Alcohols, Phenols and Ethers 1

Previous Years’ CBSE

PREVIOUS Board
YEARS MCQS Questions

11.1 Classification 9. Draw the structure of hex-1-en-3-ol

compound. (Delhi 2012)
SA II (3 marks) 10. Write the IUPAC name of the following :
1. Classify the following as primary, secondary CH3
and tertiary alcohols : CH3 C C CH2OH
Br (AI 2012C)
(i)
11. Give the structure and IUPAC name of the
product formed when propanone is reacted
(ii) H2C CH—CH2OH
with methylmagnesium bromide followed by
(iii) CH3—CH2—CH2—OH (AI 2009)
hydrolysis. (AI 2012C)
11.2 Nomenclature 12. Write the structure of the molecule of compound
whose IUPAC name is 1-Phenylpropan-2-o1
VSA (1 mark) (AI 2010)
2. Write the IUPAC name of the given 13. Give the IUPAC name of the following
compound. compound :
H2C CH CH CH2 CH2 CH3
(AI 2009)
(AI 2016) OH
14. Write the structure of the following compound :
3. Write the IUPAC name of the given compound :
2-Methyl-2-ethoxypentane. (Delhi 2009C)
15. Write the IUPAC name of the following
compound :
(Delhi 2015)
4. Write the IUPAC name of the given compound : (AI 2008)
11.3 Structures of Functional Groups
(AI 2015)
VSA (1 mark)
5. Write the IUPAC name of the given
compound: 16. The C O bond is much shorter in phenol than
in ethanol. Give reason. (Delhi 2012C)
(Foreign 2015) 11.4 Alcohols and Phenols
6. Name the following according to IUPAC
system : VSA (1 mark)
CH3 CH CH2 CH3
17. Write the equation involved in the acetylation
OH (1/2, Delhi 2015C) of Salicylic acid. (Delhi 2015)
7. Write IUPAC name of the following compound : 18. Give reason for the following :
HO CH2 CH CH2 OH (Foreign 2014) Phenol is more acidic than ethanol.
OH (1/3, AI 2015)
8. Draw the structural formula of 19. Which of the following isomers is more volatile :
2-Methylpropan-2-ol molecule. (Delhi 2012) o-nitrophenol or p-nitrophenol? (Delhi 2014)
2

20. Write the equation involved in the following 38. Why do phenols not give the protonation
reaction : reaction readily? (1/3, AI 2008)
Reimer –Tiemann reaction (1/2, AI 2014, 2013) 39. How would you account for the following :
21. Write the equation involved in the following Phenols are much more acidic than alcohols.
reaction : (1/2, Delhi 2007)
Kolbe’s reaction (1/2, Delhi 2014C, 2013C)
22. How is toluene obtained from phenol? SA I (2 marks)

(1/3, Delhi 2013C) 40. Write the main product(s) in each of the
following reactions :
23. Give a chemical test to distinguish between
2-Pentanol and 3-Pentanol. (1/2, Delhi 2013C) (i) CH3 CH CH2
24. Of the two hydroxy organic compounds ROH
and R′OH, the first one is basic and other is (ii) C6H5 OH (Delhi 2016)
acidic in behaviour. How is R different from
R′? (Delhi 2013C) 41. Write the final product(s) in each of the
following reactions :
25. How would you obtain ethane-1, 2-diol from Cu/573 K
(i) CH3CH2 CH CH3
ethanol ? (AI 2013C)
26. How would you obtain acetophenone from OH
phenol? (AI 2013C) (i) CHCl3 + aq. NaOH
(ii) C6H5 OH (ii) H+
27. Ortho-nitrophenol has lower boiling point than (Delhi 2016)
p-nitrophenol. Why? (Delhi 2012C)
42. Explain the mechanism of dehydration steps of
28. Give a chemical test to distinguish between ethanol :
Benzoic acid and Phenol. (Delhi 2012C)
CH3CH2OH CH2 CH2+H2O
29. Illustrate the following name reaction
Reimer-Tiemann Reaction. (Delhi 2012C) (Delhi 2015C)
30. Give a chemical test to distinguish between 43. How are the following conversions carried
2-propanol and 2-methyl-2-propanol. out?
(i) Propene to propane-2-ol
(Delhi 2012C)
(ii) Benzyl chloride to Benzyl alcohol
31. Ortho-nitrophenol is more acidic than ortho- (2/3, Delhi 2015C)
methoxyphenol. Why? (1/2, Delhi 2012C)
44. Write the mechanism of acid dehydration of
32. Explain the following giving one example : ethanol to yield ethene. (AI 2015C)
Reimer-Tiemann reaction.
45. Write the mechanism of the following reaction :
(1/3, Delhi 2011, 2010, AI 2009C)
33. How would you convert ethanol to ethene? CH3CH2OH CH3CH2Br + H2O
(AI 2014, 2/3 Foreign 2014)
(AI 2011)
46. Name the reagents used in the following
34. Illustrate the following reaction giving a
reactions :
chemical equation : (i) Bromination of phenol to 2, 4, 6-tribro-
Kolbe’s reaction (Delhi 2010) mophenol
35. Give one chemical test to distinguish between (ii) Butan-2-one to Butan-2-o1
the following pairs of compounds. (iii) Friedel–Crafts alkylation of anisole
1-Propanol and 2-Propanol. (1/2, Delhi 2009C) (iv) Oxidation of primary alcohol to carboxylic
36. Describe the following with an example : acid (Foreign 2014)
Kolbe’s reaction (AI 2009C) 47. Name the different reagents needed to perform
37. Give reasons for the following : the following reactions :
(i) Phenol to Benzene
Propanol has higher boiling point than that of
the hydrocarbon butane. (AI 2009C) (ii) Dehydration of propan-2-ol to propene
Alcohols, Phenols and Ethers 3

(iii) Friedel-Crafts alkylation of anisole 58. How would you obtain the following :
(iv) Dehydrogenation of ethanol to ethanal (i) Benzoquinone from phenol
(Foreign 2014) (ii) 2-Methylpropan-2-ol from methyl
48. How are the following conversions carried magnesium bromide
out? (iii) Propan-2-ol from propene? (AI 2011)
(i) Propene to Propan-2-ol 59. Give the names of the reagents of bringing
(ii) Ethyl chloride to Ethanal (Delhi 2014C) about the following transformations :
49. Explain the following with an example for each : (i) Hexan-1-ol to hexanal
(i) Kolbe’s reaction (ii) But-2-ene to ethanol (Delhi 2011C)
(ii) Reimer-Tiemann reaction (2/3, AI 2014C) 60. Account for the following :
50. How will you convert : (i) Propanol has higher boiling point than
(i) Propene to propan-2-ol? butane.
(ii) Phenol to 2,4,6-trinitrophenol? (ii) Ortho-nitrophenol is more acidic than
(Delhi 2013) ortho-methoxyphenol. (2/3, Delhi 2011C)
51. How will you convert the following : 61. Account for the following :
(i) Propan-2-ol to propanone. (i) The boiling point of ethanol is higher than
(ii) Phenol to 2,4,6-tribromophenol. that of methanol.
(Delhi 2013) (ii) Phenol is a stronger acid than an alcohol.
52. Explain the mechanism of the following (Delhi 2011C)
reaction : 62. Write Reimer–Tiemann reaction giving an
H+ example. (AI 2011C)
CH3—CH2—OH → CH2 CH2 + H2O
443 K
(AI 2013) 63. How are the following conversions carried
out?
53. Explain the mechanism of acid catalysed
(i) Benzyl chloride to benzyl alcohol.
hydration of an alkene to form corresponding
(ii) Methyl magnesium bromide to 2-methyl-
alcohol. (AI 2012)
propan-2-ol. (Delhi 2010)
54. Explain the following behaviours :
64. Describe the mechanism of hydration of ethene
(i) Alcohols are more soluble in water than
to yield ethanol. (AI 2010C)
the hydrocarbons of comparable molecular
masses. 65. Describe a chemical test each to distinguish
(ii) Ortho-nitrophenol is more acidic than between the following pairs :
ortho-methoxyphenol. (AI 2012) (i) Ethanol and Phenol
55. Give a separate chemical test to distinguish (ii) 1-Propanol and 2-Propanol
between the following pairs of compounds : (Delhi 2008C, AI 2008)
(i) Ethanol and Phenol
SA II (3 marks)
(ii) 2-Pentanol and 3-Pentanol (Delhi 2012C)
66. How do you convert the following?
56. How would you obtain the following :
(i) Phenol to anisole
(i) 2-methylpentan-2-ol from 2-methyl-1-
pentene (ii) Propan-2-ol to 2-methylpropan-2-ol
(ii) Acetophenone from phenol (2/3, AI 2012C) (iii) Aniline to phenol (Delhi 2015)
57. How would you obtain 67. Predict the products of the following reactions :
(i) Picric acid (2, 4, 6-trinitrophenol) from (i) CH3—CH CH2 ?
phenol.
(ii) 2-Methylpropene from 2-methylpropanol? (ii) C6H5OH ?
(Delhi 2011) (iii) CH3CH2OH ? (Foreign 2015)
4

68. How are the following conversions carried out? (iii) Acid catalysed hydration of an alkene
(i) Benzyl chloride to benzyl alcohol forming an alcohol. (Delhi 2009)
(ii) Ethyl magnesium chloride to Propan-1-ol 77. Name the reagents which are used in the
(iii) Propene to Propan-2-ol. following conversions :
(AI 2015C, 2014C) (i) A primary alcohol to an aldehyde
69. (a) Write the mechanism of the following (ii) Butan-2-one to butan-2-ol
reaction : (iii) Phenol to 2, 4, 6-tribromophenol
CH3CH2OH CH3CH2Br + H2O (Delhi 2008)
(b) Write the equation involved in Reimer– 78. (a) Write the IUPAC name of the following :
Tiemann reaction. (Delhi 2014)
70. (a) Give chemical tests to distinguish between
the following pairs of compounds :
(i) Pentan-2-ol and Pentan-3-ol
(ii) Methanol and Phenol
(b) o-nitro phenol is more acidic than (b) Give reasons for the following :
o-methoxy phenol. Explain why. (i) Phenol is a stronger acid than alcohol.
(AI 2013C) (ii) Alcohols are comparatively more soluble
in water than the corresponding hydrocar-
71. Draw the structure and name of the product bons. (AI 2008C)
formed if the following alcohols are oxidized.
Assume that an excess of oxidising agent is 11.5 Some Commercially Important
used.
(i) CH3CH2CH2CH2OH Alcohols
(ii) 2-butenol
(iii) 2-methyl-1-propanol (Delhi 2012)
VSA (1 mark)

72. (a) Describe the mechanism of hydration of 79. Name a substance that can be used as an
ethene to yield ethanol. antiseptic as well as a disinfectant.
(b) Write Kolbe’s reaction with an example. (Delhi 2008)
(AI 2011C)
11.6 Ethers
73. Acid catalysed dehydration of t-butanol is faster
than that of n-butanol. Explain. (AI 2011C) VSA (1 mark)
74. How would you convert the following : 80. Write the main product(s) in the following
(i) Phenol to benzoquinone reaction :
(ii) Propanone to 2-methylpropan-2-ol
(iii) Propene to propan-2-o1. (AI 2010)
75. (i) Describe the mechanism of acid
dehydration of ethanol to yield ethene.
(ii) Describe a chemical test to distinguish (1/3, Delhi 2016, 1/2, AI 2016)
between ethanol and phenol. 81. How is the following conversion carried out?
(Delhi 2010C) Anisole to p-bromoanisole (1/3, Delhi 2015C)
76. Explain the mechanism of the following 82. Write the equations involved in the following
reactions : reaction :
(i) Addition of Grignard’s reagent to the Williamson synthesis
carbonyl group of a compound forming an (1/2, AI 2014, 2013, 1/2, Delhi 2014C)
adduct followed by hydrolysis. 83. Explain the following with an example :
(ii) Acid catalysed dehydration of an alcohol Williamson ether synthesis.
forming an alkene. (1/3, AI 2014C, 2009C)
Alcohols, Phenols and Ethers 5

84. Illustrate the following name reaction : 92. The boiling points of ethers are much lower
Williamson Synthesis than those of the alcohols of comparable molar
(1/3, Delhi 2012C, 1/2 Delhi 2010) masses. (1/3, Delhi 2007)
85. Write IUPAC name of the following : SA I (2 marks)
93. Write the mechanism of the following reaction :
(1/3, AI 2012C)
2CH3CH2OH

86. Explain the following giving one example : CH3CH2 O CH2 CH3
Friedel Craft’s acetylation of anisole. (Delhi 2016, 2015, 2013)
(1/3, Delhi 2011) 94. Give reasons for the following :
87. Account for the following : (i) Boiling point of ethanol is higher in
Preparation of ethers by acid dehydration of comparison to methoxymethane.
secondary or tertiary alcohols is not a suitable (ii) (CH3)3C—O—CH3 on reaction with HI
method. (1/3, Delhi 2011C, 1/2, Delhi 2008) gives CH3OH and (CH3)3C—I as the
88. Account for the following : main products and not (CH3)3C—OH and
The boiling points of ethers are lower than CH3I. (2/3, AI 2015)
isomeric alcohols. (1/3, AI 2011C) 95. Give mechanism of preparation of ethoxy
89. Phenylmethyl ether reacts with HI to give ethane from ethanol. (Delhi 2013C)
phenol and methyl iodide and not iodobenzene 96. How is 1-propoxypropane synthesised from
and methyl alcohol. Why? (Delhi 2010C) propan-1-ol? (Delhi 2010)
90. Describe the following : 97. Name the reagents and write the chemical
Unsymmetrical ether (1/2, AI 2009C) equations for the preparation of the following
91. Why is the preparation of ether by acid compounds by Williamson’s synthesis :
dehydration of secondary alcohol not a suitable (i) Ethoxybenzene
method? (AI 2008C) (ii) 2-Methyl-2-methoxypropane (AI 2008)