JEE Main 2022 · 26 June · evening · Single correct · +4 / −1
The reagent, from the following, which converts benzoic acid to benzaldehyde in one step is
- (a) LiAlH₄
- (b) KMnO₄
- (c) MnO
- (d) NaBH₄
Answer and solution
Answer (c) MnO
Solution
Chemistry ma’am · 3 steps
Acid to aldehyde is a reduction that must stop halfway, and only MnO stops it there.
- What is needed. The -COOH carbon must become a -CHO carbon. That is a reduction, and it has to stop at the aldehyde, which is itself easy to reduce or oxidise.
Reagent What it does to C₆H₅COOH Product LiAlH₄ Strong reducer, does not stop at the aldehyde C₆H₅CH₂OH KMnO₄ Oxidising agent, cannot reduce anything no change MnO, 573 K Catalyses a controlled reduction with formic acid C₆H₅CHO NaBH₄ Too mild to reduce a carboxylic acid no change - The MnO route. Pass vapours of the acid and formic acid over MnO at about 573 K. Formic acid supplies the hydrogen, and the aldehyde forms in one step.
C₆H₅COOH + HCOOH →(MnO, 573 K) C₆H₅CHO + CO₂ + H₂O
- So. The one-step reagent is MnO, option (c).
The idea to keep. Before picking a reagent, ask two things: is this an oxidation or a reduction, and does the reagent stop at the right stage? Aldehydes sit in the middle, so strong reagents run past them.
Answer from the NTA final answer key. Solution by PrepWiser.