Which of the following reactions will NOT give primary amine as the product?
- CH3CN [ (ii) H3O ](i) LiAlH4 Product
- CH3NC [ (ii) H3O ](i) LiAlH4 Product
- CH3CONH2 [ (ii) H3O ](i) LiAlH4 Product
- CH3CONH2 Br2/KOH Product
Answer
(2) CH3NC [ (ii) H3O ](i) LiAlH4 Product
Solution
(1) CH3C N LiAlH4 CH3CH2NH2 (primary amine)
(2) CH3N C LiAlH4 CH3NHCH3 (secondary amine): reduction of an isocyanide gives an N-methyl amine.
(3) CH3CONH2 LiAlH4 CH3CH2NH2 (primary amine)
(4) CH3CONH2 Br2/KOH CH3NH2 (primary amine, Hoffmann bromamide degradation)
Only reaction (2) does not give a primary amine.
Answer: (2)