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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc179

Assertion: Aniline cannot be synthesised by the Gabriel phthalimide method starting from bromobenzene. Reason: The C-Br bond in bromobenzene has partial double bond character, so the phthalimide anion cannot displace the halide by an SN2 pathway.

  1. AAssertion is false but Reason is true
  2. BAssertion is true but Reason is false
  3. CBoth Assertion and Reason are true but the Reason is not the correct explanation of the Assertion
  4. DBoth Assertion and Reason are true and the Reason is the correct explanation of the Assertion

Answer: D

Aryl halides do not undergo nucleophilic substitution with the phthalimide anion because the C-X bond is shortened and strengthened by resonance with the ring (partial double bond character) and the ring blocks backside attack. Hence the Assertion is true and the Reason explains it.
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