Question

Which of the following Amine will be prepared by the Gabriel phthalimide reaction?

• A. n-Butylamine
• B. Triethylamine
• C. neo-Pentylamine
• D. tert-Butylamine

Answer 1

The correct option is A

n-Butylamine

The explanation of the correct answer

(A) n-Butylamine

1. Gabriel phthalimide synthesis -When phthalimide is treated with alcoholic $\mathrm{KOH}$ and forms Potassium salt of Phthalimide and when it is heated with alkyl halide it forms N-Alkyl phthalimide.
2. Then hydrolysis of N-Alkyl phthalimide forms corresponding primary amine and Phthalic acid.
3. n-Butylamine is a primary amine and hence can be prepared by Gabriel phthalimide synthesis.

The explanation for the incorrect answer.

(B)Triethylamine

1. Triethylamine is not a primary amine it is a tertiary amine so cannot be synthesized by the Gabriel phthalimide reaction.

(C) neo-Pentylamine

1. neo-Pentylamine is a primary amine but it is highly sterically hindered due to which it decreases the rate of reaction.
2. So it cannot be prepared by Gabriel Phthalimide synthesis.

(D)tert-Butylamine

1. tert-Butylamine isa primary amine and sterically hindered due to which it can decrease the rate of reaction.
2. So that it cannot be synthesized by Gabriel phthalimide reaction.

Thus, n-Butylamine will be prepared by the Gabriel phthalimide reaction.