Sure Shot Questions

Chapter – 07
Alcohols, Phenols and Ethers
MCQ (1 mark)

1. Monochlorination of toluene in sunlight followed

by hydrolysis with aq. NaOH yields
(a) I, II, III, IV (b) I, IV
(a) o-cresol
(c) II, III (d) I
(b) m-cresol
(c) 2, 4-dihydroxytoluene
(d) Benzyl alcohol.
7. Give IUPAC name of the compound given below:

2. How many alcohols with molecular formula C4H10O

(a) 2-Chloro-5-hydroxyhexane
are chiral in nature?
(b) 2-Hydroxy-5-chlorohexane
(a) 1 (b) 2
(c) 5-Chlorohexan-2-ol
(c) 3 (d) 4
(d) 2-Chlorohexan-5-ol

3. What is the correct order of reactivity of alcohols

8. IUPAC name of m-cresol is
in the following reaction?
(a) 3-methylphenol
R  OH  HCl 
ZnCl2
 R  Cl  H 2O (b) 3-chlorophenol
(a) 10 > 20 > 30 (b) 10 < 20 > 30 (c) 3-methoxyphenol
(c) 30 > 20 > 10 (d) 30 > 10 > 20 (d) Benzene-1, 3-diol.
4. CH3CH2OH can be converted into CH3CHO by
(a) Catalytic hydrogenation
(b) Treatment with LiAlH4 9. IUPAC name of the compound
(c) Treatment with pyridinium chlorochromate
(d) Treatment with KMnO4.
5. The process of converting alkyl halides into
alcohols involves is
(a) Addition reaction (a) 1-methoxy-1-methylethane
(b) Substitution reaction (b) 2-methoxy-2-methylethane
(c) Dehydrohalogenation reaction (c) 2-methoxypropane
(d) Rearrangement reaction. (d) isopropylmethyl ether.
6. Which of the following compounds is aromatic
alcohol?
10. Which of the following species can act as the
strongest base?
 
(a) OH (b) OR

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 16. Arrange the following compounds in increasing
order of boiling point.
(c)  OC6 H 5 (d)
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
11. Which of the following compounds will react with (b) Propan-l-ol,butan-l-ol,butan-2-ol,pentan-l-ol
sodium hydroxide solution in water? (c) Pentan-l-ol,butan-2-ol,butan-l-ol,propan-l-ol
(a) C6 H 5OH (b) C6 H5CH 2OH (d) Pentan-1 -ol, butan-l-ol, butan-2-ol, propan-l-ol
(c) (CH3 )3 COH (d) C2 H 5OH

17. The correct IUPAC name of

12. Phenol is less acidic than

(a) Ethanol
(b) o-nitrophenol
(c) o-methylphenol [2020]
(d) o-methoxyphenol. (a) Tert-butyl alcohol
(b) 2,2-Dimethylpropanol
(c) 2 – Methylbutan – 2 – ol
13. Which of the following is most acidic?
(a) Benzyl alcohol (d) 3 – Methylbutan – 3 – ol
(b) Cyclohexanol 18. The C – O – H bond angle in alcohol is
(c) Phenol [Term I, 2021 – 22]
(d) m-Chlorophenol
(a) Slightly greater than 109028’
(b) Slightly less than 109028’

14. Mark the correct order of decreasing acid strength (c) Slightly greater than 1200
of the following compounds. (d) Slightly less than 1200
19. Which of the following alcohols will not undergo
oxidation?
(a) Butanol (b) Butan-2-ol
(c) 2-Methylbutan-2-ol (d) 3-Methylbutan-2-ol
(a) (v) > (iv) > (ii) > (i) > (iii)
(b) (ii) > (iv) > (i) > (iii) > (v) 20. In the reaction R – OH + HCl 
ZnCL2

(c) (iv) > (v) > (iii) > (ii) > (i) RCl + H2O, what is the correct order of reactivity of
(d) (v) > (iv) > (iii) > (ii) > (i)
alcohol? [2023]
(a) 10 < 20 < 30 (b) 10 > 30 > 20
15. Mark the correct increasing order of reactivity of (c) 10 > 20 > 30 (d) 30 > 10 > 20
the following compounds with HBr/HCl. 21. In the following reaction,
CH3  CH  CH  CH 2  OH 
PCC

The product formed is
[Term I, 2021 – 22]
(a) CH3  CHO and CH3CH 2OH
(a) (i) < (ii) < (iii) (b) (ii) < (i) < (iii)
(c) (ii) < (iii) < (i) (d) (iii) < (ii) < (i) (b) CH3  CJ  CH  COOH

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 (c) CH3  CH  CH  CHO (b) Both Assertion (A) and Reason (R) are correct

(d) CH3  CH 2  CH 2  CHO statements, but Reason (R) is not the correct
explanation of the Assertion (A).
22. Which of the following acids reacts with acetic
(c) Assertion (A) is correct, but Reason (R) is
anhydride to form aspirin?
incorrect statement.
(a) Benzoic acid (b) Salicylic acid
(d) Assertion (A) is incorrect, but Reason (R) is
(c) Phthalic acid (d) Acetic acid
correct statement. [2020]

23. The conversion of an alkyl halide into an alcohol by 26. Assertion (A) : o-nitrophenol is a weaker acid than

aqueous NaOH is classified as p-nitrophenol.

(a) a dehydrohalogenation reaction Reason (R) : Intramolecular hydrogen bonding

(b) a substitution reaction makes ortho isomer weaker than para isomer.

(c) an addition reaction (a) Both assertion (A) and reason (R) are correct

(d) a dehydration reaction [2020] statements, and reason (R) is the correct
explanation of the assertion (A).
(b) Both assertion (A) and reason (R) are correct
24. Identify the secondary alcohols from the following
statements, but reason (R) is not the correct
set:
explanation of the assertion (A).
(i) CH3CH 2CH (OH) CH3
(c) Assertion (A) is correct, but reason (R) is
(ii) (C2 H5 )3 COH
incorrect statement.
(d) Assertion (A) is incorrect, but reason (R) is
correct statement. [2020]

27. Assertion (A) : Alcohols have higher boiling point

than alkanes of comparable molecular mass.
(a) (i) and (iv) (b) (i) and (iii)
Reason (R) : Alcohols have intramolecular
(c) (i) and (ii) (d) (i), (iii) and (iv)
hydrogen bond.
[Term I, 2021 – 22]
(a) Both Assertion (A) and Reason (R) are correct
statements, and Reason (R) is the correct
Assertion-Reasoning (1 mark)
explanation of Assertion (A).
(b) Both Assertion (A) and Reason (R) are correct
25. Assertion (A): The C—O—H bond angle in statements, but Reason (R) is not the correct
alcohols is slightly less than the tetrahedral angle. explanation of Assertion (A).
Reason (R): This is due to the repulsive interaction (c) Assertion (A) is correct, but Reason (R) is
between the two lone electron pairs on oxygen. incorrect statement.
(a) Both Assertion (A) and Reason (R) are correct (d) Assertion (A) is incorrect, but Reason (R) is
statements, and Reason (R) is the correct correct statement. [2020C]
explanation of the Assertion (A).

28. Assertion (A): (CH3 )3 C  O  CH3 gives

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 (CH3 )3 C  I and CH3OH on treatment with HI.
(a) Both Assertion (A) and Reason (R) are correct
statements, and Reason (R) Is the correct
explanation of the Assertion (A).
(b) Both Assertion (A) and Reason (R) are correct
statements, but Reason (R) Is not the correct
explanation of the Assertion (A).
(c) Assertion (A) is correct, but Reason (R) is
incorrect statement.
(d) Assertion (A) is incorrect, but Reason (R) is
correct statement. [2020]
29. Assertion (A) : The C-O-C bond angle in ethers is
slightly less than tetrahedral angle.
Reason (R): Due to the repulsive interaction
between the two alkyi groups in ethers.
(a) Both Assertion (A) and Reason (R) are correct
statements, and Reason (R) Is the correct
explanation of the Assertion (A).
(b) Both Assertion (A) and Reason (R) are correct
statements, but Reason (R) Is not the correct
explanation of the Assertion (A).
(c) Assertion (A) is correct, but Reason (R) Is
wrong statement.
(d) Assertion (A) Is wrong, but Reason (R) Is
correct statement. [2020]
30. Given below are two statements labelled as
Assertion (A) and Reason (R).
Assertion (A) : An ether is more volatile than an
alcohol of comparable molecular mass. Reason
(R): Ethers are polar in nature.
Select the most appropriate answer from the
options given below:
(a) Both A and R are true and R is the correct
explanation of A.
(b) Both A and R are true but R is not the correct
explanation of A.
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(c) A is true but R is false.
(d) A is false but R is true. [2022 – 23]
31. Assertion : Methoxyethane reacts with HI to give
ethanol and iodomethane.
Reason : Reaction of ether with HI follows SN2
mechanism.
(a) Assertion and reason both are correct
statements and reason is correct explanation
for assertion.
(b) Assertion and reason both are correct
statements but reason is not correct
explanation for assertion.
(c) Assertion is correct statement but reason is
wrong statement.
(d) Assertion is wrong statement but reason is
correct statement. [2020 – 21]
Case Study
Read the passage given below and answer the
following questions (Q. No. 1 to 3):
32. Alcohols and phenols are acidic in nature. Electron
withdrawing groups in phenol increase its acidic
strength and electron donating groups decrease it.
Alcohols undergo nucleophilic substitution with
hydrogen halides to give alky! halides. On oxidation
primary alcohols yield aldehydes with mild oxidising
agents and carboxylic acids with strong oxidising
agents while secondary alcohols yield ketones.
The presence of — OH groups in phenols activates the
ring towards electrophilic substitution. Various
important products are obtained from phenol like
salicylaldehyde, salicylic acid, picric acid etc.
1. Which of the following alcohols is resistant to
oxidation?
(a) CH 3O  (b) CH 3 
(c) NO2  (d) All of these
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2. Which of the following groups increases the acidic (b)The compound that does not liberate CO2, on
character of phenol? treatment with aqueous sodium bicarbonate solution
is
(a) CH 3O  (b) CH 3  a) Benzoic acid
b) Benzenesulphonic acid
(c) NO2  (d) All of these
c) Carbolic acid
3. Consider the following reaction: d) Salicylic acid

(c) The correct order of acidic strength among the

following Is

The products X and Y are

[Term I, 2021 – 22]

33. Read the text carefully and answer the questions:

Both alcohols and phenols are acidic in nature, but
phenols are more acidic than alcohols. Acidic
strength of alcohols mainly depends upon the
inductive effect. Acidic strength of phenols
depends upon a combination of both inductive
effect and resonance effects of the substituent and
its position on the benzene ring. Electron
withdrawing groups increases the acidic strength
of phenols whereas electron - donating groups
decreases the acidic strength of phenols. Phenol is
a weaker acid than carboxylic acid.

(a) Phenols are highly acidic as compare to alcohols

due to
a) Phenoxide ion is resonance stabilised
b) The stronger hydrogen bonds in phenols
c) Alkoxide ion is a strong conjugate base
d) The higher molecular mass of phenols

Questions

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34. Write the IUPAC name of the given compound:
[Foreign 2015]

35. Write the preparation of phenol from cumene.

36. Write the structures of the main products in the following reactions:

37. Write the product(s) in the following reactions:

38. Give one chemical test to distinguish between the following:

(a) Phenol and 1-propanol
(b) Ethanol and dimethyl ether
(c) 1-propanol and 2-methyl-2-propanol
39. Write the equations for the following reactions:
(a) Salicylic acid is treated with acetic anhydride in the presence of conc. H2SO4.
(b) tert-Butyl chloride is treated with sodium ethoxide.
(c) Phenol is treated with chloroform in the presence of NaOH.
40. Write the IUPAC name of the given compound:

41. Give the strcture and IUPAC name of the product formed when propanone is reacted with methylmagnesium
bromide followed by hydrolysis.

42. Write the structures of the main products in the following reactions:

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43. Give simple chemical tests to distinguish between the following pairs of compounds:
(i) Ethanol and phenol
(ii) Propanol and 2-methylpropan – 2 –ol.

44. How do you convert

(i) phenol to toluene?
(ii) formaldehyde to ethanol?

45. Explain why p-nitrophenol is more acidic than phenol.

46. Ortho and para - nitrophenols are more acidic than phenol. Draw the resonance sstructures of the corresponding
phenoxide ions.

47. Write the main product (s) in each of the following reactions:

48. (a) Arrange the following compounds in the increasing order of their acid strength:
𝑝 − 𝑐𝑟𝑒𝑠𝑜𝑙, 𝑝 − 𝑛𝑖𝑡𝑟𝑜𝑝ℎ𝑒𝑛𝑜𝑙, 𝑝ℎ𝑒𝑛𝑜𝑙
(b) Write the mechanism (using curved arrow notation) of the following reaction:
𝐻3 𝑂 +
𝐶𝐻2 = 𝐶𝐻2 → 𝐶𝐻3 − 𝐶𝐻2+ + 𝐻2 𝑂

49. Answer the following question:

(i) Dipole moment of phenol is smaller that the of methanol. Why?
(ii) In Kolbe’s reaction, instead of phenol, phenoxide ion is treated with carbon dioxide. Why?

50. Explain the following behaviours:

(i) Alcohols are more soluble in water than the hydrocarbons of comparable molecular masses.
(ii) Ortho-nitrophenol is more acidic than ortho-methoxyphenol.
(iii) Cumene is a better starting material for the preparation of phenol.

51. Write the main products (s) in each of the following reactions:

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52. How do you convert the following?
(i) Phenol to anisole
(ii) Propan – 2- oI to 2- Methyl propan – 2- oI
(iii) Aniline to phenol.

53. A compound ‘A’ having molecular formula 𝐶4 𝐻10 𝑂 is found to be soluble in concentrated sulphuric acid. It does
not react with sodium metal or potassium permanganate. On heating with excess of HI, it gives a single alkyl
halide. Deduce the structure of compound A and explain all the reactions.

54. Give reasons for the following:

(a) Protonation of phenols is difficult whereas ethanol easily undergoes protonation.
(b) Boiling point of ethanol is ethanol is higher than that of dimethyl ether.

55. How do you convert the following:

(i) Phenol to anisole
(ii) Propan-2-ol to 2-methylpropan-2-ol
(iii) Aniline to phenol

56. Explain why is orthonitrophenol more acidic than orthomethosyphenol?

57. Give Reasons:

(i) Relative ease of dehydration of alcohols is 30 > 20 > 10 .
(ii) 𝑜 − 𝑛𝑖𝑡𝑟𝑜𝑝ℎ𝑒𝑛𝑜𝑙 is more acidic than 𝑜 − 𝑚𝑒𝑡ℎ𝑜𝑥𝑦𝑝ℎ𝑒𝑛𝑜𝑙.

58. (a) Answer the following questions.

(i) Among HI, HBr, HCI, HI is most reactive towards alcohols. Why?
(ii) Of the two alcohols: (a) 𝐶𝐻2 = 𝐶𝐻 − 𝐶𝐻2 𝑂𝐻 𝑎𝑛𝑑 (𝑏)𝐶𝐻2 = 𝐶𝐻 − 𝐶𝐻2 − 𝐶𝐻2 𝑂𝐻, which one will react
more easily with conc. HCI in the presence of 𝑍𝑛𝐶𝐼2 ?
(b) Arrange the following compounds in the increasing order of their acid strengths: 4-nitrophenil, phenol,
2,4,6-trinitrophenol

59. How are the following conversions carried out?

(i) Propene → Propan – 2 - oI
(ii) Benzyl chloride → Benzyl alcohol
(iii) Ethyl magnesium chloride → Propan – 1- oI
(iv) Methyl magnesium bromide bromide → 2-Methyl-propan -2-oI

60. Arrange the following sets of compounds in order of their increasing boiling points:
(a) Pentan-1-oI, butan-1-oI, butan-2-oI, ethanol, propan -1-oI, methanol
(b) Pentan -1-oI, n-butane, pentanal, cthoxyethane.

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