Destroyer orgo 38

[gegogi]

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Why the propanamide is very unreactive in nucleophilic acyl substituion? I think the amide is one of the carboxylic derivatives(alcyl halide, ester, anhydride) and is very reactive in nucleophilic acyl substitution, i guess. No?"

 

[nze82]

Why the propanamide is very unreactive in nucleophilic acyl substituion? I think the amide is one of the carboxylic derivatives(alcyl halide, ester, anhydride) and is very reactive in nucleophilic acyl substitution, i guess. No?"

The lone pair of electrons on N ruins the partial positive charge on the carbonyl carbon due to their inductive effect, making the attack of the nucleophile less efficient.

 

[gegogi]

Thank you so much!

 

[loveoforganic]

The lone pair of electrons on N ruins the partial positive charge on the carbonyl carbon due to their inductive effect, making the attack of the nucleophile less efficient.

Resonance effect.