Question Details

Identify the suitable reagent for the following conversion.


Options

A

(i) LiAlH4, (ii) H+/H2O

B

(i) AlH(iBu)2 (ii) H2O

C

(i) NaBH4, (ii) H+/H2O

D

H2/Pd-BaSO4

Show Answer

Correct Answer :

Option B

(i) AlH(iBu)2 (ii) H2O

(i) AlH(iBu)2, (ii) H2O

Solution :

The correct answer is (i) AlH(iBu)2, (ii) H2O.

Step-by-Step Explanation:

1. Identify the reactant and the product from the reaction scheme:
The given image shows the conversion of methyl benzoate (C6H5COOCH3) into benzaldehyde (C6H5CHO). This is a selective reduction of an ester to an aldehyde.

2. Analyze the reaction behavior of each given reagent:
LiAlH4 followed by H+/H2O: Lithium aluminium hydride is a very strong reducing agent. It reduces esters completely to primary alcohols (in this case, yielding benzyl alcohol, C6H5CH2OH), rather than stopping at the aldehyde stage.
NaBH4 followed by H+/H2O: Sodium borohydride is a mild reducing agent and is generally not reactive enough to reduce esters under standard conditions.
H2/Pd-BaSO4: This reagent combination (Rosenmund catalyst) is used to reduce acid chlorides to aldehydes, but it does not reduce esters to aldehydes.
AlH(iBu)2 (Diisobutylaluminium hydride, DIBAL-H) followed by H2O: DIBAL-H is a selective, bulky reducing agent. When reacted with an ester at low temperatures (typically around -78 °C), it adds one equivalent of hydride to the carbonyl carbon to form a stable tetrahedral hemiacetal-like intermediate. This intermediate does not undergo further reduction. Subsequent acidic hydrolysis with water decomposes the intermediate to yield the target aldehyde (benzaldehyde).

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