How do the following experimental results support the resonance description of the relativestability of acid chlorides compared to amides? The C-Cl bond lengths in CH3CI and CH;COCIare identical (178 pm), but the C-N bond in HCONH, is shorter than the C-N bond in CH;NH2(135 pm versus 147 pm).

The relative stability of acid chloride and amides have to be compared.

Answered: How do the following experimental…

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

Section23.9: Hofmann Elimination

Problem 23.14P

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How do the following experimental results support the resonance description of the relative stability of acid chlorides compared to amides? The C-Cl bond lengths in CH3CI and CH;COCI are identical (178 pm), but the C-N bond in HCONH, is shorter than the C-N bond in CH;NH2 (135 pm versus 147 pm).