Consider the above reaction and predict the major product.
(A)(see structure)✓ Correct
(B)(see structure)
(C)(see structure)
(D)(see structure)
Answer: (A)
Solution
The reaction involves DiBAL-H (diisobutylaluminum hydride) reduction followed by hydrolysis. DiBAL-H is a selective reducing agent that reduces esters to aldehydes and nitriles to aldehydes (via imine intermediate). In this case, the ester group (−COOC2H5) is reduced to an aldehyde (−CHO), and the nitrile group (−CN) is also reduced to an aldehyde. The product contains two aldehyde groups as shown in option (A).
JEE Main · 2022 · 26 Jul 2022 · Shift 2 · Single correct option