JEE Main 2021 · 26 August · evening · Single correct · +4 / −1
Consider the given reaction, identify 'X' and 'Y' :
- (a)
- (b)
- (c)
- (d)
Answer and solution
Answer (c)
Solution
Chemistry ma’am · 4 steps
Base makes the cyanide ion that attacks the C=O, and LiAlH4 turns the C≡N into CH2NH2.
- Choosing X. HCN is a weak acid, so on its own it gives very little CN⁻. A base such as NaOH pulls off the proton and makes CN⁻, the nucleophile that attacks the carbonyl carbon. An acid like HNO₃ would push the equilibrium back and suppress CN⁻.
- Cyanohydrin forms. CN⁻ adds to the C=O carbon of 2-methylbutanal, and the alkoxide picks up H⁺ from water. This gives CH₃CH₂CH(CH₃)CH(OH)CN, which has 6 carbons because the CN brings one carbon in.
- Choosing Y. LiAlH₄ followed by H₃O⁺ adds four H atoms across the C≡N triple bond and turns it into CH₂NH₂. The OH group is not touched, and the nitrile carbon stays in the chain.
CH₃CH₂CH(CH₃)CH(OH)C≡N →(1. LiAlH₄, 2. H₃O⁺) CH₃CH₂CH(CH₃)CH(OH)CH₂NH₂
Option X Y Verdict (a) NaOH, correct NH₂ and OH on one carbon, only 5 C wrong Y (b) HNO₃, wrong 1-amino-3-methylpentan-2-ol wrong X (c) NaOH, correct 1-amino-3-methylpentan-2-ol both correct (d) HNO₃, wrong NH₂ and OH on one carbon, only 5 C both wrong - So. X is NaOH and Y is 1-amino-3-methylpentan-2-ol, CH₃CH₂CH(CH₃)CH(OH)CH₂NH₂. That is option (c).
The idea to keep. Cyanohydrin formation needs a base to generate CN⁻. Reducing a cyanohydrin with LiAlH₄ gives a 1,2-amino alcohol that keeps the extra carbon from CN.
Answer from the NTA final answer key. Solution by PrepWiser.