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Explaining reactivity of amines with carboxylic acids versus esters

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The question is why there is a distinction between OH and OR as leaving groups. The document also has a question about why a sp3 intermediate is unstable. It is attached in the files below.

© BrainMass Inc. brainmass.com September 21, 2018, 12:03 am ad1c9bdddf - https://brainmass.com/chemistry/organic-reaction-intermediates-and-mechanisms/explaining-reactivity-of-amines-with-carboxylic-acids-versus-esters-582473

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Solution Summary

A brief explanation is given to explain why carboxylic acids don't undergo nucleophilic addition with amines but esters do.

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