gabriel synthesis

Question

Gabriel phthalimide synthesis is used to prepare:

RankGuru · Accepted Answer

1. **Steps**: 
   - Phthalimide + $KOH 	o$ Potassium Phthalimide.
   - Potassium Phthalimide + $R-X 	o$ N-Alkylphthalimide.
   - N-Alkylphthalimide + Hydrazine (or boiling $NaOH$) $	o$ **Primary Amine** ($R-NH_2$).
2. **Selectivity**: Pure primary amines are obtained because the Nitrogen is 'locked' in the ring, preventing over-alkylation to secondary or tertiary amines.
3. **Limitation**: It cannot be used to prepare aromatic amines (like aniline) because aryl halides ($C_6H_5X$) do not undergo nucleophilic substitution with potassium phthalimide under ordinary conditions.

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gabriel synthesis

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