NEST2026ChemistryAldehydes and Ketones
Consider the following compound. The compound undergoes reaction with two equivalents of diisobutyl aluminium hydride followed by acid hydrolysis to provide P as the major product. The structure of P is:
Correct answer
1
Step-by-step solution
The given compound contains an ester group ( - CO ₂ Et ), a nitrile group ( - CN ), and an isolated carbon-carbon double bond. Diisobutylaluminium hydride (DIBAL-H) is a selective reducing agent. When 2 equivalents of DIBAL-H are used followed by acid hydrolysis: 1. One equivalent reduces the ester group to an aldehyde ( - CHO ). 2. The second equivalent reduces the nitrile group to an imine intermediate, which upon acid hydrolysis yields an aldehyde ( - CHO ). 3. DIBAL-H does not reduce isolated C=C double bonds.