How to convert benzoic acid to benzaldehyde?

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Solution

Conversion of Benzoic acid to Benzaldehyde:-
Step 1: Formation of Benzoyl chloride
The Benzoic acid is treated with Thionyl chloride $({SOCl}_{2})$ to form Benzoyl chloride:
Step 2: Formation of Benzaldehyde
The Benzoyl chloride formed is now treated with Lindlar's catalyst $(H_{2} / Pd, {BaSO}_{4})$ and undergoes Rosenmund's reduction to form our required Benzaldehyde:
This conversion of Benzoic acid to Benzaldehyde is a 2 step reaction
Therefore, Benzoic acid when reacted with Thionyl chloride $({SOCl}_{2})$ then followed by Rosenmund's reduction produces Benzaldehyde.

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How will you bring about the following conversions in not more than two steps?

(i) Propanone to Propene

(ii) Benzoic acid to Benzaldehyde

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