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Question

Account for the following:

(a) Aromatic carboxylic acids do not undergo Friedel-Crafts reaction.

(b) pKa  value of 4-nitrobenzoic acid is lower than that of benzoic acid.


Solution

(a) This is because the -COOH group is deactivating and the catalyst AlCl3 gets bonded to -COOH group.

(b) NO2 group is an electron withdrawing group owing to -I effect. So it stabilises the COO ion and strengthens the acid in 4-nitrobenzoic acid.

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