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Suggest possible reaction mechanisms for the reaction of acetone and semicarbazide?
Wiki User
∙ 14y ago
Reaction: CH3C(=O)CH3 + NH2NHC(=O)NH2 --> (CH3)2C=NNHC(=O)NH2
1) N from NH2 acts as the nucleophile, attacks the carbonyl group and changes into a tetrahedral intermediate. Positive charge on NH2, negative charge on oxygen.
(CH3)2(O-C)--(NH2)+NHC(=O)NH2
2) oxygen takes the hydrogen from nitrogen through rearrangement because it is more electronegative.
(CH3)2(HOC)--(NH)NHC(=O)NH2
3) Acid protonates the alcohol once more to make it a better leaving group.
(CH3)2(H2O+C)--(NH)NHC(=O)NH2
4) Nitrogen from NH2 donates its electrons to generate a double bond, bumping off the water molecule and leaving a positive charge on nitrogen.
(CH3)2C=NH+NHC(=O)NH2
5) Water pulls off the hydrogen that was still attached to the nitrogen, thus generating the condensation product between acetone and semicarbazide.
(CH3)2C=NNHC(=O)NH2
Wiki User
∙ 14y ago
Hysam Hameda
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