Question
How will you convert carboxylic acids and esters to primary alcohols? Explain with suitable examples.
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Answer
Carboxylic acids and esters are not easily reduced by catalytic hydrogenation or by $NaBH_4.$ However, relatively more reactive and an expensive $LiAlH_4$ is used to convert carboxylic acids and esters to primary alcohols. When acetic acid is reduced in the presence of $LiAlH_4$ and followed by their acid hydrolysis, ethyl alcohol is obtained.
When ethyl acetate is reduced in the presence of $LiA _4 H _4$ and followed by their acid hydrolysis. $n$ propyl alcohol and ethyl alcohol is obtained.
[Since $LiA1H _4$ is an expensive reagent. commercially acids are reduced to alcohol by converting them to esters, followed by their reduction. $($catalytic hydrogenation$)$
$R - COOH \xrightarrow[ H ^{+}]{ R \ ^{\prime} OH } RCOOR \ ^{\prime} \xrightarrow[\text { Catalyst }]{ H _2} RCH _2 OH + R \ ^{\prime} OH$
When ethyl acetate is reduced in the presence of $LiA _4 H _4$ and followed by their acid hydrolysis. $n$ propyl alcohol and ethyl alcohol is obtained.
[Since $LiA1H _4$ is an expensive reagent. commercially acids are reduced to alcohol by converting them to esters, followed by their reduction. $($catalytic hydrogenation$)$
$R - COOH \xrightarrow[ H ^{+}]{ R \ ^{\prime} OH } RCOOR \ ^{\prime} \xrightarrow[\text { Catalyst }]{ H _2} RCH _2 OH + R \ ^{\prime} OH$
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