Alcohols, Phenols and Ethers work sheet

Classification and Nomenclature:

1. Write the IUPAC name of the following compound. CH 3CH = CH - CH - CH2 - CH 3

OH

2. Give IUPAC name of the following compound. CH2 = CH - CH - CH2 - CH2 - CH3
OH

3. Write the IUPAC name of

CH3 - CH - CH2 - CH - CH - CH2OH

CH 3 OH CH 3

4. Write the IUPAC name of the following

CH 3

OH

CH 3
5. Write the IUPAC name of CH 3 - O - CH 2 - CH - CH 2 - CH3
CH 3

6. Draw the structure of hex 1 en 3 ol compound.

7. Draw the structural formula of 2 methylpropan 2 ol molecule.

8. Draw the structure of 2, 6 dimethyl phenol.

9. Write the structure of the molecule of compound whose IUPAC name is 1 phenyl propan 2-ol.

10. Write the structure of the following compound 2 methyl 2 ethoxypentane.

Theory:

1. The bond angle in alcohols is slightly less than the tetrahedral angle. Explain
 Alcohols, Phenols and Ethers work sheet

2. The bond angle in ethers is slightly more than the tetrahedral angle. Explain

3. What is meant by hydroboration-oxidation reaction? Illustrate it with an example

4. Arrange the following sets of compounds in order of their increasing boiling points:

(a) Pentan-1-ol, butan-1-ol, butan-2-ol, ethanol, propan-1-ol, methanol.

(b) Pentan-1-ol, n-butane, pentanal, ethoxyethane.

5. Arrange the following compounds in increasing order of their acid strength:

Propan-1-ol, 2,4,6-trinitrophenol, 3-nitrophenol, 3,5-dinitrophenol,
phenol, 4-methylphenol.

6. Of the two hydroxyl organic compounds ROH and ROH, the first one is basic and other is acidic in
behavior. How is R different from R?

7. o-nitrophenol has lower boiling point than p-nitrophenol. Explain.

8. Write the chemical equation for the preparation of phenol from benzene using oleum and sodium
hydroxide.

9. Explain the following behaviours.

 Alcohols, Phenols and Ethers work sheet
(i) Alcohols are more soluble in water than the hydrocarbons of comparable molecular masses.

(ii) Ortho nitrophenol is more acidic than ortho methoxyphenol.

10. Account for the following: Propanol has higher boiling point than butane.

11. Account for the following:

(i) The boiling points of alcohols decrease with increase in branching of the alkyl chain.

(ii) (ii) Phenol does not give protonation reaction readily.

12. Give one chemical test to distinguish between the following pairs of compounds.
(i) Phenol and benzoic acid (ii) 1 propanol and 2 propanol

13. Give reason for the following.

(i) m Amino phenol is a stronger acid than o amino phenol.

(ii) Alcohols act as weak bases.

14. Account for the following

(i) The boiling point of ethanol is higher than that of methanol.

(ii) Phenol is a stronger acid than an alcohol.

 Alcohols, Phenols and Ethers work sheet

(iii) Propanol has higher boiling point than butane.

15. Explain the following observations.

(i) The boiling point of ethanol is higher than of methoxy methane.

(ii) o and p nitro phenols are more acidic than phenol.

(iii) Why do phenols not give the protonation reaction readily?

16. Describe the chemical test to distinguish between ethanol and phenol

17. Why is the preparation of ether by acid catalysed dehydration of secondary alcohol not a suitable
method?

18. Phenyl methyl ether reacts with HI to give phenol and methyl iodide and not iodo benzene and
methyl alcohol. Why?
 Alcohols, Phenols and Ethers work sheet

19. The boiling points of ethers are lower than isomeric alcohols. Explain

20. Give the equations of reactions for the

(i) Preparation of phenol from cumene.

(ii) Preparation of phenol from chlorobenzene.

(iii) You are given benzene, conc. H2SO4 and NaOH. Write the equations for the preparation of
phenol using these reagents.

21. While separating a mixture of ortho and para nitrophenols by steam distillation, name the isomer
which will be steam volatile. Give reason.

22. Give two reactions that show the acidic nature of phenol. Compare acidity of phenol with that of
ethanol

23. Explain how does the OH group attached to a carbon of benzene ring activate it towards
electrophilic substitution?
 Alcohols, Phenols and Ethers work sheet
Named Reactions:

1. Write the equations involved in the following reaction: Reimer Tiemann reaction.

2. Write Reimer Tiemann reaction giving an example.

3. Write Kolbes reaction with an example

4. Illustrate the following reaction by giving a chemical equation. Williamsons synthesis

5. Write the equation involved in the reaction Williamsons ether synthesis.

Mechanism related:

1. Explain the mechanism of the following reaction? CH 3 CH 2 OH
H 2
CH 2
CH H 2O
443 K

(Or)
Describe the mechanism of acid catalysed dehydration of ethanol to yield ethene.

2. Describe the mechanism of hydration of ethene to yield ethanol (Or) Explain the mechanism of acid
catalyzed hydration of an alkene to form corresponding alcohol.
 Alcohols, Phenols and Ethers work sheet

3. Describe the mechanism of alcohols reacting both as nucleophiles and as electrophiles in their
reactions.

4. Explain the mechanism of the following reaction.

Addition of Grignards reagent to the carbonyl group of compound forming an adduct followed by
hydrolysis.

5. Give mechanism of preparation of ethoxy ethane from ethanol?

6. How is 1-propoxypropane synthesised from propan-1-ol? Write mechanism of this reaction.

 Alcohols, Phenols and Ethers work sheet
7. Write the mechanism of the reaction of HI with methoxymethane.

8. When 3-methylbutan-2-ol is treated with HBr, the following reaction takes place:

Give a mechanism for this reaction.

Completing Reactions:
9. Complete the following reaction equations.

(i) OH + SOCl2

CH2 OH

+ HCl
(ii)
OH

10. State the products of the following reactions.

 Alcohols, Phenols and Ethers work sheet
(i) CH3CH2CH2OCH3+HBr

OC 2H 5

+ HBr
(ii)

HI
(iii) (CH3)3C - OC2H 5

11.

12.

Conversions:
1. How is toluene obtained from phenol?
 Alcohols, Phenols and Ethers work sheet

2. How could you convert ethanol to ethene?

3. How will you convert the following?

(i) Propan 2 ol to propanone (ii) Phenol to 2,4,6 tribromophenol

4. How will you convert

(i) Propene to propan 1 ol (ii) Ethanal to propan 2 ol

5. How will you convert

(i) Propene to propan 2 ol? (ii )Phenol to 2,4,6 trinitrophenol?

6. How would you obtain

(i) Picric acid from phenol? (ii) 2 methyl propanol from 2 methyl propane?

7. How are the following conversions carried out?

(i) Benzyl chloride to benzyl alcohol

(ii) Methyl magnesium bromide to 2 methyl propane 2 ol.

(iii) Propene to propan 2 ol

(iv) Ethyl magnesium chloride to propan 1 ol.

 Alcohols, Phenols and Ethers work sheet
8. Draw the structure and name the product formed if the following alcohols are oxidized. Assume that
an excess of oxidizing agent is used.
(i)CH3CH2CH2CH2OH (ii)2 butanol (iii)2 methyl 1 propanol

9. 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

(iv) Propanone to 2 methylpropan -2 ol

(v) Propene to propan 2 ol

10. Name the reagents which are used in the following conservations.

(i) A primary alcohol to an aldehyde

(ii) Butan 2 one to butan 2 ol

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

 Alcohols, Phenols and Ethers work sheet
11. Name the reagents and write the chemical equation for the preparation of the following compounds
by Williamsons synthesis.
(a) Ethoxy benzene
(b) 2 methyl 2 methoxy propane

12.

13.

14.
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15.

16.

17.

18.
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19.

20.

21.
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22.

23.