Question

Which of the following amines can be synthesized by Gabriel phthalimide reaction?

• A. Neopentylamine
• B. n-butylamine
• C. Triethylamine
• D. t-butylamine

Answer 1

The correct option is B

n-butylamine

Explanation of correct option

(B) n-butylamine

Gabriel Synthesis

• Through nucleophilic substitution with an alkyl halide, the phthalimide produces primary amines.
• In the primary amine, nitrogen will only be connected to one carbon and two hydrogens.
• The amine shouldn't be hindered because Gabriel's Phthalimide Synthesis does not produce hindered amines.

Mechanism of Gabriel Synthesis

• The reaction of potassium hydroxide with the phthalimide also produces a suitable nucleophile in the form of an imide ion.
• In a nucleophilic substitution process, the imide ion converts the alkyl halide into an intermediate called N-alkyl phthalimide.
• A primary alkyl amine results from the hydrolysis or hydrazinolysis of this phthalimide.
• The reaction mechanism is as follows:
• 
• 
• 

Explanation of incorrect options

(A) Neopentylamine

• Neopentylamine the Gabriel phthalimide reaction cannot be used to make it.
• It is a colorless liquid.
• The molecule is the primary amine derivative of neopentane.

(C) Triethylamine

• Triethylamine the Gabriel phthalimide reaction cannot be used to make it.
• It's also known as TEA.

(D) t-butylamine

• t-butylamine the Gabriel phthalimide reaction cannot be used to make it.
• The organic chemical compound tert-Butylamine has the formula ${\left({\mathrm{CH}}_3\right)}_3{\mathrm{CNH}}_2$.
• It's a white liquid with a characteristic amine odor.

Therefore, the correct option is (B) n-butylamine