Question
An amino acid is generated from ____, using two SN2 reactions, hydrolysis, and decarboxylation.
Answer
An amino acid is generated from phthalimide and diethyl bromomalonate, using two SN2 reactions, hydrolysis, and decarboxylation.
Note ↑: The carbonyl carbon of an amide is sp2
hybridized and has trigonal planar geometry. A second
resonance structure can be drawn that delocalizes the nonbonded electron pair on the N atom.
Amides are more resonance stabilized than other acyl compounds, so the resonance structure
having the C=N makes a significant contribution to the hybrid.
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