Question
The Gabriel synthesis uses a ____.
Answer
The Gabriel synthesis uses a resonance-stabilized nitrogen nucleophile to synthesize 1° amines via nucleophilic substitution.
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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