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The Cannizaro Reaction

Benzoic acid ...

Question

Benzoic acid is treated with ${SOCl}_{2}$ and the product X formed is reacted with ammonia to give Y. Y on reaction with ${Br}_{2}$ and $KOH$ gives Z. What is Z in the reaction?

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Solution

Additionally, the benzoic acid interacts with thionyl chloride ( ${SOCl}_{2}$ ) to produce benzoyl chloride, which is then reduced with either $H_{2} / Pd$ or ${BaSO}_{4}$ to produce benzaldehyde (Rosenmund reduction).
When toluene and ${KMnO}_{4}$ are combined, benzoic acid is produced.
Alkyl to carboxylic conversion occurs in toluene during this exchange.
Therefore in this reaction, Z is aniline.

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