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Which of the following reactions will NOT give primary amine as the product?
A
$CH_3CONH_2\xrightarrow[(ii)\ H_3O^{\oplus}]{(i)\ LiAlH_4}$ Product
B
$CH_3CONH_2\xrightarrow{Br_2/KOH}$ Product
C
$CH_3CN\xrightarrow[(ii)\ H_3O^{\oplus}]{(i)\ LiAlH_4}$ Product
D
$CH_3NC\xrightarrow[(ii)\ H_3O^{\oplus}]{(i)\ LiAlH_4}$ Product
Explanation
$CH_3NC$ on reduction gives the secondary amine $CH_3NHCH_3$.
Detailed Solution
$CH_3CONH_2\xrightarrow[(ii)\ H_3O^{\oplus}]{(i)\ LiAlH_4}CH_3CH_2NH_2$
$CH_3CONH_2\xrightarrow{Br_2/KOH}CH_3NH_2$
$CH_3CN\xrightarrow[(ii)\ H_3O^{\oplus}]{(i)\ LiAlH_4}CH_3CH_2NH_2$
$CH_3NC\xrightarrow[(ii)\ H_3O^{\oplus}]{(i)\ LiAlH_4}CH_3NHCH_3$
Methyl isocyanide gives a secondary amine, $CH_3NHCH_3$, upon reduction.