Chapter 11

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

Explain why is ortho nitrophenol more acidic than ortho methoxyphenol ?

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

Give equations of the following reactions: (i) Oxidation of propan-1-ol with alkaline \(\mathrm{KMnO}_{4}\) solution. (ii) Bromine in \(\mathrm{CS}_{2}\) with phenol. (iii) Dilute \(\mathrm{HNO}_{3}\) with phenol. (iv) Treating phenol wih chloroform in presence of aqueous \(\mathrm{NaOH}\).

Explain the following with an example. (i) Kolbe's reaction. (ii) Reimer-Tiemann reaction. (iii) Williamson ether synthesis. (iv) Unsymmetrical ether.

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.

Give reason for the higher boiling point of ethanol in comparison to methoxymethane.

Give IUPAC names of the following ethers: (i) CCOCC(C)C (ii) \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{2} \mathrm{Cl}\) (iii) \(\mathrm{O}_{2} \mathrm{~N}-\mathrm{C}_{6} \mathrm{H}_{4}-\mathrm{OCH}_{3}(p)\) (iv) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OCH}_{3}\) (v) CCOC1CCC(C)(C)CC1 (vi) CCOc1ccccc1

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

Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable method. Give reason.