JEE Main 2023 · 10 April · evening · Single correct · +4 / −1
In the reaction given below:
The product 'X' is:
- (a)
- (b)
- (c)
- (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.
- 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).
Group With LiAlH₄, then H₃O⁺ In the product Ketone >C=O Hydride adds to the carbonyl carbon and workup protonates the O secondary alcohol >CH-OH Amide -CONH₂ The carbonyl oxygen is removed completely amine -CH₂NH₂ Alkene >C=CH₂ Hydride is a nucleophile and goes to the polar C=O, not to the C=C stays as >C=CH₂ - 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.
- 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.