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← JEE Advanced 2017 · Paper 2
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JEE Advanced 2017 · Paper 2, Chemistry question 18

Passage

PARAGRAPH 2

The reaction of compound P with CHX3MgBr\ce{CH3MgBr} (excess) in (CX2HX5)X2O\ce{(C2H5)2O} followed by addition of HX2O\ce{H2O} gives Q. The compound Q on treatment with HX2SOX4\ce{H2SO4} at 0°C gives R. The reaction of R with CHX3COCl\ce{CH3COCl} in the presence of anhydrous AlClX3\ce{AlCl3} in CHX2ClX2\ce{CH2Cl2} followed by treatment with HX2O\ce{H2O} produces compound S. [Et in compound P is ethyl group]

P → Q → R → S

P: ethyl 3-(4-tert-butylphenyl)propanoate, (H₃C)₃C-C₆H₄-CH₂CH₂CO₂Et (para), converted in turn to Q, R and S.

The reactions, Q to R and R to S, are

Choose one option
Answer and worked solution

Official answer: D

  • Q → R: the acid generates a carbocation that alkylates its own ring. That is an intramolecular Friedel-Crafts alkylation (the loss of water is how the cation forms, not a separate product-forming step).
  • R → S: Friedel-Crafts acylation.

(D)