Question

Which of the following amines can not be prepared by Gabriel phthalimide synthesis?

• A. Ethylamine
• B. Sec-butylamine
• C. Aniline
• D. Isopropylamine

Hint:

Remember, Gabriel phthalimide synthesis is best for preparing aliphatic primary amines, not aromatic amines like aniline.

Answer 1

The Correct Option is C

Step 1: Understanding Gabriel phthalimide synthesis.
Gabriel phthalimide synthesis is a method used to prepare primary amines. It involves the reaction of phthalimide with an alkyl halide to form a phthalimide salt, which upon hydrolysis gives the corresponding amine.
Step 2: Analyzing the options.
(A) Ethylamine: Ethylamine can be synthesized using Gabriel phthalimide synthesis, as it involves an alkyl halide (ethyl bromide) and phthalimide.
(B) Sec-butylamine: Sec-butylamine can also be synthesized in a similar manner using sec-butyl bromide.
(C) Aniline: Aniline cannot be synthesized using Gabriel phthalimide synthesis, as it is a primary amine with an aromatic group. The synthesis works only for aliphatic amines.
(D) Isopropylamine: Isopropylamine can be synthesized using Gabriel phthalimide synthesis, using isopropyl bromide as the alkyl halide.
Step 3: Conclusion.
The correct answer is (C) Aniline, as it cannot be prepared by Gabriel phthalimide synthesis due to its aromatic nature.