Problem 15.43 calls attention to a resonance structure of an amide that accounts for the lowering of the C=0 stretch frequency. An analogous resonance structure can be drawn for an ester. (a) Draw that resonance structure for methyl acetate (CH3CO,CH3). (b) Based on the fact that an ester's c=0 stretch frequency is higher than an amide's, does that resonance structure have a larger contribution toward the resonance hybrid of an ester or an amide? Using arguments of charge stability, explain why that should be so. In Section 15.5c, we learned that the frequency of the C=0 stretch for an amide is lower than it is for a ketone, suggesting that the C=0 bond is weaker in an amide. This weakening of the C=0 bond can be explained by the significant contribution from one of its resonance structures toward the resonance hybrid. Draw that resonance structure for N,N-dimethylacetamide [CH3CON(CH3)2] and explain how it accounts for the weakening of the C=0 bond.

Problem 15.43 calls attention to a resonance structure of an amide that accounts for the lowering of the C=0 stretch frequency. An analogous resonance structure can be drawn for an ester. (a) Draw that resonance structure for methyl acetate (CH3CO,CH3). (b) Based on the fact that an ester's c=0 stretch frequency is higher than an amide's, does that resonance structure have a larger contribution toward the resonance hybrid of an ester or an amide? Using arguments of charge stability, explain why that should be so. In Section 15.5c, we learned that the frequency of the C=0 stretch for an amide is lower than it is for a ketone, suggesting that the C=0 bond is weaker in an amide. This weakening of the C=0 bond can be explained by the significant contribution from one of its resonance structures toward the resonance hybrid. Draw that resonance structure for N,N-dimethylacetamide [CH3CON(CH3)2] and explain how it accounts for the weakening of the C=0 bond.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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