1

MANZIL
Alchol Phenol and Ether
Practice Sheet-1
1. Arrange the following compounds in 4. The major product of the following reaction
increasing order of C – OH bond length: is:
methanol, phenol, p–ethoxyphenol H 3C OH
(A) phenol < methanol < p–ethoxyphenol
(B) methanol < p–ethoxyphenol < phenol
(C) methanol < phenol < p–ethoxyphenol H 3C H 3C
(D) phenol < p-ethoxyphenol < methanol  
dil.H 2SO 4

H 3C OH
2. Consider the following reactions:
(A) H 3 C OH
(A) Cl CH 3
OH
CH 3

anhyd.AlCl2

(B) + Cl2 (excess)

(B)
OH
Cl Cl H 3C
CH 3

anhyd.AlCl2
Cl Cl OH
dark H 3C
Cl OH
Cl
(C) + CH2 = CH – Cl (C)
H 3C HO CH
2


anhyd
 CH 3
AlCl2 CH CH 2

(D) + CH2 = CH – CH2Cl

(D)

anhyd
AlCl 2
 CH 2 CH CH 2 H 3C OH
CH 3
3. Which of these reactions are possible?
5. Heating of 2-chloro-1-phenylbutane with
(A) (b), (c) and (d)
EtOK/EtOH gives X as the major product.
(B) (a) and (b)
Reaction of X with Hg (OAC)2/H2O
(C) (a) and (d)
followed by NaBH4 gives Y as the major
(D) (b) and (d)
product. Y is:
(A) Ph
OH
OH

(B) Ph
 2

OH O

(C) Ph
(A)
(D) Ph HO
O
6. Which of the following compounds reacts
with ethylmagnesium bromide and also
decolourizes bromine water solution: (B)
OCH 3 HO
OH O
(A) CH 2
(C)
CN Cl
CH 2 CO 2 CH 3
(B) O

OH (D)
(C) Cl

10. The major product of the following reaction

CN O is:
OH
(D)
CH 2 OH

H 2SO 4 (cat.)
CHCl3
CO 2 Et
7. Consider the following reaction:
OH
(A) (CH3)3 CCH (OH) CH3 
conc.H 2SO 4

(B) (CH3)2CHCH (Br) CH3 

alc.KOH

  O
(C) (CH3)2 CH (Br) CH3 
(CH 3 )3 O K
 (A)
(D) (CH 3 )2 C CH 2 CHO  
 O
OH OH

8. Which of these reaction (s) will not produce

saytzeff product? (B) OEt
(A) (d) only
(B) (b) and (d) O
(C) (a), (c) and (d) O
(D) (c) only (C)

9. The major product of the following reaction COOH

is : O
(D)
HO 
(1) CrO3
(2)SOCl 2 / 
(3)  CO 2 Et
HO

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CH 2OH
11. What will be the major product when m-
cresol is product when m-cresol is reacted
with propargyl bromide (HC  C – CH2Br) (C)
in presence of K2CO3 in acetone?
Cl
O
CHCl2

(A)
CH 3 (D)
OH Cl

(B) 13. The major product of the following reaction

CH 3 is:
OH HO  (i) HCl

(ii) AlCl3 (Anhyd)

(C) Cl
CH 3 (A)
OH
HO
(B)

(D)
CH 3
Cl
(C)
12. The major product of the following reaction
is:
Cl
CH 3 (D)

(1) Cl 2 / h

(2) H 2 O, 

14. Coupling of benzene diazonium chloride
Cl with 1-naphthol in alkaline medium will
CHO give:
OH

(A)
Cl
CO 2 H N
(A)
N
(B)
Cl

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Br

N (A)
Br – CHCH 3
N
(B) HO OH

(B)
Br – CHCH 3
Br

N (C)
CH 2CH 2 Br
N
OH
(C)
(D)
CH 2CH 2 Br
OH
OH
17. The major product of the following reaction
is:
(D) OH
N
N

Br2 (excess)

SO 3 H
15. What is the product of following reaction? OH
Hex  3  ynal 
(i) NaBH 4
(ii) PBr3

(iii) Mg/ether
(iv) CO 2 / H3 O 
(A) Br Br
COOH
(A) Br
(B) OH
COOH
Br Br
COOH
(C) (B)
(D) Br
COOH
OH
16. The major product of the following Br
reaction is: (C)
OCH 3
SO 3 H
Conc HBr  excess 

 heat

CH CH 2

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OH OH
Br Br
(D) (C)

SO 3 H NC I
I
18. The major product in the following
conversion is
(D)
CH 3O CH CH CH 3
NC I

HBr(excess)
Heat
20. Which is the most suitable reagent for the
(A) HO CH 2 CH CH 3 following transformation?
Br OH
CH3 – CH = CH – CH2 – CH – CH3  CH3
(B) CH 3 O CH 2 CH CH 3
– CH = CH – CH2CO2H
Br (A) alkaline KMnO4
(B) Tollen’s neagent
(C) CH 3 O CH CH 2 CH 3
(C) I2/NaOH
Br (D) CrO2Cl2/CS2
(D) HO CH CH 2 CH 3
21. The major product of the following reaction
Br CH 3
OH (i) aq. NaOH
19. The major product of the following reaction 
(ii) CH 3 I
is :
O CH 3
OCH 3
(A)

HI(excess)

NC O CH 3
OH
OH
(B)
CH 3
(A)
CH 3
OH
NC OH
I
(C)
CH 3
(B)
CH 3
NC OH
OH
(D)
CH 3

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ANSWERS KEY
1. (D)
2. ()
3. (D)
4. (B)
5. (C)
6. (B,C)
7. ()
8. (D)
9. (B)
10. (A)
11. (A)
12. (C)
13. (B)
14. (C)
15. (B)
16. (B)
17. (B)
18. (D)
19. (A)
20. (C)
21. (A)

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