Write down mechanism Gabriel's phthalimide synthesis for the preparati...
Introduction:
Gabriel's phthalimide synthesis is a method used to prepare primary amines by the reaction of phthalimide with a strong base, followed by hydrolysis. This reaction is commonly used to synthesize aliphatic and aromatic primary amines, including ethylamine (EtNH2).
Gabriel's Phthalimide Synthesis:
The synthesis of ethylamine (EtNH2) using Gabriel's phthalimide synthesis involves the following steps:
1. Preparation of Phthalimide:
- Phthalimide is prepared by the reaction of phthalic anhydride with aqueous ammonia.
- In a round-bottom flask, phthalic anhydride is dissolved in a suitable solvent (such as ethanol or dimethylformamide).
- Aqueous ammonia is slowly added to the flask while stirring.
- The reaction mixture is heated and refluxed for a specific period of time.
- The resulting solution is cooled, and the precipitated phthalimide is collected by filtration, washed, and dried.
2. Reaction with Ethyl Bromide:
- The phthalimide obtained in the previous step is reacted with ethyl bromide to form the corresponding N-ethyl phthalimide.
- In a round-bottom flask, the phthalimide is dissolved in a suitable solvent (such as ethanol or dimethylformamide).
- Ethyl bromide is slowly added to the flask while stirring.
- The reaction mixture is heated and refluxed for a specific period of time.
- The resulting solution is cooled, and the precipitated N-ethyl phthalimide is collected by filtration, washed, and dried.
3. Deprotection of N-Ethyl Phthalimide:
- The N-ethyl phthalimide obtained in the previous step is deprotected to obtain the primary amine, ethylamine.
- The N-ethyl phthalimide is reacted with a strong base, such as potassium hydroxide (KOH) or sodium hydroxide (NaOH).
- The reaction mixture is heated and refluxed for a specific period of time.
- The resulting solution is cooled, and the phthalic acid salt is precipitated.
- The phthalic acid salt is then acidified to obtain the primary amine, ethylamine.
Conclusion:
Gabriel's phthalimide synthesis is a versatile method for the preparation of primary amines. By following the steps mentioned above, ethylamine (EtNH2) can be synthesized from phthalimide. It is important to use appropriate solvents, reactants, and reaction conditions to ensure a successful synthesis.