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JEE Advanced levelSingle correct optionDifficulty 3 of 3g3045

Assertion (A): tropylium bromide, , is an ionic, water-soluble salt, unlike an ordinary alkyl bromide. Reason (R): the cycloheptatrienyl cation is planar and cyclic with 6 delocalised pi electrons, so it is aromatic and unusually stable.

  1. AA is true but R is false
  2. BA is false but R is true
  3. CBoth A and R are true and R is the correct explanation of A
  4. DBoth A and R are true but R is not the correct explanation of A

Answer: C

Loss of bromide from cyclohepta-1,3,5-triene-7-yl bromide gives a planar cation with 6 pi electrons over 7 carbons (, ). This aromatic stabilisation makes the cation so stable that the compound exists as an ionic salt, so both statements are true and R explains A.
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