How are reactions of aldehydes and nucleophiles fundamentally different than the reaction between acyl chlorides and nucleophiles?
A
Aldehydes are readily oxidized by nucleophile to carboxylic acid.
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B
Acyl chloride has a leaving group Cl− whereas aldehyde does not.
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C
Aldehyde do not form tetrahedral intermediate with nucleophile.
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D
Acyl chloride readily forms enol tautomer.
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Solution
The correct option is D Acyl chloride has a leaving group Cl− whereas aldehyde does not. Acyl chloride undergo nucleophilic substitution while aldehydes undergo nucleophilic addition as shown above :