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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc198

Assertion: Aniline does not undergo Friedel-Crafts alkylation with and anhydrous . Reason: The nitrogen lone pair of aniline forms a salt-like complex with , and the resulting positively charged nitrogen strongly deactivates the ring.

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

Answer: B

Aniline is a Lewis base and the Lewis acid AlCl3 binds to its nitrogen, so the group on the ring becomes a positively charged, strongly electron-withdrawing substituent. This deactivation prevents electrophilic alkylation. Assertion and Reason are true, and the Reason explains the Assertion.
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