JEE Main 2023 · 10 April · evening · Single correct · +4 / −1

In the reaction given below:
The product 'X' is:

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

Answer (a)

Solution

Chemistry ma’am · 3 steps

Go group by group: LiAlH4 reduces the ketone and the amide, but it leaves the C=C alone.

  1. Spot the groups. The starting compound has three groups that could react: a ketone (C=O), a C=CH₂ double bond next to it, and a primary amide (-CONH₂).
    GroupWith LiAlH₄, then H₃O⁺In the product
    Ketone >C=OHydride adds to the carbonyl carbon and workup protonates the Osecondary alcohol >CH-OH
    Amide -CONH₂The carbonyl oxygen is removed completelyamine -CH₂NH₂
    Alkene >C=CH₂Hydride is a nucleophile and goes to the polar C=O, not to the C=Cstays as >C=CH₂
  2. Amide to amine. After the first hydride adds, the oxygen leaves bound to aluminium and an iminium ion forms. A second hydride reduces it, so that carbon ends up as CH₂ next to NH₂.
  3. So. X is CH₃CH₂CH(OH)-C(=CH₂)-CH(CH₃)-CH₂NH₂: an alcohol, an untouched C=CH₂, and an amine. That is option (a).

The idea to keep. LiAlH₄ turns ketones into alcohols and amides into amines, removing the amide oxygen fully. Its hydride attacks C=O groups, so a C=C usually survives.

Answer from the NTA final answer key. Solution by PrepWiser.

Study Amines & Diazonium Salts

Asked about 170 times in JEE Main since 2020. This question is from 2023.