Write a mechanism for the formation of semicarbazone Y

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.48P
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a) Write a mechanism for the formation of semicarbazone Y.

b) Explain why formation of imine Z is not favoured.

Semicarbazones are known to have biological activity against many common species of bacteria.
Semicarbazone Y can be prepared by reacting acetone with semicarbazide X. However, in this
reaction, imine Z will not form.
+
H2N,
H3C
H3C
`CH3
`NH2
`NH2
H
CH3 H
Semicarbazide, X
Semicarbazone, Y
CH3
H2N~N°
CH3
Imine, Z
Transcribed Image Text:Semicarbazones are known to have biological activity against many common species of bacteria. Semicarbazone Y can be prepared by reacting acetone with semicarbazide X. However, in this reaction, imine Z will not form. + H2N, H3C H3C `CH3 `NH2 `NH2 H CH3 H Semicarbazide, X Semicarbazone, Y CH3 H2N~N° CH3 Imine, Z
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