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ChemistryMultiple correct+4 / -1Question 32 of 60

JEE Advanced 2013 · Paper 1, Chemistry question 32

Among P, Q, R and S, the aromatic compound(s) is/are

Four reactions: 3-chlorocyclopropene with AlCl₃ gives P; cyclopentadiene with NaH gives Q; hexane-2,5-dione with (NH₄)₂CO₃ at 100-115 °C gives R; cycloheptatrienone (tropone) with HCl gives S.
Choose one or more options
Answer and worked solution

Official answer: A, B, C, D

  • P: AlCl₃ removes Cl⁻ to give the cyclopropenyl cation (2 π electrons). Aromatic.
  • Q: NaH removes a proton to give the cyclopentadienyl anion (6 π electrons). Aromatic.
  • R: Paal-Knorr synthesis: hexane-2,5-dione with ammonia (from (NH₄)₂CO₃) gives 2,5-dimethylpyrrole. Aromatic.
  • S: Tropone is protonated on oxygen to the hydroxytropylium ion (6 π electrons). Aromatic.

(A), (B), (C), (D)

Topics:AromaticityReactive intermediates
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