JEE Main Chemistry question
Give the order of ease of the esterification of the following acids: (I) p-nitrobenzoic acid; (II) benzoic acid; (III) p-methylbenzoic acid; (IV) 2,4-dimethoxy-5-methylbenzoic acid (a sterically hindered, highly substituted acid).
Answer: (A)
Solution
Fischer esterification rate depends on the electrophilicity of the carbonyl carbon (favoured by electron-withdrawing substituents, which make the carbonyl more electrophilic toward the nucleophilic alcohol) and on steric accessibility (bulky ortho-type substituents hinder approach). p-Nitrobenzoic acid (I,
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