Unit

11
ALCOHOLS, PHENOLS
AND ETHERS

I. Multiple Choice Questions (Type-I)

1. Monochlorination of toluene in sunlight followed by hydrolysis with aq. NaOH
yields.
(i) o-Cresol
(ii) m-Cresol
(iii) 2, 4-Dihydroxytoluene
(iv) Benzyl alcohol
2. How many alcohols with molecular formula C4H10O are chiral in nature?
(i) 1
(ii) 2
(iii) 3
(iv) 4
3. What is the correct order of reactivity of alcohols in the following reaction?

ZnCl
R—OH + HCl ⎯⎯⎯⎯
2
→ R—Cl + H2O
(i) 1° > 2° > 3°
(ii) 1° < 2° > 3°
(iii) 3° > 2° > 1°
(iv) 3° > 1° > 2°
4. CH3CH2OH can be converted into CH3CHO by ______________.
(i) catalytic hydrogenation
(ii) treatment with LiAlH4

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 (iii) treatment with pyridinium chlorochromate
(iv) treatment with KMnO4

5. The process of converting alkyl halides into alcohols involves_____________.

(i) addition reaction
(ii) substitution reaction
(iii) dehydrohalogenation reaction
(iv) rearrangement reaction

6. Which of the following compounds is aromatic alcohol?

(i) A, B, C, D
(ii) A, D
(iii) B, C
(iv) A

7. Give IUPAC name of the compound given below.

(i) 2-Chloro-5-hydroxyhexane
(ii) 2-Hydroxy-5-chlorohexane
(iii) 5-Chlorohexan-2-ol
(iv) 2-Chlorohexan-5-ol

8. IUPAC name of m-cresol is ___________.

(i) 3-methylphenol
(ii) 3-chlorophenol
(iii) 3-methoxyphenol
(iv) benzene-1,3-diol

9. IUPAC name of the compound is ______________.

(i) 1-methoxy-1-methylethane
(ii) 2-methoxy-2-methylethane

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 (iii) 2-methoxypropane
(iv) isopropylmethyl ether

10. Which of the following species can act as the strongest base?
V
(i) OH
V
(ii) OR
V
(iii) O C6H5

(iv)

11. Which of the following compounds will react with sodium hydroxide solution
in water?
(i) C6H5OH
(ii) C6H5CH2OH
(iii) (CH3)3 COH
(iv) C2H5OH

12. Phenol is less acidic than ______________.

(i) ethanol
(ii) o-nitrophenol
(iii) o-methylphenol
(iv) o-methoxyphenol

13. Which of the following is most acidic?

(i) Benzyl alcohol
(ii) Cyclohexanol
(iii) Phenol
(iv) m-Chlorophenol

14. Mark the correct order of decreasing acid strength of the following compounds.

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 (i) e>d>b>a>c
(ii) b>d>a>c>e
(iii) d>e>c>b>a
(iv) e>d>c>b>a
15. Mark the correct increasing order of reactivity of the following compounds
with HBr/HCl.

(i) a<b<c
(ii) b<a<c
(iii) b<c<a
(iv) c<b<a
16. Arrange the following compounds in increasing order of boiling point.
Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol
(i) Propan-1-ol, butan-2-ol, butan-1-ol, pentan-1-ol
(ii) Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol
(iii) Pentan-1-ol, butan-2-ol, butan-1-ol, propan-1-ol
(iv) Pentan-1-ol, butan-1-ol, butan-2-ol, propan-1-ol

II. Multiple Choice Questions (Type-II)

Note : In the following questions two or more options may be correct.
17. 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

18. Which of the following reactions will yield phenol?

(i)

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 (ii)

(iii)

(iv)

19. Which of the following reagents can be used to oxidise primary alcohols to
aldehydes?
(i) CrO3 in anhydrous medium.
(ii) KMnO4 in acidic medium.
(iii) Pyridinium chlorochromate.
(iv) Heat in the presence of Cu at 573K.
20. Phenol can be distinguished from ethanol by the reactions with _________.
(i) Br2/water
(ii) Na
(iii) Neutral FeCl3
(iv) All the above

21. Which of the following are benzylic alcohols?

(i) C6H5—CH2—CH2OH
(ii) C6H5—CH2OH
(iii)

(iv)

III. Short Answer Type

22. What is the structure and IUPAC name of glycerol?

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23. Write the IUPAC name of the following compounds.

(A) (B)

24. Write the IUPAC name of the compound given below.

25. Name the factors responsible for the solubility of alcohols in water.
26. What is denatured alcohol?
27. Suggest a reagent for the following conversion.

28. Out of 2-chloroethanol and ethanol which is more acidic and why?
29. Suggest a reagent for conversion of ethanol to ethanal.
30. Suggest a reagent for conversion of ethanol to ethanoic acid.
31. Out of o-nitrophenol and p-nitrophenol, which is more volatile? Explain.
32. Out of o-nitrophenol and o-cresol which is more acidic?
33. When phenol is treated with bromine water, white precipitate is obtained. Give
the structure and the name of the compound formed.
34. Arrange the following compounds in increasing order of acidity and give a
suitable explanation.
Phenol, o-nitrophenol, o-cresol
35. Alcohols react with active metals e.g. Na, K etc. to give corresponding alkoxides.
Write down the decreasing order of reactivity of sodium metal towards primary,
secondary and tertiary alcohols.
36. What happens when benzene diazonium chloride is heated with water?
37. Arrange the following compounds in decreasing order of acidity.
H2O, ROH, HC ≡ CH
38. Name the enzymes and write the reactions involved in the preparation of ethanol
from sucrose by fermentation.
39. How can propan-2-one be converted into tert- butyl alcohol?
40. Write the structures of the isomers of alcohols with molecular formula C4H10O.
Which of these exhibits optical activity?

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 41. Explain why is OH group in phenols more strongly held as compared to OH
group in alcohols.
42. Explain why nucleophilic substitution reactions are not very common in phenols.
43. Preparation of alcohols from alkenes involves the electrophilic attack on alkene
carbon atom. Explain its mechanism.
44. Explain why is O==C==O nonpolar while R—O—R is polar.
45. Why is the reactivity of all the three classes of alcohols with conc. HCl and
ZnCl2 (Lucas reagent) different?
46. Write steps to carry out the conversion of phenol to aspirin.
47. Nitration is an example of aromatic electrophilic substitution and its rate
depends upon the group already present in the benzene ring. Out of benzene
and phenol, which one is more easily nitrated and why?
48. In Kolbe’s reaction, instead of phenol, phenoxide ion is treated with carbon
dioxide. Why?
49. Dipole moment of phenol is smaller than that of methanol. Why?
50. Ethers can be prepared by Williamson synthesis in which an alkyl halide is
reacted with sodium alkoxide. Di-tert-butyl ether can’t be prepared by this
method. Explain.
51. Why is the C—O—H bond angle in alcohols slightly less than the tetrahedral
angle whereas the C—O—C bond angle in ether is slightly greater?
52. Explain why low molecular mass alcohols are soluble in water.
53. Explain why p-nitrophenol is more acidic than phenol.
54. Explain why alcohols and ethers of comparable molecular mass have different
boiling points?
55. The carbon-oxygen bond in phenol is slightly stronger than that in methanol.
Why?
56. Arrange water, ethanol and phenol in increasing order of acidity and give
reason for your answer.

IV. Matching Type

Note : Match the items of Column I and Column II in the following questions.
57. Match the structures of the compounds given in Column I with the name of
the compounds given in Column II.

Column I Column II

(i) (a) Hydroquinone

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 (ii) (b) Phenetole

(iii) (c) Catechol

(iv) (d) o-Cresol

(v) (e) Quinone

(vi) (f) Resorcinol

(g) Anisole

58. Match the starting materials given in Column I with the products formed by
these (Column II) in the reaction with HI.

Column I Column II

(i) CH3—O—CH3 (a)

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 (ii) (b)

(iii) (c)

(iv) (d) CH3—OH + CH3—I

(e)

(f)

(g)

59. Match the items of column I with items of column II.

Column I Column II
(i) Antifreeze used in car engine (a) Neutral ferric chloride
(ii) Solvent used in perfumes (b) Glycerol
(iii) Starting material for picric acid (c) Methanol
(iv) Wood spirit (d) Phenol
(v) Reagent used for detection of (e) Ethleneglycol
phenolic group
(vi) By product of soap industry (f) Ethanol
used in cosmetics
60. Match the items of column I with items of column II.

Column I Column II
(i) Methanol (a) Conversion of phenol to
o-hydroxysalicylic acid
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 (ii) Kolbe’s reaction (b) Ethyl alcohol
(iii) Williamson’s synthesis (c) Conversion of phenol to
salicylaldehyde
(iv) Conversion of 2° alcohol to ketone (d) Wood spirit
(v) Reimer-Tiemann reaction (e) Heated copper at 573K
(vi) Fermentation (f) Reaction of alkyl halide with
sodium alkoxide

V. Assertion and Reason Type

Note : In the following questions a statement of assertion followed by a
statement of reason is given. Choose the correct answer out of the following
choices.
(i) Assertion and reason both are correct and reason is correct explanation
of assertion.
(ii) Assertion and reason both are wrong statements.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion is wrong statement but reason is correct statement.
(v) Both assertion and reason are correct statements but reason is not correct
explanation of assertion.
61. Assertion : Addition reaction of water to but-1-ene in acidic medium
yields butan-1-ol
Reason : Addition of water in acidic medium proceeds through the
formation of primary carbocation.
62. Assertion : p-nitrophenol is more acidic than phenol.
Reason : Nitro group helps in the stabilisation of the phenoxide ion by
dispersal of negative charge due to resonance.
63. Assertion : IUPAC name of the compound

is 2-Ethoxy-2-methylethane.

Reason : In IUPAC nomenclature, ether is regarded as hydrocarbon

derivative in which a hydrogen atom is replaced by —OR or
—OAr group [where R = alkyl group and Ar = aryl group]
64. Assertion : Bond angle in ethers is slightly less than the tetrahedral angle.
Reason : There is a repulsion between the two bulky (—R) groups.
65. Assertion : Boiling points of alcohols and ethers are high.
Reason : They can form intermolecular hydrogen-bonding.

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 66. Assertion : Like bromination of benzene, bromination of phenol is also
carried out in the presence of Lewis acid.
Reason : Lewis acid polarises the bromine molecule.
67. Assertion : o-Nitrophenol is less soluble in water than the m- and
p-isomers.
Reason : m- and p- Nitrophenols exist as associated molecules.
68. Assertion : Ethanol is a weaker acid than phenol.
Reason : Sodium ethoxide may be prepared by the reaction of ethanol
with aqueous NaOH.
69. Assertion : Phenol forms 2, 4, 6 – tribromophenol on treatment with Br2
in carbon disulphide at 273K.
Reason : Bromine polarises in carbon disulphide.
70. Assertion : Phenols give o- and p-nitrophenol on nitration with conc.
HNO3 and H2SO4 mixture.
Reason : —OH group in phenol is o–, p– directing.

VI. Long Answer Type

71. Write the mechanism of the reaction of HI with methoxybenzene.

72. (a) Name the starting material used in the industrial preparation of phenol.
(b) Write complete reaction for the bromination of phenol in aqueous and
non aqueous medium.
(c) Explain why Lewis acid is not required in bromination of phenol?
73. How can phenol be converted to aspirin?
74. Explain a process in which a biocatalyst is used in industrial preparation of a
compound known to you.

Exemplar Problems, Chemistry 164

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