Aliphatic Compounds Containing Nitrogen - Result Question 5

5. Which of the following amines can be prepared by Gabriel phthalimide reaction?

(2019 Main, 8 April I)

(a) $n$ - butylamine

(b) triethylamine

(c) $t$-butylamine

(d) neo -pentylamine

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Answer:

Correct Answer: 5. (a)

Solution:

$n$-butylamine $\left(CH _3 CH _2 CH _2 CH _2 NH _2\right)$ can be prepared by Gabriel phthalimide reaction. This method produces only primary amines without the traces of secondary or tertiary amines. In this method, phthalimide is treated with ethanolic $KOH$, it forms potassium salt of phthalimide which on heating with alkyl halide followed by alkaline hydrolysis forms corresponding primary amines.

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Triethylamine, $t$-butylamine and neo-pentylamine cannot be prepared by Gabriel phthalimide reaction.