JEE Main · 2021 · Shift-IIhardHC-108

The correct sequence of reagents used in the preparation of 4-bromo-2-nitroethyl benzene from benzene is:

Hydrocarbons · Class 11 · JEE Main Previous Year Question

Question

The correct sequence of reagents used in the preparation of 4-bromo-2-nitroethyl benzene from benzene is:

Options
  1. a

    \ceHNO3/H2SO4\ce{HNO3/H2SO4}, \ceBr2/AlCl3\ce{Br2/AlCl3}, \ceCH3COCl/AlCl3\ce{CH3COCl/AlCl3}, \ceZnHg/HCl\ce{Zn-Hg/HCl}

  2. b

    \ceCH3COCl/AlCl3\ce{CH3COCl/AlCl3}, \ceBr2/AlBr3\ce{Br2/AlBr3}, \ceHNO3/H2SO4\ce{HNO3/H2SO4}, \ceZn/HCl\ce{Zn/HCl}

  3. c

    \ceBr2/AlBr3\ce{Br2/AlBr3}, \ceCH3COCl/AlCl3\ce{CH3COCl/AlCl3}, \ceHNO3/H2SO4\ce{HNO3/H2SO4}, \ceZn/HCl\ce{Zn/HCl}

  4. d

    \ceCH3COCl/AlCl3\ce{CH3COCl/AlCl3}, \ceZnHg/HCl\ce{Zn-Hg/HCl}, \ceBr2/AlBr3\ce{Br2/AlBr3}, \ceHNO3/H2SO4\ce{HNO3/H2SO4}

Correct Answerd

\ceCH3COCl/AlCl3\ce{CH3COCl/AlCl3}, \ceZnHg/HCl\ce{Zn-Hg/HCl}, \ceBr2/AlBr3\ce{Br2/AlBr3}, \ceHNO3/H2SO4\ce{HNO3/H2SO4}

Detailed Solution

image Key Points:

  • Use acylation then reduction (not direct alkylation) to get ethyl group cleanly
  • Clemmensen: Zn-Hg/HCl reduces C=O to CH2
  • Order of substitution determines regioselectivity of final product

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