Fundamentals of Organic ChemistryChemistryAmines
Acid amides do not undergo the typical reactions of the carbonyl ( C = O ) group because:
Options
- Ait is amphoteric
- Bit is a weak base
- Cit is a weak acid
- Dits carbonyl carbon is not electron deficient
Correct answer
D. its carbonyl carbon is not electron deficient
Step-by-step solution
In acid amides ( R-CO-NH₂ ), the lone pair of electrons on the nitrogen atom is in conjugation with the electrons of the carbonyl group. This results in resonance: R-C(=O)-NH₂ R-C(-O^-)=N^+H₂ Due to this delocalization of electrons, the electron density on the carbonyl carbon increases significantly. As a result, the carbonyl carbon loses its electrophilic character and is no longer electron deficient. Since typical reactions of the carbonyl group (like nucleophilic addition) require an electron-deficient carbonyl