Question Details

Considering LiBH4 reduces an ester group to the corresponding alcohol and does not reduce a carboxylic acid group, the correct statement about the major products P, Q, R and S is

Options

A

P & Q are identical, and R & S are diastereomers.

B

P & Q are diastereomers, and R & S are identical.

C

P & Q are diastereomers, and R & S are diastereomers.

D

P & Q are identical, and R & S are identical.

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Correct Answer :

Option A

P & Q are identical, and R & S are diastereomers.

Solution :

Correct Answer: P & Q are identical, and R & S are diastereomers.

To determine the stereochemical relationship between the major products P, Q, R, and S, we analyze the chemoselectivity of the reducing agent Lithium Borohydride (LiBH4) along with the symmetry and configuration of the resulting compounds.

Step 1: Chemoselectivity of LiBH4
Lithium borohydride (LiBH4) is a selective reducing agent. As given:
1. It selectively reduces an ester group (-COOR) to a primary alcohol (-CH2OH).
2. It does not reduce a carboxylic acid group (-COOH).

Step 2: Analysis of Products P and Q
When cyclic or acyclic stereoisomers containing both an ester group and a carboxylic acid group undergo reduction by LiBH4, only the ester group undergoes conversion to -CH2OH, while the -COOH group remains unchanged.

For the pair of reactions forming products P and Q:
• In P and Q, the reduction yields compounds where one substituent is -COOH and the other converted substituent is -CH2OH.
• Because the resulting functional groups at the two stereocenters/positions are identical (-CH2OH and -COOH swapped depending on orientation/rotation), rotating or flipping the molecule reveals a plane of symmetry or superimposability.
• Thus, P and Q represent the same chemical entity in different spatial orientations, making P & Q identical.

Step 3: Analysis of Products R and S
For the pair of products R and S:
• The relative stereocenters (cis vs. trans orientations of the substituents) remain fixed during the reaction because the reduction of the ester group occurs without inversion or retention affecting the stereogenic carbon backbone.
• One product pair retains a cis-relationship between substituents, while the other retains a trans-relationship.
• Non-superimposable stereoisomers that are not mirror images of each other are classified as diastereomers.
• Therefore, R & S are diastereomers.

Conclusion:
Combining both findings, P & Q are identical, and R & S are diastereomers.

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