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JEE Advanced2026Paper 1CHEM-I
Q.

Considering LiBH reduces an ester group to the corresponding alcohol and does not reduce a carboxylic acid group, the correct statement about the major products , , and is

  1. A

    & are identical, and & are diastereomers.

  2. B

    & are diastereomers, and & are identical.

  3. C

    & are diastereomers, and & are diastereomers.

  4. D

    & are identical, and & are identical.

Solution

Reagent selectivity. LiBH selectively reduces the ester (–COEt –CHOH) and leaves the carboxylic acid intact. BH behaves oppositely on this substrate: it preferentially reduces the carboxylic acid (–COH –CHOH) and leaves the ester intact.

Lactonisation under acidic workup. In each case the resulting hydroxy-acid (or hydroxy-ester) undergoes intramolecular cyclisation to form a five-membered lactone. The lactone is formed with retention of the existing stereocentres on the ring carbon.

Top substrate. Starting from one diastereomer:

  • With LiBH then H: ester reduces to CHOH, then the CHOH cyclises onto the carboxylic acid, giving lactone .
  • With BH then H: carboxylic acid reduces to CHOH, then the CHOH cyclises onto the ester, giving lactone .

and both contain the same skeleton but the relative orientation of the CH substituent versus the lactone oxygen/carbonyl differs because the new CHO and C=O attachments are swapped at the ring carbon. They are therefore diastereomers.

Bottom substrate (opposite stereochemistry of the substituted ring carbon). The same argument applies: and are also diastereomers, differing in which of the two CHO / C=O ends is attached at the ring carbon.

Hence & are diastereomers and & are diastereomers. Option (C).

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