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
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Chapter1: Chemical Foundations
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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.
Transcribed Image Text: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.
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