The carbonyl stretch of acetyl chloride (CH3COCI) is found at 1806 cm-1. Is the C=0 bond stronger or weaker thanthe one in an amide? What does this suggest about the resonance contribution of a lone pair on Cl in an acid chloridecompared to that of the lone pair on N in an amide? Explain. Hint: See Problems 15.43 and 15.44. Problem 15.43 calls attention to a resonance structure of an amide that accounts for the lowering of the C=0 stretchfrequency. An analogous resonance structure can be drawn for an ester. (a) Draw that resonance structure for methylacetate (CH3CO,CH3). (b) Based on the fact that an ester's c=0 stretch frequency is higher than an amide's, does thatresonance structure have a larger contribution toward the resonance hybrid of an ester or an amide? Using arguments ofcharge stability, explain why that should be so.

The stretching frequency of a compound is given by the expression v=12πkμ where k is the force…

Answered: The carbonyl stretch of acetyl chloride…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy

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Problem 56GP: Long-range coupling between protons more than two carbon atoms apart is sometimes observed when ...

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