Question 1

Classify the following as primary, secondary and tertiary alcohols:
(i)

(ii) CH₂C = CH - CH₂OH 
(iii) CH₃ - CH₂ - CH₂ - OH
(iv)

(v)

(vi)

Question 4
Show how are the following alcohols prepared by the reaction of a suitable
Grignard reagent on methanal?
(i)

(ii)

Question 5
Write structures of the products of the following reactions:
(i)

(ii)

(iii)

Question 7
Predict the major product of acid catalysed dehydration of
(i) 1-Methylcyclohexanol and
(ii) Butan-1-ol

Question 9
Write the equations involved in the following reactions:
(i) Reimer-Tiemann reaction
(ii) Kolbe's reaction

Question 11
Which of the following is an appropriate set of reactants for the preparation of 1-methoxy-4-nitrobenzene and why?

Question 1
Write IUPAC names of the following compounds:

Question 2
Write structures of the compounds whose IUPAC names are as follows:
(i) 2-Methylbutan-2-ol
(ii) 1-Phenylpropan-2-ol
(iii) 3,5-Dimethylhexane -1, 3, 5-triol
(iv) 2,3 - Diethylphenol
(v) 1 - Ethoxypropane
(vi) 2-Ethoxy-3-methylpentane
(vii) Cyclohexylmethanol
(viii) 3-Cyclohexylpentan-3-ol
(ix) Cyclopent-3-en-1-ol
(x) 3-Chloromethylpentan-1-ol.

Question 4
Explain why propanol has higher boiling point than that of the hydrocarbon, butane?

Question 6
What is meant by hydroboration-oxidation reaction? Illustrate it with an example.

Question 13
Show how will you synthesize:
(i) 1-phenylethanol from a suitable alkene.
(ii) cyclohexylmethanol using an alkyl halide by an S_N2 reaction.
(iii) pentan-1-ol using a suitable alkyl halide?

Question 15
Explain why is ortho nitrophenol more acidic than ortho methoxyphenol?

Question 16
Explain how does the -OH group attached to a carbon of benzene ring activate it towards electrophilic substitution?

Question 17
Give equations of the following reactions:
(i) Oxidation of propan-1-ol with alkaline KMnO₄ solution.
(ii) Bromine in CS₂ with phenol.
(iii) Dilute HNO₃ with phenol.
(iv) Treating phenol with chloroform in presence of aqueous NaOH.

Question 20
How are the following conversions carried out?
(i) Propene → Propan-2-ol
(ii) Benzyl chloride → Benzyl alcohol
(iii) Ethyl magnesium chloride → Propan-1-ol.
(iv) Methyl magnesium bromide → 2-Methylpropan-2-ol.

Question 21
Name the reagents used in the following reactions:
(i) Oxidation of a primary alcohol to carboxylic acid.
(ii) Oxidation of a primary alcohol to aldehyde.
(iii) Bromination of phenol to 2,4,6-tribromophenol.
(iv) Benzyl alcohol to benzoic acid.
(v) Dehydration of propan-2-ol to propene.
(vi) Butan-2-one to butan-2-ol.

Question 23
Give IUPAC names of the following ethers:

Question 24
Write the names of reagents and equations for the preparation of the following ethers by Williamson's synthesis:
(i) 1-Propoxypropane
(ii) Ethoxybenzene
(iii) 2-Methoxy-2-methylpropane
(iv) 1-Methoxyethane

Question 26
How is 1-propoxypropane synthesised from propan-1-ol? Write mechanism of this reaction.

Question 28
Write the equation of the reaction of hydrogen iodide with:
(i) 1-propoxypropane
(ii) Methoxybenzene and
(iii) Benzyl ethyl ether

Question 31
Write equations of the following reactions:
(i) Friedel-Crafts reaction-alkylation of anisole.
(ii) Nitration of anisole.
(iii) Bromination of anisole in ethanoic acid medium.
(iv) Friedel-Craft's acetylation of anisole.

Question 33
When 3-methylbutan-2-ol is treated with HBr, the following reaction takes place:

Give a mechanism for this reaction.
(Hint : The secondary carbocation formed in step II rearranges to a more stable tertiary carbocation by a hydride ion shift from 3rd carbon atom.