JEE Main 2021 · 26 August · evening · Single correct · +4 / −1

Consider the given reaction, identify 'X' and 'Y' :

JEE Main PYQ figure
  1. (a)
    Option (a)
  2. (b)
    Option (b)
  3. (c)
    Option (c)
  4. (d)
    Option (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.

  1. 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⁻.
  2. 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.
  3. 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

    OptionXYVerdict
    (a)NaOH, correctNH₂ and OH on one carbon, only 5 Cwrong Y
    (b)HNO₃, wrong1-amino-3-methylpentan-2-olwrong X
    (c)NaOH, correct1-amino-3-methylpentan-2-olboth correct
    (d)HNO₃, wrongNH₂ and OH on one carbon, only 5 Cboth wrong
  4. 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.

Study Aldehydes & Ketones

Asked about 130 times in JEE Main since 2020. This question is from 2021.