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JEE Advanced 2026Paper 1
Exam
JEE Advanced
Year
2026
Paper
Paper 1
Subject
Chemistry
Chapter
Alcohols Phenols and Ethers

JEE Advanced 2026 · Paper 1 · Chemistry · Alcohols Phenols and Ethers

Considering LiBH_4 reduces an ester group to the corresponding...

Considering LiBH4\text{LiBH}_4 reduces an ester group to the corresponding alcohol and does not reduce a carboxylic acid group, the correct statement about the major products P\textbf{P}, Q\textbf{Q}, R\textbf{R} and S\textbf{S} is

Considering LiBH_4 reduces an ester group to the corresponding alcohol and does not reduce a carboxylic acid group, the

Options

  1. AP\textbf{P} & Q\textbf{Q} are identical, and R\textbf{R} & S\textbf{S} are diastereomers.
  2. BP\textbf{P} & Q\textbf{Q} are diastereomers, and R\textbf{R} & S\textbf{S} are identical.
  3. CP\textbf{P} & Q\textbf{Q} are diastereomers, and R\textbf{R} & S\textbf{S} are diastereomers.
  4. DP\textbf{P} & Q\textbf{Q} are identical, and R\textbf{R} & S\textbf{S} are identical.

Correct answer

C. P\textbf{P} & Q\textbf{Q} are diastereomers, and R\textbf{R} & S\textbf{S} are diastereomers.

Step-by-step solution

From the given statement, LiBH4LiBH_4 selectively reduces the ester group (−CO2Et-CO_2Et) to an alcohol (−CH2OH-CH_2OH) and leaves the carboxylic acid (−CO2H-CO_2H) unchanged.

Borane (BH3BH_3), on the other hand, is a well-known reagent for the chemoselective reduction of carboxylic acids to alcohols in the presence of esters.

Let us analyze the first set of reactions yielding P and Q:
The starting material is a 1,2-disubstituted cyclobutane derivative. At C1, the ester group (−CO2Et-CO_2Et) is on a wedge (up) and the acid group (−CO2H-CO_2H) is on a dash (down). The adjacent C2 has a methyl group.
In product P (using LiBH4LiBH_4), the wedge −CO2Et-CO_2Et is reduced. Thus, the new −CH2OH-CH_2OH group is on the wedge.
In product Q (using BH3BH_3), the dash −CO2H-CO_2H is reduced. Thus, the new −CH2OH-CH_2OH group is on the dash.
Comparing P and Q, the stereocenter at C1 is inverted relative to the unchanged stereocenter at C2. Since their relative stereochemistry (cis vs trans relationship between −CH2OH-CH_2OH and −CH3-CH_3) is different, P and Q are diastereomers.

Now let us analyze the second set of reactions yielding R and S:
The starting material is a 1,3-disubstituted cyclobutane derivative. At C1, −CO2Et-CO_2Et is on a wedge and −CO2H-CO_2H is on a dash. At C3, there is a methyl group.
In product R (using LiBH4LiBH_4), the ester on the wedge is reduced. The resulting −CH2OH-CH_2OH group is on the wedge (cis to the methyl group if we assume methyl is up).
In product S (using BH3BH_3), the acid on the dash is reduced. The resulting −CH2OH-CH_2OH group is on the dash (trans to the methyl group).
Since R and S represent the cis and trans isomers of a 1,3-disubstituted cycloalkane, they are stereoisomers that are not mirror images. Therefore, R and S are also diastereomers.

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