Imine hydrolysis is rapid under strongly acidic conditions (H2O,1 equivalent HCI), but imine formation is slow under the same conditions. Provide a reasonable explanation for the observed reactivity. NH +H2O, 1 eq. HCI NH3 FAST NH -H20, 1 eq. HCI NH3 SLOW

Imine hydrolysis is rapid under strongly acidic conditions (H2O,1 equivalent HCI), but imine formation is slow under the same conditions. Provide a reasonable explanation for the observed reactivity. NH +H2O, 1 eq. HCI NH3 FAST NH -H20, 1 eq. HCI NH3 SLOW

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

Chapter23: Amines

Section: Chapter Questions

Problem 23.29P

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Aldehydes and Ketones

Aldehydes and ketones are organic compounds that have a carbonyl group, C = O, as their functional group. They both differ in the placement of this carbonyl group in their structures.

Question

Imine hydrolysis is rapid under strongly acidic conditions (H2O, 1 equivalent HCI), but imine
formation is slow under the same conditions. Provide a reasonable explanation for the
observed reactivity.
NH
+H2O, 1 eq. HCI
NH3
FAST
NH
-H20, 1 eq. HCI
NH3
SLOW

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