Solution Found!
What alkyl bromide would you use in a Gabriel synthesis to
Chapter 16, Problem 44P(choose chapter or problem)
What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?
a. Pentylamine b. Isohexylamine
c. benzylamine d. cyclohexylamine
Questions & Answers
QUESTION:
What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?
a. Pentylamine b. Isohexylamine
c. benzylamine d. cyclohexylamine
ANSWER:Solution 44P
The Gabriel synthesis converts an alkyl halide into a primary amine via nucleophilic substitution followed by the hydrolysis.
(a)Treatment of pentyl bromide with phthalimide in the presence of strong base gives an N-substituted imide followed by the hydrolysis gives a primary amine and a dicarboxylate byproduct. Thus, the reaction is as follows:
