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Question

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

A
C6H5NH2
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B
(CH3)3N
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C
C6H5NHC6H5
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D
C6H5NHNH2
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Solution

The correct option is D C6H5NHNH2
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)PhNH2+O=C(CH3)2PhN=C(CH3)2
(a)PhNHNH2+O=C(CH3)2PhNHN=C(CH3)2

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