Worksheet On Alcoholss, Phenols and Ethers

WORKSHEET ON ALCOHOLS, PHENOLS AND ETHERS
1. (a) Out of t-butyl alcohol and n-butanol, which one will undergo acid catalysed dehydration faster
and why?
(b) Carry out the following conversions :
(i) Phenol to Salicylaldehyde
(ii) t-butylchloride to t-butyl ethyl ether
(iii) Propene to Propanol
2 (a) Give the mechanism for the formation of ethanol from ethene.
(b) Predict the reagent for carrying out the following conversions :
(i) Phenol to benzoquinone
(ii) Anisole to p-bromoanisole
(iii) Phenol to 2,4,6-tribromophenol
3. Give reasons for the following :
(a) Bond angle in alcohol is slightly less than the tetrahedral angle.
(b) C – OH bond length in CH3OH is slightly more than the C – OH bond length in phenol.
4. (a) How can you convert the following :
(i) Sodium phenoxide to o-hydroxybenzoic acid
(ii) Acetone to propene
(iii) Phenol to chlorobenzene
(b) Write the preparation of phenol from cumene.
5. Write the equation for the preparation of 2-methyl-2-methoxypropane by Williamson synthesis.
6. Give the structures of final products expected from the following reactions :
(i) Hydroboration of propene followed by oxidation with H2O2 in alkaline medium.
(ii) Dehydration of (CH3)3C–OH by heating it with 20% H3PO4 at 358 K.
7. How can you convert the following?
(i) Phenol to o-hydroxybenzaldehyde.
(ii) Methanal to ethanol

(iii) Phenol to phenyl ethanoate.
8. (a) How do you convert the following :
(i) Phenol to Anisole
(ii) Ethanol to Propan-2-ol
(b) Why phenol undergoes electrophilic substitution more easily than benzene?
9. (a) Account for the following :
(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-butylmethylether.
(b) Write the reaction involved in the following :
(i) Reimer-Tiemann reaction
(ii) Friedal-Crafts Alkylation of Phenol
(c) Give simple chemical test to distinguish between Ethanol and Phenol.
10. (a) Give equations of the following reactions :
(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.
(b) How will you distinguish between butan-1-ol and butan-2-ol?
(c) Arrange the following in increasing order of acidity : Phenol, ethanol, water
11. (a) How can you obtain Phenol from
(i) Cumene (ii) Benzene sulphonic acid (iii) Benzene diazonium chloride?
(b) Write the structure of the major product obtained from dinitration of 3-methylphenol.
(c) Write the reaction involved in Kolbe’s reaction.
12. Arrange the following in increasing order of their acidic character :
Benzoic acid, Phenol, Cresol
13. What happens when
(a) Salicylic acid is treated with (CH3CO)2O/H+ ?

(b) Phenol is oxidised with Na2Cr2O7/H+?
(c) Anisole is treated with CH3Cl/anhydrous AlCl3?
Write chemical equation in support of your answer.
14. Arrange the following in increasing order of their boiling point :
CH3CH2OH, CH3CHO, CH3 – O – CH3
(a) Phenol reacts with Conc. HNO3?
(b) Ethyl chloride reacts with NaOC2H5?
16. (a) Butan-1-ol has a higher boiling point than diethyl ether. Why?
(b) An aromatic compound ‘A’ on treatment with CHCl3 and KOH gives two compounds, both of
which give same product ‘B’ when distilled with Zinc dust.Oxidation of ‘B’ gives ‘C’ with molecular
formula C7H6O2. Sodium salt of ‘C’ on heating with soda lime gives ‘D’ which may also be obtained by
distilling ‘A’ with Zinc dust. Identify ‘A’, ‘B’, ‘C’ and ‘D’.
17. 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
18. Write the structures of the products when Butan-2-ol reacts with the following :
(a) CrO3
(b) SOCl2
19. (a) Write the formula of reagents used in the following reactions :
(i) Bromination of phenol to 2,4,6-tribromophenol
(ii) Hydroboration of propene and then oxidation to propanol.
(b) Arrange the following compound groups in the increasing order of their property
indicated :
(i) p-nitrophenol, ethanol, phenol (acidic character)
(ii) Propanol, Propane, Propanal (boiling point)
(a) (CH3)3C – OH is treated with Cu at 573 K

(b) Anisole is treated with CH3Cl / anhydrous AlCl3
(c) Phenol is treated with Zn dust?
21. Give reason for the following:
(i) Phenol is more acidic than methanol.
(ii) The C-O-H bond angle in alcohols is slightly less than the tetrahedral angle
(iii) (𝑪𝑯𝟑)3C− 𝑶 − 𝑪𝑯𝟑 on reaction with HI gives (𝑪𝑯𝟑)𝟑𝑪 − 𝑰 𝒂𝒏𝒅 𝑪𝑯𝟑 − 𝑶𝑯 as the main
products and not (𝑪𝑯𝟑)𝟑 𝑪 − 𝑶𝑯 and 𝑪𝑯𝟑 − 𝑰.
22. (a) How do you convert the following:
(i) Phenol to anisole
(ii) Propan-2-ol to 2-methylpropan-2-ol
(iii) Aniline to phenol
23. How would you convert ethanol to ethene?
24. How would you obtain the following:
(i) Benzoquinone from phenol
(ii) 2-Methylpropan-2-ol from methyl magnesium bromide
(iii) Propan-2-ol from propene
25. Name the reagents used in the following reactions:
(i) Benzyl alcohol to benzoic acid.
(ii) Dehydration of propan-2-ol to propene.
(iii) Butan-2-one to butan-2-ol.
-----------------------------------------------------------------------------------------------

Worksheet On Alcoholss, Phenols and Ethers

Uploaded by

Copyright:

Available Formats

Worksheet On Alcoholss, Phenols and Ethers

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Worksheet On Alcoholss, Phenols and Ethers

Uploaded by

Copyright:

Available Formats

WORKSHEET ON ALCOHOLS, PHENOLS AND ETHERS

(b) Carry out the following conversions :

(i) Phenol to Salicylaldehyde

(ii) t-butylchloride to t-butyl ethyl ether

(iii) Propene to Propanol

(i) Phenol to benzoquinone

(ii) Anisole to p-bromoanisole

(iii) Phenol to 2,4,6-tribromophenol

3. Give reasons for the following :

4. (a) How can you convert the following :

(i) Sodium phenoxide to o-hydroxybenzoic acid

(ii) Acetone to propene

(iii) Phenol to chlorobenzene

(b) Write the preparation of phenol from cumene.

5. Write the equation for the preparation of 2-methyl-2-methoxypropane by Williamson synthesis.

(i) Hydroboration of propene followed by oxidation with H2O2 in alkaline medium.

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

7. How can you convert the following?

(i) Phenol to o-hydroxybenzaldehyde.

(ii) Methanal to ethanol

8. (a) How do you convert the following :

(i) Phenol to Anisole

(ii) Ethanol to Propan-2-ol

9. (a) Account for the following :

(i) o-nitrophenol is more steam volatile than p-nitrophenol.

(b) Write the reaction involved in the following :

(i) Reimer-Tiemann reaction

(ii) Friedal-Crafts Alkylation of Phenol

10. (a) Give equations of the following reactions :

(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.

(b) How will you distinguish between butan-1-ol and butan-2-ol?

11. (a) How can you obtain Phenol from

(c) Write the reaction involved in Kolbe’s reaction.

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

Benzoic acid, Phenol, Cresol

13. What happens when

(a) Salicylic acid is treated with (CH3CO)2O/H+ ?

(c) Anisole is treated with CH3Cl/anhydrous AlCl3?

Write chemical equation in support of your answer.

14. Arrange the following in increasing order of their boiling point :

CH3CH2OH, CH3CHO, CH3 – O – CH3

15. What happens when

(a) Phenol reacts with Conc. HNO3?

(b) Ethyl chloride reacts with NaOC2H5?

17. 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

(i) Bromination of phenol to 2,4,6-tribromophenol

(ii) Hydroboration of propene and then oxidation to propanol.

(i) p-nitrophenol, ethanol, phenol (acidic character)

(ii) Propanol, Propane, Propanal (boiling point)

20. What happens when

(a) (CH3)3C – OH is treated with Cu at 573 K

(c) Phenol is treated with Zn dust?

21. Give reason for the following:

(i) Phenol is more acidic than methanol.