NEETChemistryAmines
Given below are two statements: one is labelled as Assertion (A) and the other is labelled as Reason (R). Assertion (A): Aniline cannot be prepared by Gabriel phthalimide synthesis. Reason (R): Aryl halides do not undergo nucleophilic substitution with the anion formed by phthalimide under ordinary conditions. In the light of the above statements, choose the most appropriate answer from the options given below:
Options
- ABoth (A) and (R) are correct but (R) is not the correct explanation of (A)
- B(A) is correct but (R) is not correct
- CBoth (A) and (R) are correct and (R) is the correct explanation of (A)
- D(A) is not correct but (R) is correct
Correct answer
C. Both (A) and (R) are correct and (R) is the correct explanation of (A)
Step-by-step solution
Gabriel phthalimide synthesis is used for the preparation of aliphatic primary amines. Aniline (an aromatic primary amine) cannot be prepared by this method because the synthesis requires the nucleophilic substitution of a halide by the phthalimide anion. Aryl halides do not undergo nucleophilic substitution reactions easily under ordinary conditions due to the partial double bond character of the C - X bond. Thus, the phthalimide anion cannot attack the aryl halide to form N -phenylphthalimide. Therefore, both Ass