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How will you bring about the following conversions?
Anisole from phenol. Ethyl acetate from ethanol.
(i)[1.0]
Anisole from phenol.
(ii)[1.0]
Ethyl acetate from ethanol.
Answer
Answer (i)
AIEquations: $\mathrm{C_{6}H_{5}OH} + \mathrm{NaOH} \longrightarrow \mathrm{C_{6}H_{5}ONa} + \mathrm{H_{2}O}$ $\mathrm{C_{6}H_{5}ONa} + \mathrm{CH_{3}Cl} \xrightarrow{\text{heat}} \mathrm{C_{6}H_{5}OCH_{3}} + \mathrm{NaCl}$
Phenol is converted to sodium phenoxide with NaOH, which reacts with methyl chloride (Williamson synthesis) to give anisole.
Answer (ii)
AIEquation: $\mathrm{C_{2}H_{5}OH} + \mathrm{CH_{3}COOH} \xrightarrow{\text{conc.}\text{ }\mathrm{H_{2}SO_{4}}\text{,}\text{ }\text{heat}} \mathrm{CH_{3}COOC_{2}H_{5}} + \mathrm{H_{2}O}$
Ethanol is heated with ethanoic acid in the presence of conc. $\mathrm{H_2SO_4}$ (esterification) to give ethyl acetate.
From ISC 2018 Chemistry Paper 1, question 7(b).