Question

Why is an amide less reactive to nucleophilic acyl substitution than an acid chloride?

Answer 1

An amide is less reactive to nucleophilic acyl substitution than an acid chloride because more electron density is donated to the carbonyl by nitrogen.

What is electron density?

In quantum chemistry, electron density, also known as electronic density, is a metric for the likelihood that an electron will be found at a microscopic portion of space surrounding a specific point. The likelihood of finding an electron at a particular position near an atom or molecule is represented by electron density. In general, areas with a high electron density are where the electron is most likely to be located. The attractive forces between the electrons and the nuclei in a molecule are what hold the nuclei together in molecule, hence the electron density is essential to the bonding and geometry of a molecule. The repulsions between the nuclei and the electrons function as an antagonist to these attractive forces.

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