The carbonyl stretch of acetyl chloride (CH3COCI) is found at 1806 cm-1. Is the C=0 bond stronger or weaker than the one in an amide? What does this suggest about the resonance contribution of a lone pair on Cl in an acid chloride compared 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 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.

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The carbonyl stretch of acetyl chloride (CH3COCI) is found at 1806 cm-1. Is the C=0 bond stronger or weaker than
the one in an amide? What does this suggest about the resonance contribution of a lone pair on Cl in an acid chloride
compared to that of the lone pair on N in an amide? Explain. Hint: See Problems 15.43 and 15.44.
Transcribed Image Text:The carbonyl stretch of acetyl chloride (CH3COCI) is found at 1806 cm-1. Is the C=0 bond stronger or weaker than the one in an amide? What does this suggest about the resonance contribution of a lone pair on Cl in an acid chloride compared 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 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.
Transcribed Image Text: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.
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