Propaneamine by grabriel phthalamid synthesis
Answers
Answer:
Gabriel Phthalimide Synthesis Mechanism has 3 steps. The Synthesis is used to get primary amines from primary alkyl halides and is named after the German scientist Siegmund Gabriel.
The reaction has been generalized for applications in the alkylation of sulfonamides and imides & their deprotection in order to obtain amines. Alkylation of ammonia is quite inefficient, therefore it is substituted with phthalimide anion in the Gabriel synthesis.
Step 1
When potassium hydroxide is introduced to the phthalimide, an acid-base reaction ensues. The hydroxide ion deprotonates the imide. The resulting proton is more acidic than any simple amine (the two adjacent carbonyl-like groups offer resonance stabilization), generating a strong nucleophile – the imide ion.
Step 2
The nucleophilic imide ion attacks the electrophilic carbon of the alkyl halide. The nitrogen atom subsequently replaces the halogen (Fluorine, Chlorine, Bromine or Iodine) in the alkyl halide and bonds with the carbon itself. This results in the formation
Step 3
The mechanism that takes place here is quite similar to base-catalyzed hydrolysis of esters, with nitrogen attached to the R group instead of oxygen. The hydroxide ion attacks the carbon atom bonded to the nitrogen atom, cleaving the N-Alkyl phthalimide. The cation in the base attaches itself to the oxygen atom as well. It is important to note that the nitrogen atom attached to the R group bonds with the hydrogens ejected from the hydroxide ion when the oxygen atom replaces it in the phthalimide.
Explanation:
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