Which of the following do not give acetamide on reaction with $N H_{3}$ (No heating)

C H_{3} C O C l

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C H_{3} C O O C H_{3}

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(C H_{3} C O)_{2} O

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C H_{3} C O O H

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Solution

The correct option is D $C H_{3} C O O H$
The given sequnce of reactions is
$C H_{3} C O N H_{2} B r_{2} / K O H - ------- \to C H_{3} N H_{2} C_{6} H_{5} C O C l - ------- \to C H_{3} N H C O C_{6} H_{5}$
The first reaction is Hofmann bromamide degradation in which amide is converted to amine containing one carbon atom less.
The second reaction is schotten - Baumann in which amine reacts with acid chloride or acid anhydride to form an amide.

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