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Which of the following reactions will NOT give primary amine as the product? (1) CH3CONH2→Br2/KOHProductCH_3CONH_2 \xrightarrow{Br_2/KOH} \text{Product} (2) CH3CN→(ii) H3O+(i) LiAlH4ProductCH_3CN \xrightarrow[\text{(ii) } H_3O^+]{\text{(i) } LiAlH_4} \text{Product} (3) CH3NC→(ii) H3O+(i) LiAlH4ProductCH_3NC \xrightarrow[\text{(ii) } H_3O^+]{\text{(i) } LiAlH_4} \text{Product} (4) CH3CONH2→(ii) H3O+(i) LiAlH4ProductCH_3CONH_2 \xrightarrow[\text{(ii) } H_3O^+]{\text{(i) } LiAlH_4} \text{Product}

A

(1)

B

(2)

C

(3)

D

(4)

Step-by-Step Solution

Reaction (1) is Hofmann bromamide degradation, which gives primary amine. Reaction (2) reduces nitrile to primary amine. Reaction (4) reduces amide to primary amine. Reaction (3) involves CH3NCCH_3NC (methyl isocyanide), which upon reduction with LiAlH4LiAlH_4 gives secondary amine (CH3NHCH3CH_3NHCH_3). Thus, (3) does not give a primary amine.

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