–OH (2) NaBH4

(4) CH3–CH–CH2–CH3 (3) LiAlH4

OH (4) All of these

AE0003 CC0202
8. Which of the following does not reduces the
3. Which of the following does not turn orange
colour of chromic acid to green carboxylic acids into alcohol ?
(1) 1° alcohol (2) 2° alcohol
1.LiAlH4/ether 1.B2H6
(3) 3° alcohol (4) Allyl alcohol (1) (2) +
2.H3O
+
2.H3O
AE0005

4. p, s and t-alcohols can be distinguished by :- ROH H2

(3) NaBH4 (4)
(1) Reimer-Tiemann reaction H+ Catalyst
(2) Tollen's reagent
(3) Lucas test CA0203
(4) Lassaigne's test
AE0006 H2SO4
A
443K
5. Consider the following reaction : 9. CH3CH2OH A and B are
C2H5OH + H2SO4 → Product H2SO4
B
Among the following, which one cannot be 413K
formed as a product under any conditions ? (respectively)

(1) C2H5OSO3H (1) O , CH2 = CH2

(2) H2C=CH2
(2) O , O
(3) HC≡CH
(4) CH3–CH2–O–CH2–CH3 (3) CH2 = CH2, CH2 = CH2
AE0007 (4) CH2 = CH2, O
AE0204
57

® Chemistry : Alcohols, Phenols and Ethers
Pre-Medical
10. Which of the following is insoluble in water ? PHENOL
(1) Ethanol (2) Ethoxyethane 17. Nitration of phenol with conc. H2SO4 followed by
(3) Phenol (4) Pentane nitric acid gives :-
AE0206
OH OH
11. The correct reactivity order towards H–X will be NO2
(1) (2)
(I) OH (II) CH2=CH–CH2OH NO2

(III) CH3–CH2–OH (IV) CH3–CH–CH3 OH OH

OH O2N NO2
(3) (4)
(1) II > I > III > IV (2) IV > III > II > I
(3) II > IV > I > III (4) II > IV > III > I NO2 NO2
AE0196
AE0008
12. Which of the following product will be obtained

®
18. Deoxygenation of phenol can be achieved by
when neopentyl alcohol is treated with conc. HCl
distillation with :-
in presence of ZnCl2.
(1) Raney nickel
(1) t– butyl chloride (2) isobutylene
(2) Lithium aluminium hydride
(3) t– pentyl chloride (4) Neo pentyl chloride
(3) Sodium borohydride
AE0197
(4) Zinc dust
13. For the reaction, AE0009
C2H5OH + HX → C2H5X, the order of 19. Which of the following compounds shows
reactivity is intramolecular hydrogen bonding :-
(1) HI > HCl > HBr (2) HI > HBr > HCl (1) p–Nitrophenol (2) Ethanol
(3) HCl > HBr > HI (4) HBr > HI > HCl (3) o–Nitrophenol (4) Methanamine
AE0203 AE0010

14. Butanenitrile may be prepared by heating O Na⊕

O
(1) Propyl alcohol with KCN 20.
+ CH3—C—Cl ?
(2) Butyl alcohol with KCN
(3) Butyl chloride with KCN Sodium phenate
(4) Propyl chloride with KCN O
HD0205 C–OCH3

15. Which alcohol produces turbidity with Lucas (1)

reagent most slowly
(1) 2–Butanol (2) t–Butyl alcohol O
OH
(3) Isobutyl alcohol (4) Diphenylcarbinol C–CH3
AE0216
(2)
16. Alkyl halides can be obtained by all methods O
excepts O–C–CH3
ZnCl2
(1) CH3—CH2—OH + HCl 
→
(3)
(2) CH2 = CH—CH3 + HBr →
(3) C2H5OH + NaCl → Cl
PCl3
(4) CH3–CH2–OH  →
(4)
HD0001
CA0011
58

Chemistry : Alcohols, Phenols and Ethers ®
Pre-Medical
21. The reaction 26. The final product in the reaction is
(1) KOH, ∆
OH Ph—OH + CCl4 
(2) H⊕
→ product
⊕ ⊕
140° C
ONa+CO
2

→ COONa (1) Salicylaldehyde
(2) Salicylic acid
is called :-
(3) Methyl salicylate
(1) Schotten Bauman reaction
(4) Benzyl chloride
(2) Kolbe Schmidt reaction AH0041
(3) Reimer–Tiemann reaction 27. Phenol on treatment with dil HNO3 at low temp
(4) Wurtz reaction (298 K) gives two products P and Q. P is steam
AE0012 volatile but Q is not. P and Q are respectively.
22. Phenol can be distinguished from ethanol by OH OH

®
reactions with the following except :- NO2
(1) and
(1) Iodine and alkali
(2) Ferric chloride NO2

(3) Acetyl chloride OH OH

(4) Bromine water
(2) and
HD0013
NO2
23. Phenol on treatment with methyl chloride in the NO2

presence of anhydrous AlCl3 gives chiefly :- OH OH

OH NO2
(1) o–cresol (2) m–cresol
(3) and
(3) anisole (4) p–cresol
AE0014 NO2 OH

24. Phenol on heating with NaNO2 and a few drops OH OH

of conc. H2SO4 mainly gives :-

(4) and
(1) p–nitrophenol NO2
(2) p–nitrosophenol NO2

(3) o–nitrophenol AE0207

(4) m–nitrosophenol
ETHER
AE0015
28. The preparation of ethers from alcohols by using
25. Phenol and benzoic acid are distinguished by :- sulphuric acid is called :-
(1) Lucas reagent (1) Williamson's ether Synthesis
(2) Victor Meyer test (2) Williamson's continuous etherification process
(3) Caustic soda (3) Ziesel's method
(4) Sodium bicarbonate (4) Zerewitinoff method
PO0016 AE0236

59

® Chemistry : Alcohols, Phenols and Ethers
Pre-Medical
29. PBr3 Mg/ether H2O/H+ 33. Which of the following does not react with aq.
CH3–CH–CH3 X Y
NaOH :-
OH
(1) Phenol
The final product is :-
(2) Benzoic acid
(1) CH3–CH–OH
(3) CH3COOH
CH
(4) CH3–O–C6H5
(2) CH3–CH2–CH2–OH PO0026
(3) CH3–CH–O–CH–CH3 34. A student tried two reactions for preparing tert-
CH3 CH3 butyl ethyl ether :
(4) CH3–CH2–CH3 CH3
AE0020 (I) C2H5ONa + CH3 – C – Cl

®
CH3
30. In the reaction sequence
A HBr C2 H5 ONa
→ B → Ethoxyethane, CH3
A and B are :- (II) CH3 – C – ONa +CH3 – CH2– Cl
(1) C2H6, C2H5Br CH3
(2) CH4, CH3Br Which reaction will give better yield of tert butyl
(3) CH2=CH2, C2H5Br ether ?
(1) Only I (2) Only II
(4) CH≡CH,CH2=CHBr
(3) Both I & II (4) Neither I nor II
AE0021
D0208
⊕
H
31. CH3–CH2–OH + Ph–CH2–OH 
140° C

→ of
35. Reaction of sodium ethoxide and ethyl iodide will
which is not obtained?
give :-
(1) CH3–CH2–OCH2–CH3
(1) Ether (2) Ethyl alcohol
(2) Ph–CH2–OCH2–Ph
(3) Acetaldehyde (4) Acetic acid
(3) Ph–CH2–O–CH2–CH3
HD0213
(4) Ph–CH2–O–CH2–O–CH3

AE0023 36. The reaction of ethyl iodide with sodium

ethoxide is
32. Oxonium ion of ether has the structure :-
(1) An electrophilic substitution reaction
⊕
(2) A nucleophilic addition reaction
(1) C2H5–O–CH–O–H
(3) A nucleophilic substitution reaction
CH3 H
(4) A free radical substitution reaction
⊕
(2) CH3–CH2–O–CH2–CH3 HD0218
H
37. The Williamson synthesis involves :-
(3) (C2H5)2O → O (1) A nucleophilic addition

⊕
(2) An electrophilic substitution
(4) CH3–CH2–O–CH2–CH2–CH2–O–O–H (3) SN2 displacement
H 1
(4) SN displacement
AE0024 HD0219

60

Chemistry : Alcohols, Phenols and Ethers ®
Pre-Medical
38. In the Williamson synthesis of ethers given by the 39. With conc. HBr ethyl phenyl ether yields :–
general equation – (1) Phenol and ethyl bromide.
R–X + R'ONa → R–O–R' the yield from (2) Bromobenzene and ethanol
R–X follows the sequence :- (3) Phenol and ethane
(1) CH3X > 1° > 2° > 3° (4) Bromobenzene and ethane
(2) CH3X < 1° < 2° < 3° HD0221
(3) CH3X < 1° < 2° > 3°
(4) CH3X > 1° < 2° < 3°
HD0220

EXERCISE-I (Conceptual Questions) ANSWER KEY

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

61

® Chemistry : Alcohols, Phenols and Ethers
Pre-Medical

EXERCISE-II (Previous Year Questions) AIPMT/NEET

AIPMT 2014 NEET(UG) 2017

1. Among the following sets of reactants which one 5. The heating of phenyl–methyl ethers with HI
produces anisole? produces
(1) iodobenzene (2) phenol
(1) CH3CHO ; RMgX
(3) benzene (4) ethyl chlorides
(2) C6H5OH ; NaOH ; CH3I
AE0120
(3) C6H5OH ; neutral FeCl3
(4) C6H5 – CH3 ; CH3COCl; AlCl3 NEET(UG) 2018
6. The compound A on treatment with Na gives B,
AE0105
and with PCl5 gives C. B and C react together to
RE-AIPMT 2015 give diethyl ether. A, B and C are in the order
2. Reaction of phenol with chloroform in presence (1) C2H5OH, C2H6, C2H5Cl

®
of dilute sodium hydroxide finally introduces (2) C2H5OH, C2H5Cl, C2H5ONa
which one of the following functional group ?
(3) C2H5Cl, C2H6, C2H5OH
(1) –CHCl2 (2) –CHO
(4) C2H5OH, C2H5ONa, C2H5Cl
(3) –CH2Cl (4) –COOH
AE0134
AH0109
7. Identify the major products P, Q and R in the
following sequence of reaction :
3. Which of the following reaction(s) can be used for
Anhydrous
the preparation of alkyl halides ? AlCl3 (i) O2
+ CH3CH2CH2Cl P + Q+R
anh.ZnCl2 (ii) H3O /∆
(I) CH3CH2OH + HCl →

(II) CH3CH2OH + HCl → CH2CH2CH3 CHO

(III) (CH3)3COH + HCl →
(1) , , CH3CH2–OH
anh.ZnCl2
(IV) (CH3)2CHOH + HCl →
P Q R
(1) (IV) only (2) (III) and (IV) only
(3) (I), (III) and (IV) only (4) (I) and (II) only
CH2CH2CH3 CHO COOH
AE0284
(2) , ,
NEET-I 2016
4. The reaction P Q R
Me
⊕
NaH
OH → ONa →
Me-I
O CH(CH3)2 OH
(3) , , CH3CH(OH)CH3
Can be classified as :-
P Q R
(1) Williamson ether synthesis reaction

(2) Alcohol formation reaction OH

CH(CH3)2
(3) Dehydration reaction (4) , , CH3–CO–CH3

(4) Williamson alcohol synthesis reaction

P Q R
HD0298 AH0135
62

Chemistry : Alcohols, Phenols and Ethers ®
Pre-Medical
NEET(UG) 2019 10. The major products C and D formed in the
8. The structure of intermediate A in the following following reactions respectively are :-

reaction is :- excess HI
H3C–CH2–CH2–O–C(CH3)3 
∆
→C + D
CH3
CH OH O (1) H3C–CH2–CH2–I and I–C(CH3)3
CH3
O2 H+
A + H3C CH3 (2) H3C–CH2–CH2–OH and I–C(CH3)3
H2O

(3) H3C–CH2–CH2–I and HO–C(CH3)3

CH3

CH (4) H3C–CH2–CH2–OH and HO–C(CH3)3

O
CH3 AE0221

®
(1)
NEET(UG) 2020

CH3 11. Anisole on cleavage with HI gives:

I
H3C–C–O–O–H
(1) + C2H5OH
(2)
OH
CH3
(2) + CH3I
O O CH

CH3 I
(3)
(3) + CH3OH
CH2–O–O–H
HC OH
CH3
(4) (4) + C2H5I

AE0218 AE0417

NEET(UG) 2019 (ODISHA) NEET (UG) 2021(Paper-2)

9. When vapours of a secondary alcohol is passed 12. Which of the following reactions is not possible?
over heated copper at 573 K, the product
(1) HC ≡ CH + NaOH → HC ≡ CNa + H2O
formed is :-

(1) a carboxylic acid (2) + HCl Cl

(2) an aldehyde
(3) C2H5OH + NaCl → C2H5Cl
(3) a ketone
(4) All of the these
(4) an alkene
HC0244
CC0220
63

® Chemistry : Alcohols, Phenols and Ethers
Pre-Medical
NEET(UG) 2022 15. The major products formed in the following
13. Given below are two statements : reaction are
Statement I : H3C
In Lucas test, primary, secondary and tertiary O
H3C H3C + HI → ?
alcohols are distinguished on the basis of their
reactivity with conc. HCl + ZnCl2, known as H3C
Lucas Reagent.
H3C
Statement II:
(1) CH2, CH3I
Primary alcohols are most reactive and
immediately produce turbidity at room H3C
temperature on reaction with Lucas Reagent.
H3C
In the light of the above statements, choose the
(2) H C I, CH3–OH
most appropriate answer from the options given 3

below: H3C

®
(1) Both Statement I and Statement II are
H3C
incorrect.
(3) H C OH, CH3–OH
(2) Statement I is correct but Statement II is 3

H3C
incorrect.
(3) Statement I is incorrect but Statement II is H3C
correct (4) H C
3 OH, CH3–I
(4) Both Statement I and Statement II are H3C
correct
AE0245 AE0250

NEET(UG) 2022 (Overseas) NEET(UG) 2023

14. Given below are two statements : 16. Consider the following reaction and identify the

Statement - I : The product of reaction of product (P).

phenol with bromine depends on the nature of CH3–CH–CH–CH3
solvent. CH3 OH 
HBr
→ Product (P)
Statement - II : Reaction of phenol with 3-Methylbutan-2-ol
bromine in CHCI3 gives monosubstituted bromo
derivative whereas reaction of phenol with (1) CH3CH=CH–CH3
bromine water yields trisubstituted bromo (2) CH3–CH–CH–CH3
derivative of phenol.
In light of the above statements, choose the most CH3 Br

appropriate answer from the options given

below: CH3
(1) Statement-I is incorrect and Statement-II (3) CH3–C–CH2Br
is correct
CH3
(2) Both Statement-I and Statement–II are
correct
Br
(3) Both Statement-I and Statement–II are (4)
incorrect CH3–C–CH2–CH3

(4) Statement-I is correct and Statement-II is CH3

incorrect
AE0404
AE0249
64

Chemistry : Alcohols, Phenols and Ethers ®
Pre-Medical
17. Consider the following reaction NEET(UG) 2023 (Manipur)

HI 19. Reagents which can be used to convert alcohols

CH2–O A+B
∆ to carboxylic acids, are
(A) CrO3 – H2SO4
Identify products A and B :- (B) K2Cr2O7 + H2SO4
(C) KMnO4 + KOH/H3O+
(1) A= CH2OH and B = I
(D) Cu, 573 K
(E) CrO3, (CH3CO)2O

(2) A= CH2I and B = OH Choose the most appropriate answer from the
options given below :
(1) (B), (C) and (D) only
(3) A= CH3 and B = I (2) (B), (D) and (E) only

®
(3) (A), (B) and (C) only
(4) A= CH3 and B = OH (4) (A), (B) and (E) only
AE0407
AE0405
18. Which amongst the following will be most readily
dehydrated under acidic conditions ?
NO2
OH OH H

(1) H C (2) OH
3
H OH
NO2 NO2 OH

(3) (4) CH3

OH H
HD0406

EXERCISE-II (Previous Year Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 2 2 3 1 2 4 4 2 3 1 2 4 2 2 2
Que. 16 17 18 19
Ans. 4 2 1 3
65

® Chemistry : Alcohols, Phenols and Ethers
Pre-Medical

EXERCISE-III (Analytical Questions) Master Your Understanding

1. The structures of the compounds / ions A, B 4. In following two columns :
and C in the reaction sequence are given by Column-I
the set :- (a) CH3–CH2–Br + HS → CH3–CH2–SH + Br
— –

Cl OH
HCl
B (b) (CH3)2C=CH2 + HOCl → (CH3)2C–CH2–Cl
2OH
A
360° CH3I (c) CH3–CH2–Br + –OH → CH2=CH2+H2O + Br–
C
(d) (CH3)3C–CH2–OH + H–Br →

(1) OH, Cl, (CH3)2CBrCH2–CH3 + H2O

CH3
Cl OH

O, OH, OCH3 (e) →

NaOH

®
(2)

Column-II
O, Cl, I (1) Nucleophilic substitution
(3)
(2) Elimination
(3) Electrophilic substitution
(4) O, OH, I
(4) Electrophilic additon
(5) Rearrangement reaction
HD0151
(1) a, d → 1 , b → 4, c → 2 , e → 1
2. In the reaction sequence — (2) e, a, d → 1 , b → 4, c → 3
(3) a, e → 1 , b → 4, c → 2 , d → 5
NaOH CH3I
SO3Na A B HI C+D (4) a, c → 1 , b → 4, e → 3 , d → 5
350°C
HD0403
A, B, C and D are given by the set :-
5. Identify 'Z' in the following reaction series,
(1) Sodium phenate, anisole, C6H5I, CH3OH aq. NaOH Al O
CH3.CH2CH2Br
→ (X) 
2 3
→ (Y)
Heat
(2) Sodium phenate, phenetole, C2H5I, C6H5OH
Cl /H O

2 2
→ (Z)
(3) Sodium phenate, anisole, C6H5OH, CH3I

(4) Sodium phenate, phenetole, C6H5I, C2H5OH (1) Mixture of CH3–CH–CH2 and CH3–CH–CH2
Cl Cl OH OH
HD0153
3. Which of the following ether can not be (2) CH3–CH–CH2
prepared by Williamson's method :-
OH Cl
(1) Ditertbutyl ether
(3) CH3–CH–CH2
(2) Ethyl-tert-butyl ether
Cl OH
(3) Anisole
(4) CH3–CH–CH2
(4) 1 & 2 Both
AE0355 Cl Cl

HD0045

66

Chemistry : Alcohols, Phenols and Ethers ®
Pre-Medical
6. CH3–CH2–OH NaBr (A) Alc.KOH (B) HBr (C)
 → →  → 10. In the reaction :
H2 SO4 ∆
CH3
A, B and C are respectively - CH3–CH–CH2–O–CH2–CH3+HI → .........
(1) CH3CH2HSO4 , CH2=CH2 , BrCH2–CH2–Br which of following compounds will be formed :
(1) CH3–CH–CH3 + CH3–CH2–OH
(2) CH3–CH2–Br, CH2=CH2, CH3–CH2–Br
CH3
(3)CH3–CH2–OCH2–CH3, CH2=CH2, CH3–CH2
(2) CH3–CH–CH2–OH + CH3–CH3
Br
CH3
(4) CH2=CH2, CH3–CH2–OH, CH3–CH2–Br (3) CH3–CH–CH2–OH + CH3–CH2–I
HD0066 CH3

7. Best method to convert alcohol into alkyl (4) CH3–CH–CH2–I + CH3–CH2–OH

CH3

®
chloride is -
AE0238
(1) ROH + SOCl2 → R–Cl + SO2 + HCl

(2) R–OH + PCl3 → R–Cl 11. H2COH.CH2OH on heating with periodic acid
gives :-
(3) R–OH + PCl5 → R–Cl
H
(4) R–OH + HCl → R–Cl + H2O (1) 2 C=O (2) 2CO2
H
HD0072 CHO
(3) 2HCOOH (4)
HBr CHO
8. Major product ?
OH AE0081

Br 12. Consider the following reaction,

(1) (2)
Br PBr 3
ethanol → alc. KOH
X  → Y

( i ) H2 SO4 room temperature

CH2Br  → Z;
(3) (4) ( ii ) H2O

Br the product Z is :-

HD0073 (1) CH3CH2OH

(2) CH2 = CH2
9. The major organic products of reaction are
(3) CH3CH2 – O – CH2 – CH3
CH3–O–CH(CH3)2 + HI →
(4) CH3 – CH2 – O – SO3H
(1) CH3OH +(CH3)2CHI AE0082
(2) ICH2–O–CH(CH3)2 13. Consider the following reaction :
CH3Cl KMnO4
(3) CH3–O–C(CH3)2 Phenol Zn dust X Y Z
∆ Anhydrous ∆
I AlCl3
the product Z is :-
(4) CH3I+ (CH3)2CHOH (1) Benzene (2) Toluene
AE0233 (3) Benzaldehyde (4) Benzoic acid
AH0084

67

® Chemistry : Alcohols, Phenols and Ethers
Pre-Medical
14. When glycerol is treated with excess of HI, it 16. Among the following ethers, which one will
produces :- produce methyl alcohol on treatement with hot
(1) allyl iodide (2) propene
concentrated HI ?
(3) glyceryl triiodide (4) 2-iodopropane
(1) CH3–CH–CH2–O–CH3
AE0087
CH3
15. In the following reactions,
CH3 (2) CH3–CH2–CH2–CH2–O–CH3
+
H /Heat
(a) CH3–CH–CH–CH3 A B
Major + Minor (3) CH3–CH2–CH–O–CH3
product product
OH CH3
HBr, dark
(b) A in absence of peroxide
C D
Major + Minor
product product CH3
(4) CH3–C–O–CH3
the major products (A) and (C) are respectively :-
CH3 CH3 CH3

®
(1) CH2=C–CH2–CH3 and CH2–CH–CH2–CH3 AE0265
Br
CH3 CH3

(2) CH3–C=CH–CH3 and CH3–C–CH2–CH3

Br
CH3 CH3
(3) CH3–C=CH–CH3 and CH3–CH–CH–CH3
Br
CH3 CH3

(4) CH2=C–CH2–CH3 and CH3–C–CH2–CH3

Br
AE0091

EXERCISE-III (Analytical Questions) ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. 2 3 1 1 2 2 1 2 4 3 1 4 4 4 2
Que. 16
Ans. 4

68