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What is the principal product formed in the following sequence? R–C≡N (i) AlH(i-Bu)2 (ii) H2O

1. RCOOH
2. RCONH2
3. RCHO
4. RCH2NH2

Correct answer: RCHO

Solution

DIBAL-H (AlH(i-Bu)2) delivers one hydride to the nitrile to give an imine-aluminium intermediate; aqueous work-up hydrolyses it to the aldehyde. Hence R-C#N -> R-CHO.

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