Aldehydes and ketones

Introducing reactions of aldehydes and ketones.

Benzaldehyde reacts with methylenetriphenylphosphorane:

Steps:

1. α-H of phosphonium salt is abstracted by tert-butyloxy anion, forming a phosphonium ylide;
2. Stepwise cycloaddition occurs between phosphonium ylide and the carbonyl group of benzaldehyde, generating a four-membered ring intermediate;
3. The four-membered ring breaks to form styrene and triphenylphosphine oxide.

Baeyer–Villiger oxidation of methylcyclohexanone:

Steps:

1. The carbonyl group in methylcyclohexanone is protonated;
2. Hydroxyl group in the peracid undergoes nucleophilic addition to the protonated carbonyl;
3. Alkyl migration occurs, and then a carboxylate is eliminated;
4. Proton on carbonyl group dissociates, producing an oxygen-inserted product.

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