JEE Main · 2024 · Shift-IIeasyHC-097

The correct arrangement for decreasing order of electrophilic substitution for the following compounds:

Hydrocarbons · Class 11 · JEE Main Previous Year Question

Question

The correct arrangement for decreasing order of electrophilic substitution for the following compounds: image

Options
  1. a

    (IV)>(I)>(II)>(III)(IV) > (I) > (II) > (III)

  2. b

    (III)>(I)>(II)>(IV)(III) > (I) > (II) > (IV)

  3. c

    (II)>(IV)>(III)>(I)(II) > (IV) > (III) > (I)

  4. d

    (II)>(I)>(III)>(IV)(II) > (I) > (III) > (IV)

Correct Answerb

(III)>(I)>(II)>(IV)(III) > (I) > (II) > (IV)

Detailed Solution

Step 1: Identify Groups and Their Effect

From the image, the four compounds are:

  • (I) = Toluene: \ceCH3\ce{-CH3} = activating, ortho/para director
  • (II) = Anisole: \ceOCH3\ce{-OCH3} = strongly activating (lone pair donation), ortho/para director
  • (III) = Chlorobenzene: \ceCl\ce{-Cl} = deactivating (inductive), but ortho/para director
  • (IV) = Benzotrifluoride: \ceCF3\ce{-CF3} = strongly deactivating (no lone pairs, strong inductive withdrawal), meta director

Step 2: Rank Reactivity Toward EAS

Higher electron density in ring = more reactive toward electrophile:

  1. \ceOCH3\ce{-OCH3} (anisole): strongest activator
  2. \ceCH3\ce{-CH3} (toluene): moderate activator
  3. \ceCl\ce{-Cl} (chlorobenzene): deactivating but less than \ceCF3\ce{CF3}
  4. \ceCF3\ce{-CF3} (benzotrifluoride): strongly deactivating

Order: III>I>II>IV\text{III} > \text{I} > \text{II} > \text{IV}

Answer: Option b

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