CHEMISTRY

CHAPTER-7 ALCOHOLS,PHENOLS & ETHERS

NCERT BOARD MCQ’S YEAR WISE:

March-2024

1. Williamson’s synthes is of preparing dimethyl ether isa/an ____________.

a) electrophilic substitution b) SN1 reaction
c) electrophilic addition d) SN2 reaction
2. The reaction of an alkyl halide with sodium alkoxide forming ether is known as
_________.
a) Wurtz reaction b) Reimer- Tiemann reaction
c) Williamson synthesis d) Kobe reaction
3. The correct order of the ease of dehydration of the following alcohols by the
action of conc H2SO4 is _________.
a) (CH3)3 C – OH > (CH3)2 CH – OH > CH3 CH2 – OH
b) (CH3)2 CH – OH > CH3 CH2 – OH > (CH3)3 C – OH
c) CH3 CH2 – OH > (CH3)2 CH – OH > (CH3)3 C – OH
d) (CH3)2 CH – OH > (CH3)3 C – OH > CH3 CH2 – OH
4. Dehydration of tertiary alcohols with Cu at 573 K gives _________.
a) Alkyne b) Alkene
c) Aldehyde d) Ketone
5. Phenol on reaction with aqueous bromine at room temperature gives _______.
a) 2-bromophenol b) 3-bromophenol
c) 4-bromophenol d) 2,4,6 tribromophenol
6. Phenol does not undergo nucleophilic substitution reaction easily due to _____.
a) Partial double bond character of C – OH bond.
b) Partial double bond character of C – C bond.
c) Acidic nature of phenol.
d) Instability of phenoxide ion.
7. The suitable Grignard reagent used for the synthesis of CH3 – CH – CH2 – OH
with methanal is _________.
CH3
a) (CH3)2 CH – CH2 MgBr / H2O
b) CH3 MgBr / H2O
c) (CH3)2 CH – MgBr / H2O
d) CH3CH2CH2 MgBr / H2O
8. Which of the following is most acidic?
a) b)

c) d)
9. Ethanol on heating with conc H2SO4 at 413 K gives _________.
a) C2H5OSO3H b) C2H5 – O –CH3
c) C2H5 – O – C2H5 d) CH2 = CH2
10. Anisole reacts with HI to give _________.
a) b)

c) d)

11. Phenol is less acidic than _________.

a) ethanol b) o-nitrophenol
c) o-methoxyphenol d) o-methylphenol
12. (CH3)3 C – O – CH3 reacts with HI to give _________.
a) (CH3)3 C – I + CH3OH b) (CH3)3 C – I + CH3 I
c) (CH3)3 C – OH + CH3 I d) (CH3)3 C – OH + CH3 OH
13. Which of the following is most acidic?
a) b)

c) d)
14. (CH3)2 CH – O – CH3 reacts with HI to give _________.
a) (CH3)2 CH – OH + CH3 – OH b) (CH3)2 CH – OH + CH3 – I
c) (CH3)2 CH – I + CH3 – OH d) (CH3)2 CH – I + CH3 – I
15. Which one of the following compounds has the lowest pKa value?
a) p-cresol b) p-nitrophenol
c) m-nitrophenol d) 2,4,6 trinitrophenol
16. Which one of the following compounds has the lowest pKa value?
a) p-nitrophenol b) m-nitrophenol
c) p-cresol d) 2,4,6 trinitrophenol
17. C6H5 – O – CH3 reacts with HI to give _________.
a) C6H5 – I + CH3 OH b) C6H5 OH + CH3 I
c) C6H5 OH + CH3 OH d) C6H5 – I + CH3 I
18. Consider the following reaction:

a) b)

c) d)

19. Which of the following Grignard reagent will be used with methanal to prepare

a) b)

c) d)

20. CH3 – O – CH3 reacts with HI to give _________.

a) CH3 – OH + CH3 – I b) 2 CH3 – OH
c) 2 CH3 – I d) CH3 – I
21. Nucleophilic addition of Grignard reagent to ketones followed by hydrolysis
with dilute acids forms_________.
a) Alkene b) Primary alcohol
c) Tertiary alcohol d) Secondary alcohol
22. Match the reagents required for the given reactions:
a) Oxidation of primary alcohols (p) NaBH4
to alcohols.
b) Butan -2-one to Butan-2-ol (q) 85% phosphoric acid
c) Bromination of phenol to 2,4,6 tribromophenol (r) PCC
d) Dehydration of propan-2-ol to propene (s) Bromine water
a) I – (r), II – (p), III – (s), IV – (q) a) I – (q), II – (r), III – (p), IV – (s)
c) I – (s), II – (q), III – (p), IV – (r) d) I – (p), II – (s), III – (r), IV – (q)
23. Out of the following alkenes, the one which will produce tertiary butyl alcohol
on acid catalyzed hydration is _________.
a) CH3 CH2 CH = CH2 b) CH3 CH = CH2
c) CH3 – CH = CH – CH3 d) ( CH3 )2 C = CH2
24. Which of the following species can act as the strongest base?
a) OH- b) C6H5O-
c) RO- d)

25. Visha took 4 test-tubes namely A,B,C & D containing CH3 CH = CH2 ,
CH3CH2CH =CH2 , CH3 CH = CH − CH3 and (CH3)2C = CH2 respectively and tried to
convert them into tertbutyl alcohol. She carried out acid catalysed hydration
reaction on every alkene. Out of the four test-tubes, the one which will give
desired result is _________.
a) A b) B c) C d) D
 March-2023

1. In the reaction what is the correct

order of reactivity of alcohols?
a) 1o < 2o < 3o b) 1o > 3o > 2o
c) 1o > 2o > 3o d) 3o > 1o > 2o
2. When benzene diazonium chloride reacts with phenol, it forms a dye. This
reaction is called __________.
a) Diazotisation reaction. b) Condensation reaction.
c) Coupling reaction d) Acetylation reaction
3. When benzene diazonium chloride on hydrolysis gives _________.
a) Phenol b) Chlorobenzene
c) Benzene d) Aniline
4. For the conversion of propene into 1-propanol, which of the following reagents
and conditions should be used?
a) Conc H2SO4 ; H2O and heat b) B2H6 ; H2O2 / OH –
c) Dilute H2SO4 d) H2O / H +
5. When diethyl ether is heated with excess of HI, it produces _________.
a) ethanol b) iodoform
c) methyl iodide d) ethyl iodide
6. The product formed in the reaction is _________.
7. Which of the following alkenes on acid catalyzed hydration gives a tertiary
alcohol?
a) 2-butene b) 2-methyl propene
c) Propene d) 1-butene
8. 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

NCERT BOARD ASSERTION/REASON YEAR WISE:

Option A : Both Assertion and Reason are true and Reason is the
correct explanation of the assertion.

Option B : Both Assertion and Reason are true but Reason is not the
correct explanation of the assertion.

Option C : Assertion is true but Reason is false.

Option D : Assertion is false, but Reason is true.

March-2024

1. Assertion : p- nitrophenol is less acidic than phenol.

Reason : Nitro group is electron withdrawing and helps in the
stabilization of p-nitrophenoxide ion.

Option A : Both Assertion and Reason are true and Reason is the
correct explanation of the assertion.
2. Assertion : Bromination of phenol can be carried out even in the absence
of Lewis acid.
Reason : – OH group of alcohol has the high activation effect.

Option A : Both Assertion and Reason are true and Reason is the
correct explanation of the assertion.

3. Assertion : Phenols are stronger acids than alcohols.

Reason : Alkoxide ion is more stable than phenoxide ion.

Option C : Assertion is true but Reason is false.

4. Assertion : p-methoxy phenol is a stronger acid than p-nitrophenol.

Reason : Methoxy group shows +I effect whereas nitro group shows –I
effect.

Option D : Assertion is false, but Reason is true.

5. Assertion : p-methoxy phenol is a stronger acid than p-nitrophenol.

Reason : Methoxy group exerts +R effect at both ortho and para
position.

Option D : Assertion is false, but Reason is true.

NCERT BOARD 1/2/3 MARKS YEAR WISE:

March-2024
1. Write the reaction involved in the following : 1+1=2
(a) Reimer-Tiemann reaction (b) Kolbe’s reaction
2. What happens when: (Any three) 3 x 1=3

(a) is treated with CH3CHO followed by hydrolysis.

 (b) Phenol is treated with conc. (HNO3 + H2SO4).
(c) Anisole is treated with CH3COCl in the presence of anhydrous AlCl3.
(d) Propan-2-ol is heated with Cu at 573 K.

3. What happens when : (any three) 3

(a) CH3MgBr is treated with cyclohexanone followed by hydrolysis
(b) Phenol is treated with Br2 in the presence of CS2
(c) Benzene diazonium chloride is treated with H2O
(d) Anisole is treated with HI.

4. (a) Write the mechanism of the following reaction.

(b) Write the main product in each of the following reaction.

5. Give the equations or reactions for the preparation of: { Any 3 } 3

(a) Phenol from chlorobenzene
(b) Salicylaldehyde from phenol
(c) 2-methoxyacetophenone from anisole
(d) Picric acid from phenol

6. Name the reagent used in the bromination of phenol to form 2,4,6-

tribromophenol. 1

7. Write chemical equations for the following reactions: 3

 (a) Hydroboration – Oxidation reaction.
(b) Williamson synthesis
(c) Friedel – Crafts alkylation of anisole.

8. Give the structure of the major product expected from the following reactions:
3
(a) Reaction of ethanal with methyl magnesium bromide followed by
hydrolysis.
(b) Hydration of But-1-ene in the presence of dilute sulphuric acid.
(c) Reaction of phenol with bromine water.

March-2023
1. Account for the following: 2
i) Phenol is a stronger acid than alcohol.
ii) The boiling point of alcohols decreases with increase in branching of
alkyl chain.

2. How do you convert the following: { Any 3 } 3

(a) Phenol to picric acid
(b) Propanone to 2-methylpropan-2-ol
(c) Phenol to anisole
(d) Propene to propan-1-ol

3. Predict the products of the following reactions: 2

4. Give reasons for the following: 1

i) p-nitrophenol is more acidic than p-methylphenol.

5. How do you convert the following: { Any 3 } 3

(a) Phenol to 2-hydroxybenzaldehyde
(b) Anisole to 2-methoxyacetophenone.
 (c) Ethanol to ethanal
(d) Propene to propan-2-ol

6. Write chemical equation for the following reaction: 1

Acetylation of salicylic acid.

7. Why ortho nitrophenol is steam volatile while para nitrophenol is not? 1

8. What happens when: 3

i) Anisole is treated with CH3Cl/anhydrous AlCl3?
ii) Phenol is oxidized with Na2Cr2O7 / H+ ?
iii) (CH3)3 C – OH is heated with Cu/573 K?
Write chemical equation in support of your answer.

9. Write chemical equation for the following reaction: 2

(a) Kolbe’s reaction.
(b) Williamson synthesis

10. Write the structures and IUPAC name of the products expected from the
following reactions:
(a) Reaction of methanal with (CH3)2 CH MgBr followed by hydrolysis.
(b) Reaction of phenol with Conc.HNO3 .

11. Write the equation of the reaction for the preparation of phenol from cumene. 1

12. Show how you will synthesise: 2

13. (a) Write the mechanism of the following reaction: 3

(b) Write the structures of the products obtained by heating:

14. Write the structures and IUPAC name of the products expected from the 2
following reactions:
(a) Reaction of methanal with followed by hydrolysis.

(b) Reaction of phenol with Br2(aq) .

15. Write the products of the following reaction: 2

i)

ii) Why is p-nitrophenol more acidic than phenol?

16. What happens when phenol reacts with 2

i) Conc. HNO3 and
ii) CHCl3 in presence of aqueous NaOH followed by acidification.

17. For the pair, phenol and cyclohexanol, answer the following: 2
(a) Why is phenol more acidic than cyclohexanol?
(b) Give one chemical test to distinguish between the two.

18. i) Why is the C – O bond length in phenols less than that in methanol? 3
ii) Arrange the following in order of increasing boiling point:
Ethoxyethane, Butanal, Butanol, n-butane.
iii) How can phenol be prepared from anisole? Give reaction.
 March-2022
1. Write a chemical test to distinguish phenol and benzoic acid. 1

2. Convert Propan-1-ol to 2-Bromopropanoic acid. 1

March-2021
3. Write the structures of the products formed when: 2
i) Propan-2-ol is heated with Cu at 573 K.
ii) Salicylic acid is treated with (CH3 CO)2O / H+

4. Carry out the following conversions: 2

i) Phenol to Anisole
ii) Aniline to phenol

5. Write equations of the following reactions: 2

i) Friedel Crafts reaction – Alkylation of anisole
ii) Nitration of phenol with concentrated nitric acid

6. Write the structures of the products when 2

i) Phenol is treated with bromine water and
ii) Propanol is heated with Cu at 573 K.

7. Carry out the following conversions. 2

i) Ethanol to ethyl cyanide
ii) Phenol to acetophenone

8. Write the name of reagents used in the following reactions: 2

i) CH3CHO ? CH3CH2OH

ii) ?
 March-2020
1. Out of t-butyl alcohol and n-butanol, which one will undergo acid catalyzed
dehydration faster and why? 2

2. Write the structures of the products formed when anisole is treated with HI ? 1

3. Carry out the following conversions. 3

i) Phenol to Salicylaldehyde
ii) t-butyl chloride to t-butyl ether
iii) Propene to propanol

4. Give the mechanism for the formation of ethanol to ethene. 2

5. Predict the reagent for carrying out the following conversions: 3

i) Phenol to benzoquinone
ii) Anisole to p-bromoanisole
iii) Phenol to 2,4,6, tribromophenol

6. Write the structures of the products formed when ethoxybenzene is treated

with HI ? 1

7. Bond angle in alcohol is slightly less than the tetrahedral angle. 1

8. C – OH bond length in CH3OH is slightly more than the C – OH bond length in

phenol. 1

9. The IUPAC name for . 1

10. Write the mechanism of the following reaction. 2

11. Write the preparation of phenol from cumene. 1

12. Give the structures of final products expected from the following reactions: 3

a) Hydroboration of propene followed by oxidation with H 2O2 in alkaline

medium.

b) Dehydration of (CH3)3 C – OH by heating it with 20% H3PO4 at 358 K.

c) Heating of with HI.

13. How can you convert the following? 3

i) Phenol to o – hydroxybenzaldehyde
ii) Methanal to methanol
iii) Phenol to phenyl ethanoate

14. How will you convert: 2

a) Phenol to Picric acid
b) Ethanal to Propan-2-ol

March-2019

1. How do you convert the following: 2

i) Phenol to Anisole
ii) Ethanol to Propan-2-ol

2. Write the mechanism of the following reaction: 2

3. Why phenol undergoes electrophilic substitution more easily than benzene? 1

4. Account for the following: 2

i) o- nitrophenol is more steam volatile than p-nitrophenol.
 ii) t-butyl chloride on heating with sodium methoxide gives
2-methylpropene instead of t-butylmethyl ether.

5. Write the reaction involved in the following: 2

i) Reimer – Tiemann reaction.
ii) Friedel- Crafts Alkylation of phenol.

6. Give chemical test to distinguish between ethanol and phenol. 1

7. Give reactions of the following reactions: 3

i) Phenol is treated with conc.HNO3
ii) Propene is treated with B2H6 followed by H2O2 / OH –
iii) Sodium t-butoxide is treated with CH3Cl

8. How will you distinguish between butan-1-ol and butan-2-ol? 2

9. Arrange the following in increasing order of acidity: 1

Phenol, ethanol, water

10. How can you obtain phenol from 3

i) Cumene
ii) Benzene sulphonic acid
iii) Benzene diazonium chloride

11. Write the structure of the major product obtained from dinitration of 3-methyl
phenol. 1

12. Write the Kolbe’s reaction. 2

13. Arrange the following in increasing order of their acidic character: 1

Benzoic acid, Phenol, Cresol

14. Out of , Which one is optically active and why? 1

15. What happens when
a) Phenol is oxidized with Na2Cr2O7 / H+ ?
b) Anisole is treated with CH3Cl/ anhydrous AlCl3

16. Arrange the following in increasing order of their acidic character: 1

Ethanol, Phenol, Water

17. Write: 2
a) Reimer Tiemann reaction.
b) Williamson’s synthesis

18. How will you synthesize the following alcohol from appropriate alkene: 2

19. Write the mechanism of the following reaction: 2

20. Give reactions of the following reactions: 2

a) Kolbe’s reaction
b) Friedel Crafts alkylation of anisole

21. Show how will you synthesize the following alcohol prepared by the reaction of
a suitable Grignard reagent on methanal? 2

22. Write the mechanism of the following reaction: 2

23. Butan-1-ol has a higher boiling point than diethyl ether. Why? 1

24. Write the mechanism of the following reaction: 2

25. Convert: 2
a) Phenol to toluene
b) Ethanol to ethanal

26. Give one chemical test to distinguish between the following: 3

a) Phenol and 1-propanol
b) Ethanol and dimethyl ether
c) 1-propanol and 2-methyl-2-propanol

27. Write the products of the following reactions: 3

March-2018
1. Write the IUPAC name of the following: 1
 March-2017
1. Write the IUPAC name of the following: 1

2. Arrange the following in increasing order of their acidic character: 1

p-cresol, Phenol, p-nitrophenol

3. Write the mechanism (using curved arrow notation) of the following reaction: 2

4. Write the structures of the products when butan-2-ol reacts with the following:
2
a) CrO3

b) SOCl2

5. Write the IUPAC name of the following: 1

6. Write the IUPAC name of the following: 1

7. Write the products in the following reaction: 3

8. Give simple tests to distinguish between the following pairs of compounds: 2

i) Ethanol and Phenol
ii) Propanol and 2-methyl-2-propanol

9. Write the formula of reagents used in the following reactions: 2

i) Bromination of phenol to 2,4,6 trinitrophenol
ii) Hydroboration of propene and then oxidation to phenol

10. Arrange the following compound groups in the increasing order of their 2
property indicated:
a) p-nitrophenol , ethanol, phenol ( Acidic character )
b) Propanol, Propane , Propanal ( Boiling point )

11. Write the mechanism (using curved arrow notation) of the following reaction: 2

12. Write the IUPAC name of the following: 1

13. What happens when 3
a) (CH3)3 C – OH is treated with Cu at 573 K.
b) Anisole is treated with CH3Cl/Anhydrous AlCl3
c) Phenol is treated with zinc dust.

March-2016

1. Write the IUPAC name of the given compound: 1

2. Write the final product in each of the following reaction: 3

3. Write the products of the following reactions: 3

4. Write the equation for: 2

a) Reimer-Tiemann reaction
b) Friedel Crafts alkylation of anisole

5. What happens when Phenol reacts with Conc. HNO 3 1

6. Distinguish between
a) Ethanol and Phenol
b) Propan-2-ol and 2-methyl-2-propanol

March-2015

1. Write the IUPAC name of the given compound: 1

2. Give reasons for the following: 3

i) Phenol is more acidic than ethanol.
ii) Boiling point of ethanol is higher in comparison to methoxymethane.
iii) (CH3)3C – O – CH3 on reaction with HI gives CH3OH and (CH3)3 – I as the
main products and not (CH3)3C – OH and CH3I.
3. How will you convert the following? 1
Aniline to phenol

March-2014

1. Write the equations involved in the following reactions: 2

i) Reimer-Tiemann reaction
ii) Williamson’s synthesis

March-2013
1. How will you convert ethanol to ethane? 1
2. How would you obtain the following: 3
(i) Benzoquinone from phenol
(ii) 2-Methylpropan-2-ol from methylmagnesium bromide
(iii) Propan-2-ol from propene

March-2012

1. Explain the mechanism of acid catalyzed hydration of an alkene to form

corresponding alcohol. 2

2. Explain the following behaviours:

i) Alcohols are more soluble in water than the hydrocarbons of comparable
molecular mass.
ii) Ortho-nitrophenol is more acidic than ortho-methoxyphenol.