Among the following compounds, which will react with acetone to give a product containing > C = N - bond?
(IIT-JEE, 1998)

C_{6} H_{5} N H_{2}

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(C H_{3})_{3} N

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C_{6} H_{5} N H C_{6} H_{5}

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C_{6} H_{5} N H N H_{2}

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Solution

The correct option is D $C_{6} H_{5} N H N H_{2}$
Here, amines act as nucleophiles. Important thing to note is that the bond being asked for is an imine bond and can be only formed when a primary amine reacts with this ketone.
If you keep this in mind then it is quite straightforward from here. The following compounds can be formed with the imine bond:
$(a) P h N H_{2} + O = C (C H_{3})_{2} \to P h N = C (C H_{3})_{2}$
$(a) P h N H N H_{2} + O = C (C H_{3})_{2} \to P h N H N = C (C H_{3})_{2}$

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C_{6} H_{5} N H_{2}, (C H_{3})_{3} N, C_{6} H_{5} N H C_{6} H_{5}, C_{6} H_{5} N H N H_{2}

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