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Unformatted text preview: CO2Et Purpose of the problem Drawing mechanisms for two types of nucleophilic substitution in the same sequence to make a β- lactam antibiotic. Suggested solution We need an SN2 reaction at a primary carbon and a nucleophilic substitution at the carbonyl group with the amino group as the nucleophile in both cases. The carbonyl group reaction probably happens first. Don’t worry if you didn’t deprotonate the amide before the SN2 reaction. The stereochemistry is the...
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This document was uploaded on 02/10/2014.

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