QUESTION BANK

CLASS XII (CHEMISTRY)

UNIT 5 : ALCOHOLS, PHENOLS & ETHERS
Q.NO MULTIPLE CHOICE QUESTIONS
1 Which of the following gives positive iodoform test?
(A) C6H5CH2CH2OH
(B)CH3CH(CH3)CH2OH
(C) PhCHOHCH3
(D) CH3CH2CH(OH) CH2CH3
2 What is the IUPAC name of the compound given below?
CH3 CH CH2 CH2 CH CH3

Cl OH

(A) 2-Chloro-5-hydroxyhexane
(B) 2-Hydroxy-5-chlorohexane
(C) 5-Chlorohexan-2-ol
(D) 2-Chlorohexan-5-ol
3 CH3CH2OH is converted into CH3CHO by ______________reagent.
(A) catalytic hydrogenation
(B) treatment with LiAlH4.
(C) treatment with pyridinium chlorochromate
(D) treatment with KMnO4
4 Find out the correct option in the increasing order of boiling point of following compounds:
Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol.
(A) Propan-1-ol, butan-2-ol, butan-1-ol, pentan-1-ol
(B) Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol
(C) Pentan-1-ol, butan-2-ol, butan-1-ol, propan-1-ol
(D) Pentan-1-ol, butan-1-ol, butan-2-ol, propan-1-ol
5 Lucas reagent is:
(A) anhydrousCaCl2 and conc. HCI
(B) anhydrous ZnCl2 and conc. HCI
(C) anhydrous AlCl3 and conc. HCI
(D) anhydrous PdCl2 and conc. HCI
6 What is the product (A) in the following reaction?
(i) B2H6
(A)
(ii) H2O2/OH-

(A) Pentan-1-ol
(B) 2-Methylbutan-1-ol
(C) 2-Metbylbutan-2-ol
(D) 3-Methylbutan-1-ol
7 Ethyl alcohol can be prepared from Grignard reagent by the reaction of :
(A) HCHO
(B) CH3CHO
(C) RCN
(D) RCOCI

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8 During the dehydration of alcohols to alkenes by heating with conc. H2SO4, the initiating step is:
(A) elimination of water
(B) protonation of an alcohol molecule
(C) formation of an ester
(D) formation of carbocation
Dehydration of alcohol to alkene by heating with conc. H2SO4 the initiation step is ____ followed
with _____ mechanism.
(A) Elimination of water, free radical
(B) Formation of an ester, free radical
(C) Protonation of alcohol, carbocation
(D) Protonation of alcohol, carbanion
9 Identify the secondary alcohols from the following set:
(i)CH3CH2CH(OH)CH3
(ii) (C2H5)3COH
OH

(iii)

HO CH3

(iv)

(A) (i) and (iv)

(B)(i) and (iii)
(C)(i) and (ii)
(D)(i), (iii) and (iv)
10 Phenol is less acidic than ______________.
(A) ethanol
(B) o-nitrophenol
(C) o-methylphenol
(D) o-methoxyphenol
11 When vapours of an alcohol are passed over heated reduced copper at 573K, alcohol is converted
into alkene, the alcohol is:
( A) tertiary
(B) primary
(C) secondary
(D) benzyl alcohol
12 A compound 'X' undergoes reduction with LiAlH4 to yield 'Y'. When vapours of 'Y' are passed
over freshly reduced copper at 573K, 'X' is formed. What is 'Y’?
(A) CH3COCH3
(B)CH3CHO
(C) CH3CH2OH
(D) CH3-O--CH3.
13 In the following sequence of reactions,

the compound D is:

(A) propanal
(B) butanal
(C) Butan-1-ol
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 (D)Propan-1-ol
14 Iodoform test is not given by
(A) Ethanol
(B) Ethanal
(C) Pentan-2-one
(D) Pentan-3-one
15 Which of the following compounds will react with sodium hydroxide solution in water?
(A) C6H5OH
(B) C6H5CH2OH
(C) (CH3)3 COH
(D) C2H5OH
16 In the following reaction,
Conc.H2SO4
C2 H5 OH Z ; dentify "Z"
443K

(A) CH2 = CH2

(B) CH3CH2OCH2CH3
(C) CH3CH2 –HSO4
(D) (CH3CH2 )2SO4
16 Phenol is more acidic than alcohol because
(a) phenol is more stable than water
(b) phenol is aromatic and alcohol is aliphatic
(c) phenoxide ion is resonance stabilised , alkoxide ion is unstable.
(d) None of these
17 Acidity of phenol is due to
(a) hydrogen bonding
(b) phenolic group
(c) benzene ring
(d) resonance stabilisation of its conjugate base.
18 Which one of the following compounds has the most acidic nature?

19 When phenol is treated with excess bromine water, it gives:

(a) m-Bromophenol
(b) o- and p-Bromophenol
(c) 2, 4-Dibromophenol
(d) 2, 4, 6-Tribromophenol
20 When phenol is heated with CHCl3 and alcoholic KOH when salicyladehyde is produced. This
reaction is known as

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 (a) Rosenmund’s reaction
(b) Reimer-Tiemann reaction
(c) Friedel-Crafts reaction
(d) Sommelet reaction
21 On distilling phenol with Zn dust, one gets :
(a) Toluene
(b) Benzaldehyde + ZnO
(c) ZnO + benzene
(d) Benzoic acid
22 Phenols do not react with one of the following :
(a) Alkali metals
(b) Sodium hydroxide
(c) Potassium hydroxide
(d) Sodium bi-carbonate
23 In the reaction

(a) benzaldehyde
(b) chlorobenzene
(c) benzoic acid
(d) salicylic acid
24 To distinguish between salicylic acid and phenol, one can use
(a) NaHCO3 solution
(b) 5% NaOH solution
(c) neutral FeCl3
(d) bromine water
25 Aspirin is an acetylation product of
(a) p-Dihydroxybenzene
(b) o-Hydroxybenzoic acid
(c) o-Dihydroxybenzene
(d) m-Hydroxybenzoic acid
26 Phenol is less acidic than_______________ .
(a) ethanol
(b) o–nitrophenol
(c) o-methylphenol
(d) o-methoxyphenol

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 27 Which of the following is most acidic?
(a) Benzyl alcohol
(b) Cyclohexanol
(c) Phenol (d) m-Chlorophenol
28 In the reaction

Phenol behaves as
(a) Bronsted base
(b) Bronsted acid
(c) Lewis acid
(d) Lewis base
29 Which one is formed when sodium phenoxide is heated with ethyl iodide ?
(a) Phenetole
(b) Ethyl phenyl alcohol
(c) Phenol
(d) None of these
30 Phenol when treated with neutral FeCl3 , it gives a complex of
a) violet colour
b) red colour
c) green colour
d) yellow colour

31. The IUPAC name of is

(a) 5-Ethylheptane-2,4-diol (b) 5-Methylheptane-2,4-diol

(c) 3-Methylheptane-4,6-diol (d) 2-Ethylhexane-4,6-diol

32. Which of the following are used to convert RCHO into RCH2OH?

(i) H2/Pd (ii) LiAlH4 (iii) NaBH4 (iv) Reaction with RMgX followed by hydrolysis

(a) (i) and (ii) (b) (i) ,(ii) and(iii)

(c) (ii),(iii) and(iv) (d) (i) and (iii)

33. Acid catalyzed hydration of alkene is an example of

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(a) free radical substitution (b) electrophilic substitution

(c) nucleophilic addition (d) electrophilic addition

34. A tertiary alcohol is obtained by the reaction of Grignard reagent with:

(a) Butanone (b) Propanone

(c) Acetone (d) All of the above

35. Which of the following has highest boiling point?

(a) CH3-CH2-CH2-CH2-OH (b)

(c) CH3-CH2-CH2-CH2-CH2OH (d)

36. Which of the following is correct?

(a) On reduction of any aldehyde, secondary alcohol is formed.

(b) Sucrose on reaction with NaCl gives invert sugar

(c) Reaction of vegetable oil with H2SO4 gives glycerine

(d) Alcoholic iodine gives iodoform with NaOH

37.

The product Y is

(a) Propan-2-ol (b) Propan-1-ol

(c) Acetaldehyde (d) 2-Methyl propan-1-ol

38. The main product of the following reaction is-

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39. Strongest acid among the following is-

(a) Pentan-2-ol (b) Butan-2-ol

(c) Butan-1-ol (d) 2-Methyl Propan-2-ol

40. The compound which reacts fastest with Lucas reagent at room temperature:

(a) 2-Methylpropan-1-ol (b) Butan-2-ol

(c) Butan-1-ol (d) 2-Methyl Propan-2-ol

41. Which of the following reagents cannot, be used to oxidise primary alcohols to aldehydes?

(a) CrO3 in anhydrous medium (b) KMnO4 in acidic medium

(c) Pyridinium chlorochromate (d) Heat in the presence of Cu at 573 K

42. Which of the following alcohols will give the most stable carbocation during dehydration?
(a) 2-methyl-1-propanol (b) 2-methyl-2-propanol
(c) 1-Butanol (d) 2-Butanol

43. Vapours of an alcohol X when passed over hot reduced copper, produce an alkene, the alcohol is
(a) primary alcohol (b) secondary alcohol
(c) tertiary alcohol (d) dihydric alcohol

44. The best reagent to convert pent-3-en-2-ol into pent-3-en- 2-one is

(a) acidic permanganate (b) acidic dichromate
(c) chromic anhydride in glacial acetic acid (d) pyridiriium chlorochromate

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45. During dehydration of alcohols to alkenes by heating with conc. H2SO4 the initial step is
(a) formation of an ester (b) protonation of alcohol molecule
(c) formation of carbocation (d) elimination of water

46. The Compound Obtained by the Reaction of Ethene with Diborane Followed by Hydrolysis with Alkaline
H2O2 is___

(a) Ethanol ` (b) propanol

(c) ethanal (d) triethyl bromide

47. In the following sequence of reactions, the end product (C) is

(a) acetone (b) methane

(c) acetaldehyde (d) ethyl alcohol

48. Vapours of an alcohol X when passed over hot reduced copper, produced an
alkene, the alcohol is
(a) primary alcohol (b) secondary alcohol
(c) tertiary alcohol (d) dihydric alcohol
49.Which of the following alcohols will give the most stable carbocation during
dehydration
(a) 2-Methyl-1-propanol (b)2-Methyl-2-propanol
(c) 1-Butanol (d) 2-Butanol
50. Boiling point of ethyl alcohol is greater than the hydrocarbon of comparable
molecular masses due to
(a) van der waals forces (b) London forces
(c) polarity (d) hydrogen bonding
51. The most suitable reagent for the conversion of RCH2OH RCHO
(a) K2Cr2O7 (b) CrO3 (c) KMnO4 (d) PCC
52. The total number of isomers possible for compound with molecular formula
C5H12O having -OH as functional is
(a) 8 (b) 6(c) 4 (d) 12
53. How many alcohols with molecular formula C4H10O are chiral in nature
(a) 1 (b) 2 (c) 3 (d) 4
54. Primary, secondary and tertiary alcohols can be distinguished by
(a)Borsche’s test (b)Lucas test
(c) Hinsberg’stest (d)Tollen’s test
55. During dehydration of alcohols to alkenes by heating with conc. H2SO4, the
initial step is
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(a) formation of an ester (b) protonation of alcohol molecule
(c) formation of carbocation(d) elimination of water
56. From amongst the following alcohols the one that would react fastest with
conc. HCl and anhydrous ZnCl2, is
(a) 2-Methylpropanol (b) 1-Butanol
(c) 2-Butanol (d) 2-Methylpropan-2-ol
57. An unknown alcohol is treated with the “Lucas reagent” to determine
whether the alcohol is primary, secondary and tertiary. Which alcohol
reacts fastest and by what mechanism
(a) tertiary alcohol by SN2(b)secondary alcohol by SN1
(c) tertiary alcohol by SN1 (d)secondary alcohol by SN2
58. What happens when tertiary butyl alcohol is passed over heated copper at
300oC
(a) secondary butyl alcohol is formed (b)2-methylpropene is formed
(c) 1-butene is formed(d) butanol is formed

59. Propanone on reaction with alkyl magnesium bromide followed by

hydrolysis will produce
(a) primary alcohol(b) secondary alcohol
(c) tertiary alcohol(d) carboxylic acid
60. By which of the following methods alcohol can be prepared in excellent yield
(a) from alkenes(b) by hydroboration-oxidation
(c) from carbonyl compounds (d) from Grignard reagent
61. Lucas reagent is
(a) conc. HCl and anhydrous ZnCl2(b)conc. HNO3 and hydrous ZnCl2
(c) conc. HCl and hydrous ZnCl2 (d)conc. HNO3 andanhydrous ZnCl2
62. Acid catelysed hydration of alkene is an example of
(a) free radical substitution (b)nucleophilic substitution
(c) nuclephilic addition (d) electrophilic addition

63 The reagent used for the oxidation of primary alcohol to aldehyde is-
(i)CrO3 in anhydrous medium
(ii)PCC
(iii)both a and b
(ib) acidified KMnO4
64 Methanol is known as –
(i) Coal tar
(ii) Wood spirit

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 (iii) Ethyl alcohol
(iv) both (i) and (ii)
65 By dehydration of ethyl alcohol __________ formed
(i)ethene
(ii)ethyne
(iii)propane
(iv)butene
66 In step (II ) of dehydration of alcohols _____________ is formed.
(i) Carbocation
(ii) Carbanion
(iii) both Carbocation and Carbanion
(iv)None of these
67 Which reagent is used for dehydration of alcohols?
(i) Concentrated sulphuric acid
(ii) HI
(ii)HF
(iv) HC
68 The IUPAC name of ethyl alcohol is-.
(i)Methanol
(ii)Ethanol
(iii) Methylated spirit
(iv) Wood spirit
69 The IUPAC name of CH3-CH(OH)-CH2-CH3 is –
(i)Butan-2-ol
(ii)Butan-3 -ol
(iii) Buatne-1 -ol
(iv)Buatan-4-ol
70 Alcohols have more boiling than alkanes because
(i) Alcohols are soluble in water
(ii) Alcohols have H bonding between their molecules but alkanes do not have H bonding.
(iii)Both (i) and ( ii) are correct.
(iv) None of these

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71 CH3-CH2-OH is a –
(i) Primary alcohol
(ii) Secondary alcohol
(iii) Tertiary alcohol
(iv) None of the above
72 In allylic alcohols -OH is attached to ___________ next to the carbon -carbon double bond.
(i)sp2 hybridised Carbon
(ii)sp hybridised Carbon
(iii)sp3 hybridised Carbon
(iv)sp3d hybridised Carbon
73 In vinylic alcohols -OH is bonded to
(i)sp2 hybridised Carbon
(ii)sp hybridised Carbon
(iii)sp3 hybridised Carbon
(iv)sp3d hybridised Carbon
74 Solubility of alcohols in water is due to it’s ability to form ________ bonds with water.
(i) Hydrogen
(ii) Carbon
(iii)Nitrogen
(iv) Oxygen
75 Alcohols have more boiling point than ethers because they have ________ H bonding in
between the molecules -
(i) Intermolecular
(ii) Intramolecular
(iii) Both (i) and (ii)
(iv) None of these
76 Out of pentan-1-ol and ethanol which will have higher boiling point-
(i)Ethanol
(ii) pentan-1-ol
(iii) Both (i) and (ii)
(iv) None of these
77 When the bond between O-H is broken then alcohols behave as

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 (i) Nucleophiles
(ii) Electrophiles
(iii) Can behave both as Electrophiles and Nucleophiles
(iv) None of the above

78 In the reaction of phenol with CHCl3 and aqueous NaOH at 343 K, the electrophile attacking the
ring is:

(A) CHCl3

(B) +CHCl2

(C) :CCl2

(D) COCl2

79 Select the incorrect statement

(A) Phenol is acidic due to polar nature of -OH group

(B) An electron withdrawing group increases the electron density on oxygen

(C) An electron releasing group increases the electron density on oxygen

(D) Alcohols are less acidic than phenol.

80 Phenol is least reactive for aromatic nucleophilic substitution because:

(A) Carbon–oxygen bond has some double bond character due to resonance.

(B) Oxygen is present in sp hybrid carbon which makes carbon–oxygen bond

stronger.

(C) Oxygen is highly electronegative which decreases bond length between

carbon and oxygen.

(D) All are correct.

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81 Which is most acidic?

(A) Salicylic acid

(B) 4-nitrophenol

(C) Cresol

(D)2-nitrophenol

82 When we prepare phenol from cumene, then by-product of the reaction is

(A) Acetaldehyde

(B) Acetone

(C) Benzene

(D) Dimethyl ether

83 Phenol can be distinguished from alcohol by which reagent :

(A) Na

(B) NaOH

(C) Br2 /HOH

(D) Alcoholic FeCI3

84 tert–Butyl methyl ether on heating with HI gives a mixture of

(A) tert–Butyl alcohol and methyl iodide

(B) tert–Butyl iodide and methanol

(C) Isobutylene and methyl iodide

(D) Isobutylene and methanol

85 Phenol does not undergo nucleophilic substitution reaction easily due to:

(A) acidic nature of phenol

(B) partial double bond character of C-OH bond

(C) partial double bond character of C-O bond

(D) instability of phenoxide ion

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86 An ether is more volatile than alcohol having the same molecular formula. This

is due to

(A) intermolecular hydrogen bonding in alcohols.

(B) dipolar character of ethers
(C) alcohols, having resonance structures
(D) intermolecular hydrogen bonding in ethers

87 Which of the following cannot be made by using Williamson Synthesis:

(A) Methoxybenzene

(B) Benzyl p-nitrophenyl ether

(C) tert. butyl methyl ether

(D) Ditert. butyl ether

88 Conversion of phenol to salicyclic acid and to salicyaldehyde are known as

(A) Reimer-Tiemann reaction and Kolbe’s reaction

(B) Williamson’s synthesis and Hydrobration-oxidation

(C) Kolbe’s reaction and Williamson’s synthesis

(D) Kolbe’s reaction and Reimer-Tiemann reaction

89 The I.U.P.A.C. name of the ether CH2 = CH-CH2-O- CH3 is

(A) Alkyl methyl ether

(B) l-Methoxy-2-propene

(C) 3-Methoxy-l-propene

(D) Vinyl dimethyl ether

90 The major product obtained on heating excess of ethanol with Conc.H2SO4 at 413K is

(A) CH2=CH2

(B) (C2H5)2O

(C) But-2-ene

(D) (CH3CH2)2SO4

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91 Aspirin is obtained by acetylation of

(A) o-hydroxy benzoic acid

(B) m-hydroxy benzoic acid

(C) o-dihydroxy benzene

(D) p-dihydroxy benzene

92 Identify Y in the following reaction sequence

(A) Benzene

(B) Benzaldehyde

(C) Phenol

(D) None of these

93.Sodium salt of benzene sulphonic acid on fusion with caustic soda gives
(a) Benzene
(b) Phenol
(c) Thiophenol
(d) Benzoic acid
94. In the following compounds:
OH
OH
OH
OH

NO2

III NO2 IV
CH3 II
I
The order of acidity is
(a) III > IV > I > II
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21 P
Page 15 of 21
(b) I > IV > III > II
(c) II > I > III > IV
(d) IV > III > I > II

95. Dehydration of alcohol to ethers is catalysed by

(a) cone. H2SO4 at 413 K
(b) Hot NaOH
(c) Hot HBr
(d) Hot HNO3

96.An ether is more volatile than alcohol having the same molecular formula. This is due to
(a) intermolecular hydrogen bonding in alcohols.
(b) dipolar character of ethers
(c) alcohols, having resonance structures
(d) intermolecular hydrogen bonding in ethers.

97.When Phenol is distilled with zinc dust, it gives

(a) Benzene
(b) Toluene
(c) Benzaldehyde
(d) Benzoic acid

98.In the reaction of phenol with CHCl3 and aqueous NaOH at 343 K, the electrophile attacking the ring is:
(a) CHCl3
(b) CHCl2
(c) CCl2
(d) COCl2
99.Phenol reacts with Br2 in CS2 at low temperature to give
(a) o-Bromophenol
(b) o-and p-bromophenols
(c) p-Bromophenol
(d) 2, 4, 6Tribromophenol

100. In the following reaction

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(a) ethane
(b) ethylene
(c) butane
(d) propane
101.The I.U.P.A.C. name of the ether CH2 = CH-CH2O CH3 is
(a) Alkyl methyl ether
(b) l-Methoxy-2-propene
(c) 3-Methoxy-l-propene
(d) Vinyl dimethyl ether
102. Ethers are
(a) Neutral
(b) Basic
(c) Acidic
(d) Amphoteric
103.Phenol when treated with excess of bromine water gives a white precipitate of
(a) 2, 4, 6-tribromophenol
(b) o-bromophenol
(c) p-bromophenol
(d) bromobenzene
104.Ortho-nitrophenol is less soluble in water than, p- and m- nitrophenols because
(a) o-nitrophenol shows intramolecular H-bonding
(b) o-nitrophenol shows intermolecular H-bonding
(c) melting point of o-nitrophenol is lower than those of m- and p-isomers
(d) o-nitrophenol is more volatile in steam than those of m- and p-isomers
105. Identify the final product of the reaction sequence.

(a) Benzophenone
(b) Acetophenone
(c) Diphenyl
(d) Methyl salicylate

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106.Conversion of phenol to salicyclic acid and to salicyaldehyde are known as (respectively)
(a) Reimer-Tiemann reaction and Kolbe’s reaction
(b) Williamson’s synthesis and Hydrobration-oxidation
(c) Kolbe’s reaction and Williamson’s synthesis
(d) Kolbe’s reaction and Reimer-Tiemann reaction
107.Which of the following is phenol?
(a) Cresol
(b) Catechol
(c)Benzenol
(d) All of these

KEY/ANSWER SHEET
Multiple-choice question
Q.No.1 Answer-C
Q.No.2 Answer-C
Q.No.3 Answer-C
Q.No.4 Answer-A
Q.No.5 Answer-B
Q.No.6 Answer-A
Q.No.7 Answer-A
Q.No.8 Answer-B
Q.No.9 Answer-A
Q.No.10 Answer-B
Q.No.11 Answer-A
Q.No.12 Answer-C
Q.No.13 Answer-D
Q.No.14 Answer-D
Q.No.15 Answer-A
Q.No.16 Answer-A
17 c
18 d
19 b
20 d
21 b
22 c
23 d
24 d
25 c
26 b

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27 b
28 d
29 b
30 a
31 (b) 5-Methylheptane-2,4-diol
32 (b) (i) ,(ii) and(iii)
33 (d) electrophilic addition
34 (d) All of the above
35 (c) CH3-CH2-CH2-CH2-CH2OH
36 (d) Alcoholic iodine gives iodoform with NaOH
37 (a) Propan-2-ol
38

39 9. (c) Butan-1-ol
40 10. (d) 2-Methyl Propan-2-ol
41 11. (b) KMnO4 in acidic medium
42 12. (b) 2-methyl-2-propanol
43 13. (c) tertiary alcohol
44 14. (d) pyridiriium chlorochromate
45 15. (b) protonation of alcohol molecule
46 ethanol
47 17. (d) ethyl alcohol
48 C
49 B
50 D
51 D
52 A
53 A
54 B
55 B
56 D
57 C
58 B
59 C
60 B
61 A
62 D

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63 (III)
64 (II)
65 (I)
66 (I)
67 (I)
68 (II)
69 (I)
70 (II)
71 (I)
72 (III)
73 (I)
74 (I)
75 (I)
76 (II)
77 (I)
78 C
79 B
80 A
81 A
82 B
83 D
84 B
85 C
86 A
87 D
88 D
89 C
90 B
91 A
92 B
93 b phenol
94 d.iv>iii>i>ii
95 with coc H2SO4 at 413K
96 a.intermolecular hydrogen bonds in alcohols
97 a.benzene
98 c.CCl2
99 b.o- and p-bromophenols
100 a.ethane
101 c.3-methoxy -1-propene
102 b.basic
103 a.2,4,6 tribromophenol

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104 a.o-nitrophenol shows intramolecular hydrogen bonding
105 b.acetophenone
107 d kolbe’s reaction and Reimer tiemann reaction
107 d.all of these

The questions submitted by the PGTs (Chemistry) of KVs of Bhubaneswar, Guwahati, Kolkata, Ranchi,
Silchar and Tinsukia Regions.
Vetted by: Tinsukia Region

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