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JEE Main 2019 · Chemistry · General Organic Chemistry and Isomerism · medium

Benzene is treated in sequence with (i) CH3COCl/anhyd. AlCl3, (ii) Br2/FeBr3, and (iii) Zn-Hg/conc. HCl. The final major product is

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Benzene is treated in sequence with (i) CH3COCl/anhyd. AlCl3\mathrm{CH_3COCl/anhyd.\ AlCl_3}, (ii) Br2/FeBr3\mathrm{Br_2/FeBr_3}, and (iii) Zn-Hg/conc. HCl\mathrm{Zn\text{-}Hg/conc.\ HCl}. The final major product is
  1. A. 1-bromo-4-ethylbenzene
  2. B. 1-bromo-2-ethylbenzene
  3. C. (1-bromoethyl)benzene
  4. D. 1-bromo-3-ethylbenzene
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Answer: (D) 1-bromo-3-ethylbenzene

Friedel-Crafts acylation gives acetophenone. The acetyl group is a meta-directing, deactivating group, so bromination gives 3-bromoacetophenone. Clemmensen reduction (Zn-Hg/HCl\mathrm{Zn\text{-}Hg/HCl}) converts C=O\mathrm{C{=}O} to CH2\mathrm{CH_2}, giving 1-bromo-3-ethylbenzene. Doing the reduction first would make the ethyl group ortho/para-directing and give the 4-bromo isomer; this is why the order of steps matters (acylation, then halogenation).
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