Which of the following amines cannot be prepared by Gabriel Phthalimide synthesis?

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${(C H_{3})}_{3} N$

$C_{6} H_{5} N H_{2}$

$H_{2} C = C H - N H_{2}$

${(C H_{3})}_{2} N H$

answer is A, B, C, D.

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Detailed Solution

Gabriel's synthesis cannot prepare aniline. Using this process, aniline can not be prepared, because aryl halides do not undergo nucleophilic substitution with the phthalimide-formed anion.

As a result of resonance, the carbon-halogen bond acquires some double bond character. Hence, vinyl halide does not undergo nucleophilic substitution reaction to participate in Gabriel Phthalimide synthesis to form vinyl amine.

Option C and Option D are secondary and tertiary amines respectively, which cannot be prepared by Gabriel Phthalimide synthesis.

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