Predict the products of the following reactions:
(e)
(f)

Guida verificata passo dopo passo

Step 1: Analyze the reagent DIBAL-H (Diisobutylaluminum hydride). DIBAL-H is a selective reducing agent that reduces esters and lactones to aldehydes under controlled conditions (low temperature, -78°C). It does not reduce the carbonyl group completely to an alcohol in this case.

Step 2: For reaction (e), identify the functional groups in the starting material. The molecule contains an ester group (O=C-OCH₃) and a double bond in the alkyl chain. DIBAL-H selectively reduces the ester group to an aldehyde without affecting the double bond.

Step 3: For reaction (f), identify the functional groups in the starting material. The molecule contains a lactone (cyclic ester). DIBAL-H selectively reduces the lactone to an aldehyde, opening the ring structure in the process.

Step 4: Consider the reaction conditions. The reaction is performed at -78°C, which ensures selective reduction to aldehydes without over-reduction to alcohols. The addition of water (H₂O) in the second step quenches the reaction and hydrolyzes the aluminum complex formed during reduction.

Step 5: Predict the products. For reaction (e), the ester group is reduced to an aldehyde, and the double bond remains intact. For reaction (f), the lactone is reduced to an aldehyde, resulting in a linear molecule with an aldehyde group at one end.

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