Question
Write a note on esterification of alcohols and phenols.
✓
Answer
$\rightarrow$ Alcohols and phenols react with carboxylic acids, acid chlorides and acid anhydrides to form esters.
$Ar / RO - H + R ^{\prime}- COOH \stackrel{ H ^{+}}{\rightleftharpoons} Ar / ROCOR ^{\prime}+ H _2 O$
$Ar / R - OH +\left( R ^{\prime} CO \right)_2 O \stackrel{ H ^{+}}{\rightleftharpoons} Ar / ROCOR '+ R ^{\prime} COOH$
$R / ArOH + R ^{\prime} COCl \xrightarrow{\text { Pyridine }} R / ArOCOR ' + HCl$
$\rightarrow$ The reaction with carboxylic acid and acid anhydride is carried out in the presence of a small amount of concentrated sulphuric acid. The reaction is reversible, and therefore, water is removed as soon as it is formed. The reaction with acid chloride is carried out in the presence of a base $($pyridine$)$ so as to neutralise $ \text{HCl}$ which is formed during the reaction. It shifts the equilibrium to the right hand side. The introduction of acetyl $(CH_3CO)$ group in alcohols or phenols is known as acetylation. Acetylation of salicylic acid produces aspirin.
$Ar / RO - H + R ^{\prime}- COOH \stackrel{ H ^{+}}{\rightleftharpoons} Ar / ROCOR ^{\prime}+ H _2 O$
$Ar / R - OH +\left( R ^{\prime} CO \right)_2 O \stackrel{ H ^{+}}{\rightleftharpoons} Ar / ROCOR '+ R ^{\prime} COOH$
$R / ArOH + R ^{\prime} COCl \xrightarrow{\text { Pyridine }} R / ArOCOR ' + HCl$
$\rightarrow$ The reaction with carboxylic acid and acid anhydride is carried out in the presence of a small amount of concentrated sulphuric acid. The reaction is reversible, and therefore, water is removed as soon as it is formed. The reaction with acid chloride is carried out in the presence of a base $($pyridine$)$ so as to neutralise $ \text{HCl}$ which is formed during the reaction. It shifts the equilibrium to the right hand side. The introduction of acetyl $(CH_3CO)$ group in alcohols or phenols is known as acetylation. Acetylation of salicylic acid produces aspirin.
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