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Home Q & A Board Science-Related Homework Help Chemistry (Moderator: Laser_3)
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divijnanda divijnanda
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6 years ago
Provide a brief explanation to account for the observation that the frequency of the C=O stretching absorption in the infrared spectrum of N,N-dimethylacetamide, CH3CON(CH3)2, is higher than that of methyl acetate, CH3CO2CH3
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6 years ago

The C=O bond of the amide is weaker than that of the ester. Nitrogen is less electronegative than oxygen, and therefore a better electron pair donor. Accordingly, the resonance contributor in which the nitrogen has donated a pair of electrons to the carbonyl carbon atom is an important contributor to the structure.
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