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Question

When semicarbazide reacts with a ketone(or aldehyde) to form semicarbazone. Only one nitrogen atom of semicarbazide acts as a nucleophile and attack the carbonyl carbon of the ketone. The product of the reaction consequently is R2C=NNHCONH2 rather than R2C=NCONHNH2. What factor account for the fact that two nitrogen atoms of semicarbazide are relatively non nucleophilic?

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Solution

There is no available lone pair on nitrogen atom in semicarbozone, i.e., why two nitrogen atoms of semicarbozide are relatively non- nucleophilic.
1175003_1023289_ans_cbdcb036b7934a3c900d5b989336fdd4.PNG

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