medium · MCAT chem-phys
An organic chemist attempts to synthesize an ester via nucleophilic acyl substitution. He finds that reacting a carboxylic acid with an alcohol is slow, but reacting an acid chloride with the same alcohol is much faster.
What is the fundamental electronic reason for this difference?
- Chlorine is actually a larger atom than oxygen, so steric hindrance cannot explain this reactivity difference.
- The chlorine atom is a better leaving group and its electron-withdrawing effect makes the carbonyl carbon more electrophilic.
- Hydroxide is a poor leaving group compared to chloride, since the chloride ion is far more stable after leaving the molecule.
- The nucleophilicity of the alcohol itself is a fixed property that does not meaningfully change between the two reactions compared.
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