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.

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Attachments

Number 5 in 71 will occour even though both ester and amide is less reactive then aldehyd and ketones.pdf
Number 5 in 71 will occour even though both ester and amide is less reactive then aldehyd and ketones.docx

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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