| Feature | Gabriel Phthalimide | Hofmann Bromamide |
|---|---|---|
| Starting material | Alkyl halide (RX) | Amide (RCONH2) |
| Product | RNH2 (1° only) | RNH2 (1° only, one less C) |
| Mechanism | SN2 on RX | 1,2-Rearrangement |
| Carbon count | Same as RX | One fewer than amide |
| Makes ArNH2? | No (ArX no SN2) | Yes (from ArCONH2) |
| Makes 2°/3°? | No | No |
| Side products | Minimal | Na2CO3, NaBr |
| Both give pure 1° amines. Gabriel is better for aliphatic amines when the halide is available. Hofmann is the method of choice when descending the homologous series or starting from amides. JEE frequently asks which method can/cannot prepare a specific amine. |
Part of JOC-06 — Amines & Diazonium Salts
Hofmann vs Gabriel — Comparison
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