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Explain why direct synthesis of benzoic acid to 4-bromobenzoic acid is not a viable option.

Explain why direct synthesis of benzoic acid to 4-bromobenzoic acid is not a viable option.

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Answer #1

-COOH is an aromatic ring deactivating group (m-directing). Br2/FeBr3 is the brominating agent of the benzene ring. The mechanism is shown below. C atom of benzene ring acts as a nucleophile here.

When -COOH group is present, it decreases the electron density of the benzene ring (nucleophilicity of the benzene ring decreases). Bromination of benzoic acid at p-position is difficult. The main product will be m-bromobenzoic acid.

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