Alcohols, Phenols & Ethers

1
1. Alcohols boil at higher temperature than
the corresponding hydrocarbons due to

(A) intermolecular hydrogen bonding

(B) intramolecular hydrogen bonding
(C) van der Waal’s forces of attraction
(D) dipole – dipole interactions

2
Ans: (A)

Ans: (A)

3
CH 2  CH  OH

2. Vinyl carbinol is ____________

(A) CH 3  CH  CH  OH
(B) CH 3  C(OH)  CH 2
(C) CH2  CH  CH2OH
(D) CH 3  CH  CH  OH

4
CH 2  CH  OH

Carbinol is CH3OH, which is attached to

vinyl group. Therefore Ans is (C)

CH2  CH  CH2OH

5
3. 1-propanol and 2-propanol can be best
distinguished by
(A) Oxidation with alk. KMnO4 followed by
reaction with Fehling solution
(B) Oxidation with acidic dichromate followed
by reaction with Fehling solution
(C) Oxidation by heating with copper followed
by reaction with Fehling solution.
(D) Oxidation with conc. H2SO4 followed by
reaction with Fehling solution.

6
CH3  CH 2  CH 2  OH 
Cu

 CH 3 CH 2 CHO 
Fehling
Soln
s
red colour.
CH 3  CH  CH 3 
Cu

 CH 3  COCH 3 
Fehling
So ln
 No reaction.
|
OH

Ans (C)

7
4. Phenyl magnesium bromide reacts with
methanol to give

(A) a mixture of anisols and Mg(OH)Br

(B) a mixture of benzene and Mg(OMe)Br
(C) a mixture of toluene and Mg (OH)Br
(D) a mixture of phenol and Mg(OH)Br

8
C 6 H 5 MgBr  CH 3 OH 
 C 6 H 6  Mg(OMe)Br

Ans: (B)

9
5) Reduction of aldehyde, RCHO with
sodium and ethanol gives
(A) 1° alcohol
(B) 2° alcohol
(C) 3° alcohol
(D) alkane

10
Ans: A) 1° alcohol

11
6) Which of the following compound will
produce a primary alcohol on reaction with
Grignard reagent followed by hydrolysis?
(A) acetone (B)methyl cyanide
(C) ethylene oxide (D) ethyl acetate

12
Grignard reagent is converted into 1° alcohol
using H−CHO or ethyleneoxide
1° alcohol containing 2 carbon atoms more than
the Grignard reagent can be obtained by treating
with R-Mg-X with ethylene oxide followed by
acid hydrolysis,

Ans: (C) ethylene oxide

13
7) The compound X in the reaction is

(A) (B)

(C) (CH3)2CH(OMgBr) (D)

14
Ans:
(C) (CH3)2CH(OMgBr)

15
8. In the following sequence of reaction:
The compound D is
P  I2
CH3CH 2CH 2 OH   A 
Mg
ether
 B 
HCHO
 C 
H2O
D

(A) 2-propanal (B) 1-propanal

(C) 1-butanol (D) 2-butanal

16
CH 3CH 2 CH 2 OH 
P/I 2
 CH 3CH 2 CH 2 I 
Mg
ether
 CH 3CH 2 CH 3MgI

HCHO
 CH 3CH 2 CH 2 CH 2  OMgI
H2O 1-butanol +Mg(OH)I

Ans: (C)

17
9. Which one of the following is most acidic?

(A)CH3OH
(B)CH3CH2OH
(C) (CH3)2CHOH
(D) (CH3)3COH

18
Due to the electron releasing groups in other
compounds.
Ans: (a) CH3OH

19
10. Which one of the following is most acidic?

(A)H2O (B) CH3CH2OH

(C) CH3OCH3 (D) C6H5OH

20
C6H5OH
Due the presence of more electro negative
Sp2 hybridised carbon of benzene.

Ans: (D)

21
11)The reactivity of alcohol towards
active metal is

(A) 3° > 2° > 1°

(B) 1° > 2° > 3°
(C) 3° > 1° > 2°
(D) 2° < 3° < 1°
22
When an alcohol reacts with a metal, for
example, sodium, bond between RO−H is
broken for which 1° alcohols are most
reactive since 1° alcohols are more acidic
than 3° alcohols which is least reactive.
Ans (B) 1° > 2° > 3°

23
12) Pentan-3-ol is an example of –

(A)1 alcohol
(B) 2 alcohol
(C) 3 alcohol
(D) aromatic alcohol

24
Ans: (B)

25
13. How many optically active isomers are
possible for butane-2, 3-diol?

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

26
Ans: (B) There are 2 chiral carbons but due to
the presence of symmetry, the compound
shows two optically active isomers only
CH3 CH3

H C OH H C OH
H C OH HO C H

CH3 CH3

27
14) The order of reactivity of a Grignard
reagent with the following is
I) CH3-CO-CH3
II) CH3-CHO
III) C6H5-CO-C6H5
(A) II > III > I (B) I > III > II
(C) II > I > III (D) all react with same rate

28
Reactivity is high when steric hindrance
is the least.

C) II > I > III

29
15. 0.037 g of an alcohol was added to CH3MgI
and the gas evolved measured 11.2 cm3 at
STP. What is the molecular formula of the
alcohol?

(A)C4H10O (B) C4H8O

(C) C5H12O (D) C5H10O

30
• C4H10O

11.2 cm3 
 0.037 g alc
of alc
•  22400 cm3 of the gas liberated by

0.037  22400
  74 g
11.2
•  C4H10O

Ans: (A)

31
16. In the following sequence of reaction.

A  B 
Cu
573
 C  (CH 3 ) 3 COH
HBr aq.KOH

The compound A is

(A)CH3CH2CH2CH2OH
(B) (CH3)2CHOH
(C) (CH3)3COH
(D) CH3CH2COCH2CH3

32
Tertiary alcohols undergo dehydration to
give an alkene ,2-methyl propene which on
reaction with HBr gives addition product
according to Mark Rule. That on KOH
treatment gives tertiary butyl alcohol
Ans: (C)

33
17. Which of the following has highest
Boiling ?

(A) C4H9Cl (B) C4H9OH

CH 3  CH  CH 2  CH 2OH
(C) C4H9Br (D) |
OH

34
Ans: (D)
Dihydric alcohols have highest B.Pt due to
extensive intermolecular H-bonding

35
18. CH3  CH2  CH2Br 
alc. KOH
 X  BH3
H 2 O 2 / NaOH
 Y.

The compound Y is

(A) Propene (B) n-propylalcohol

(C) propane (D) n-propyl borate

36
I step is de hydrohalogenation and an alkene
is obtained
II step is alkene on hydroboration oxidation
gives an alcohol against to markovnikov’s
rule.

Ans: (B)

37
19. Which of the following reagents is used in
the conversion of primary alcohol to
aldehydes only?

(A)Corey’s reagent (B) Lucas reagent

(C) Baeyer’s reagent (D) Victor meyer’s reagent

38
Ans (A): Corey’s reagent PCC

39
20) The following structure on
oxymercuration-reduction gives

a) b)

c) d)

40
Oxymercuration –reduction reagent is Mercuric acetate in THF
and water and reduction with NaBH4 which takes place
according to Mark Rule

Mark Rule

Ans: A)

41
21)Which of the following functional group
cannot be reduced to alcohol using
sodium borohydride in ethanoic solution?

a) R – CHO
b) R – CO – R
c) R – COOH
d) RCOCl

42
NaBH4 is a mild reducing agent
NaBH4 can reduce aldehyde, ketones,
acid chlorides to alcohols but not acids or
ethers.

Ans: c) R−COOH

43
22) Which of the following is correct order
of solubility of alcohols in water?
A)isopropyl alcohol > n – propyl alcohol > ethyl
alcohol
B) isopropyl alcohol > ethyl alcohol > n – propyl
alcohol
C) isopropyl alcohol < n – propyl alcohol > ethyl
alcohol
D) n – propyl alcohol < isoporpyl alcohol < ethyl
alcohol

44
Branching increases solubility, straight
chain alcohols are less soluble. This is
due to the surface area of non-polar
hydrocarbon part decreases and solubility
increases.

Ans:
c) Isopropyl alcohol > ethylalcohol >
propyl alcohols
45
23) The order of reactivity of hydrogen
halide towards ROH is

a) HI > HBr > HCl

b) HI < HBr < HCl
c) HI > HBr < HCl
d) HI < HBr < HCl
46
As we move from HCl to HBr to HI, acid
strength increases and bond strength
decreases.

Ans: a) HI > HBr > HCl

47
24. Which of the following reacts with
sodium bicarbonate?

A) phenol B) water
C) alcohol D) picric acid.

48
is an acid stronger than H2CO3 or
HCO3-. Hence it reacts with
NaHCO3 to liberate CO2.
Ans: D) picric acid
49
25. A trihydric phenol is –

A) catechol B) phloroglucinol
C) quinol D) resorcinol

50
Ans:

B)

51
26.Match the acids and their pKa
values
P] p-cresol 1] 7.15
Q] p-nitrophenol 2] 0.71
R] phenol 3] 9.98
S] picric acid 4] 10.14
A) P-4, Q-1, R-3, S-2
B) P-2, Q-1, R-3, S-4
C) P-3, Q-1, R-2, S-4
D) P-1, Q-3,R-4, S-2
52
Cresol is weaker acid than phenol,
has higher pKa value than phenol.
Nitrophenol is stronger acid than
phenol, has lower pKa value. Picric
acid is the strongest acid, has
lowest pKa value.
Ans: A) P-4, Q-1, R-3, S-2

53
27.When phenol/salicylic acid is
shaken with bromine water, the
white precipitate formed is-

A) 2,4,6-trinitrotoluene
B) 2,4,6-trinitrophenol
C) 2,4,6-tribromophenol
D) 2,4,6-tribromotoluene
54
Both phenol and salicylic acid
have ring activating –OH group.
Hence both form tribromoderivative
with bromine water.
Ans: C) 2, 4, 6-tribromophenol

55
28.Which of the following gives a
tribromo derivative when treated
with bromine water?

A) m-cresol B) o-cresol
C) p-cresol D) benzyl alcohol

56
m-cresol is

It has all o and p positions free for

bromination. Hence forms a
tribromo derivative.
Ans: A) m-cresol

57
29. The number of alcoholic and
ethereal isomers possible for
C4H10O are

A) 4 and 3 B) 3 and 2
C) 3 and 4 D) 4 and 2

58
With C4H10O – four butyl alcohols
and 3 isomeric ethers are possible.

Ans:
A) 4 and 3

59
30. A compound X reacts with phthalic anhydride
in presence of conc. H2SO4 forming the
compound Y which gives pink colour with
NaOH solution. The compound Y is

(A)Phenol (B) Phenolphthalein

(C) toluene (D) o-cresol

60
X = phenol, Y = phenolphthalein

Ans: (B)

61
31. Identify the product ‘Y’.
H
O
LiAlH4 CH2N2
X Y

A) benzyl alcohol
B) anisole
C) benzoic acid
D) benzyl methyl ether
62
For diazomethane no catalyst is
required.
Ans:
D) Benzyl methyl ether
63
32. When phenol is converted to salicylaldehyde
by treating it with CHCl3 and NaOH. The
reaction is called as 

(A)Kolbe’s reaction
(B) Friedel Crafts reaction
(C) Reimer Tiemann reaction
(D) Fries reaction

64
Reimer Tiemann reaction
Ans: (C)

65
33. O-nitrophenol and p-nitrophenol are
separated by

(A) steam distillation (B) ordinary distillation

(C) fractional distillation (D) solvent extraction

66
Stream distillation, more volatile O-nitrophenol
due to intra molecular H-bond gets separated
easily.
Ans:(A)

67
34. In the reaction
C6 H6  X 
only AlCl3
 Y 
O2

H2SO4
 phenol  acetone
only

heat
Z

The compound Y in the above reaction is

(A) Isopropyl benzene (B) Ethyl benzene

(C) Acetophenone (D) Toluene

68
Ans: (A)

69
35. The compound C4H10O(X) is produced by
the reaction of conc. H2SO4 / H2O on alkene,
and X is not resolvable into optical isomers.
The X compound is

(A)2-methyl propan-2-ol
(B) 2-methyl propan-1-ol
(C) 2, 2 dimethyl ethan-1-ol
(D) 2-methyl butan-2-ol

70
Ans: (A)

71
36. In the following compounds

Order of acidity is
(A) (III) > IV > I > II (B) I > IV > III > II
(C) II > I > III > IV (D) IV > III > I > II
72
Ans: (D)

73
37. When ethoxy ethane is treated with
excess of HI at 373 K the product /
products formed are

(A) C2H5OH + C2H5I (B) C2H5I

(C) C2H6 + C2H5I (D) C4H10

74
Ans: (B) C2H5I

75
38. Diethyl ether is not isomeric with

A) butanal
B) 2-butanol
C) methyl n-propyl ether
D) buta-1-ol

76
For C2H5OC2H5 ; CH3CH2CH2CH2OH,
CH3CH(OH)CH2CH3 and
CH3O-CH2CH2CH3 are all isomers
but not CH3CH2CH2CHO (butanal)

Ans: A) butanal

77
39. dibenzyl ether is heated with (a)
1mole HI and (b) excess HI the
products formed are
a b
A 2molC6H5CH2OH C6H5CH2OH+C6H5CH2I
B C6H5CH2OH+C6H5CH2I 2mol C6H5CH2I
C 2mol C H CH I C6H5CH2OH+C6H5CH2I
6 5 2

D 2mol C6H5CH2I 2mol C6H5CH2OH

78
Ans:
B) C6H5CH2OH + C2H5CH2I,
2 mol C6H5CH2I

79
40. Aspirin is the acetylated product of

A) o-hydroxybenzoic acid
B) o-hydroxy benzene
C) m-hydroxybenzoicacid
D) o-hydroxybenzaldehyde

80
is aspirin, obtained by acetylation of

o-hydroxy benzoic acid

Ans: A) o-hydroxybenzoic acid
81
41. 2-phenylethanol is prepared
using
A) phenyl magnesium bromide and
ethylene oxide
B) phenyl magnesium bromide and
ethylene glycol
C) phenyl magnesium bromide and
ethyl alcohol
D) methyl magnesium bromide and
benzaldehyde
82
C6H5CH2CH2OH is 2-phenylethanol
(2) (1)

Ans: A) Phenyl magnesium bromide

and ethylene oxide

83
42. Identify the products formed
when t-butyl methyl ether is
heated with limited conc.HI

A) t-butyl alcohol & methyl iodide

B) t-butyl iodide & methyl alcohol
C) t-butyl iodide & methyl iodide
D) t-butyl alcohol & methyl alcohol
84
Ans:
b) t-butyliodide and methyl alcohol

85
43. In the reaction C 6 H 5 OCH 3  HI  373
 K A  B

The products A and B respectively are

(A)Iodobenzene and methanol

(B) Phenol and Iodomethane
(C) Benzene and Methoxy iodide
(D) Benzene and methanol

86
The bond between -O-CH3 is weaker than
-O-C6H5 because in-O-C6H5 the carbon group is
sp2 hybridised and oxygen attains partial double
bond character through resonance.

Ans: (B) Phenol and Iodomethane

87
44. During the reaction (CH3 )3 C  Cl  CH3ONa 
A
The main product A is

(A) Isobutene (B) tes butyl ether

(C) Isobutane (D) ter butyl ether

88
For the preparation of unsymmetrical ethers,
the alkyl halides should be primary, whereas
the alkoxides may be 1, 2 or 3. Ether is
not formed. Elimination competes over
substitution reaction. Hence the answer is
Ans: (A) Isobutene

89
45. During the Friedel crafts reaction of
anisole with acetyl chloride in presence of
anhy AlCl3, the major product obtained is

(A)m-methoxy acetophenone
(B) o-methoxy acetophenone
(C) p-methoxy acetophenone
(D) p-methylanisole

90
Ans: (C) p-methoxy acetophenone

91
46. What is the major product obtained when

is heated

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

92
C6H4 (OH)-O- bond is stronger bond than the
other group. Hence the bond is C6H4 (OH)-O- is
not cleaved.

Ans: (A)

93
47. Match the structures of the compounds given in
Column I with the name of the compounds given in Column
II. Column I Column II
(a) Hydroquinone
(i)
(b) Catechol
(ii)
(c) o-Cresol
(iii)
(d) Quinone
(iv) (e)Resorcinol
(f) Anisole
(v)
48. Match the items of column I with items of column II.
Column I Column II
(a) Neutral ferric chloride
(i)Antifreeze used in car engine
(b) Glycerol
(ii) Solvent used in perfumes
(c) Methanol
(iii) Starting material for picric
acid
(iv) Wood spirit (d) Phenol

(v) Reagent used for detection (e) Ethleneglycol phenolic

of phenols group
(vi) By product of soap industry (f) Ethanol used in
cosmetics
95
49. The compound which is also known as
carbolic acid is

(A)Phenol (B) Benzene

(C) cresol (D) Toluene

96
Ans: A) Phenol

97
50. The IUPAC name of m-Cresol is

(A) 3-chlorophenol (B) 3-Methoxyphenol

(C) 3-methyl phenol (D) benzene -1, 3-diol

98
Ans: (C) 3-methyl phenol

99
51.In the following reaction:


Zn
 A 
Oleum
NaOH
 B 
NaOH
573 K
 C 
HCl
D 
H 2 / Ni
E

The compound E in the reaction?

(A)Benzene (B) Phenol

(C) Cyclohexanol (D) Cyclohexane

100
Benzene on fusion with Oleum and NaOH gives
Sod. Benzene Sulphonate

Ans: (C) Cyclohexanol

101
52.Phenol condenses with HCHO in the
presence of dil acid to form the polymer

(A)Bakelite (B) Buna-S

(C) Teflon (D) Melamine

102
Ans(A) Bakelite

103
53. How will you distinguish between phenol
and Benzyl alcohol?

(A)using neutral FeCl3

(B) using acidic FeCl3
(C) using neutral FeCl2
(D) using acidic FeCl2

104
All phenols give violet colour with neutral
FeCl3.Fe(C6H5O)3 is violet in colour.

Ans: (A)

105
54. When phenol reacts with Br2 in CS2 at 0C,
the major product obtained is

(A) 2-bromo phenol (B) 3-bromo phenol

(C) 4-bromo phenol (D) 2, 4, 6 tribromo phenol

106
Ans (C): 4-bromo phenol

107
55. The reaction of CH3CH = CH OH
with HBr gives

(A)CH3CHBrCH2 OH
(B) CH3  CH2CHBr OH
(C) CH3CHBrCH2 Br
(D) CH3CH2CHBr Br

108
Ans: (B)

109
56. The IUPAC name of the ether
CH3OCH(CH3)2

(A)1-methoxy propane
(B) propoxy methane
(C) 2-methoxy propane
(D) isopropoxy methane

110
Ans: (C) 2-methoxy propane

111
57. The reactants required for the preparation
of ter-butyl ethyl ether by Williamson’s
reaction are

(A) ter butyl chloride + sodium ethoxide

(B) sodium ter butoxide + ethyl chloride
(C) ter butyl alcohol + ethyl chloride
(D) ethyl alcohol + ter. butyl chloride

112
Ans: (B) sodium ter butoxide + ethyl chloride

113
58) Alcohol are obtained from alkenes by
a) hydrolysis with dilute H2SO4
b) hydration with aqueous KOH
c) hydration with alkaline KMnO4
d) Hydration using conc. H2SO4 and hydrolysis

114
Alkenes alcohol is by hydration using
concentrated H2SO4 and hydrolysis.

Ans: d) Hydration using conc. H2SO4 and

hydrolysis

115
59) A reaction between alcohol and organic
acid to form ester involves
a) the cleavage of O – H bond of acid
b) the cleavage of C–O bond of alcohol
c) the formation of bond between oxygen
of COO group of acid and carbon of
alcohol
d) the cleavage of C–OH bond of acid
116
Ans:
d) Cleavage of C−OH bond of the acid

117
60)When phenyl magnesium bromide
reacts with t-butanol the product
would be

a) benzene
b) phenol
c) t-butyl benzene
d) t-butyl phenyl ether
118
(CH3)3C−OH reacts with C6H5MgBr to
form benzene, because the alcohol has
acidic H atom in its –OH group.

Ans: A) benzene

119
61) The compound which gives the most
stable carbocation on dehydration is

A) B)

C) D)

120
3° carbocations are the most stable.

Ans:B) (CH3)3C−OH

121
62) pent-3-en-2-ol is converted into
pent-3-en-2-one when treated with

a) Jones’ reagent
b) potassium dichromate
c) potassium permanganate
d) LiAlH4
122
This reaction is done by using Jones
reagent.
Ans: a) Jones reagent

123
63) The order of dehydration of following
alcohols is
i) ii)

iii) iv)

A) I < II < III < IV B) I > II > III > IV

C) III < II < I < IV D) II < III < IV < I
124
Allylic and 3° alcohols undergo
dehydration the fastest.

Ans: c) III < II < I < IV

125
64) Hydrogen bonding is maximum in

A) ethanol
B) diethyl ether
C) ethylchloride
D) triethylamine

126
Ans: a) Ethanol

127
65) The dehydration of butanol–2 gives

A. 1 – butene only
B. 2 – butene only
C. both 1 – butene and 2 – butene
with 1–butene as major product
D. both 1 – butene and 2 – butene
with 2–butene as major product
128
Ans:
d) both 1 – butene and 2 – butene with
2 – butene as major product

129
66) A mixture of methanol vapour and air
is passed over heated copper. The
products are
A) carbon monoxide and hydrogen
B) formaldehyde and water vapour
C) formic acid and water vapour
D) carbon monoxide and water vapour

130
CH 3  OH  O 2  H  CHO  H 2 O
Cu

Ans:
b) formaldehyde and water vapour

131
67). Which of these is not a product
of phenol?

A) bakelite B) phenolphthalein
C) paracetamol D) melamine

132
Ans:

D) Melamine

133
68).(a) di n-propyl ether is
manufactured by heating n-propyl
alcohol with conc. H2SO4.
(b) di isopropylether cannot be
obtained in the same way because
elimination takes place to give
alkenes.
A) A is true, B is wrong
B) A is wrong, B is true
C) both are true D)both are wrong
134
Ans: C) both are true
Because n-propyl alcohol is 1°
alcohol. Isopropyl alcohol is 2°
alcohol.

135
69). To get cresol, phenol is
subjected to

A) Wurtz reaction
B) Fittig reaction
C)Friedel-Crafts reaction
D)Gatterman reaction

136
Ans: C)Friedel-Craft’s reaction

137
70). C7H8O could be which of the
following?

i] cresol ii] benzyl alcohol

iii] anisole iv] toluidine

A) i, ii, iii B) ii, iii

C) ii, iii, iv D) i, ii, iv
138
C7H8O can be

Ans: a) i, ii, iii

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71). A compound ‘X’ with molecular formula
C3H8O can be oxidized to a compound
with molecular formula C3H6O2. ‘X’ is
most likely a/an

(A)primary alcohol
(B)secondary alcohol
(C) Aldehyde
(D) ketone

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Ans: (A)

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72).Which is not a phenol –

A) aspirin
B)salicylic acid
C) phenyl salicylate (salol)
D) naphthol

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is aspirin it is not a phenol.
Ans: A) Aspirin

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Wish you all the best

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