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Organic conversion

Benzene to chlorobenzene

1 step: substitution

Class 12, Chapter 6 Haloalkanes and Haloarenes

  1. BenzeneC₆H₆Arene
  2. Step 1

    Cl₂, anhydrous FeCl₃

    i

    Electrophilic substitution; the Lewis acid polarises Cl₂.

    Cl
    ChlorobenzeneC₆H₅ClHaloarene

Exam answer

  1. Step 1: Benzene to chlorobenzene: Cl₂, anhydrous FeCl₃.
Alternative routes (1)
  • Benzene → Nitrobenzene → Aniline → Benzene diazonium chloride → Chlorobenzene
    1. Benzene to nitrobenzene: conc. HNO₃ + conc. H₂SO₄, 323 to 333 K.
    2. Nitrobenzene to aniline: Sn + conc. HCl.
    3. Aniline to benzene diazonium chloride: NaNO₂ + HCl, 273 to 278 K.
    4. Benzene diazonium chloride to chlorobenzene: Cu₂Cl₂, HCl.
Why these reagents

Reagent and reason, step by step

  • Step 1: Benzene to chlorobenzene: Cl₂, anhydrous FeCl₃ Electrophilic substitution; the Lewis acid polarises Cl₂.
Questions

Benzene to chlorobenzene: quick answers

How many steps does it take to convert benzene to chlorobenzene?

1 step: Benzene, then chlorobenzene.

Which named reaction is used to convert benzene to chlorobenzene?

None of the steps has a name. They are substitution, so write the reagent and the condition for each step.

What is the reagent for step 1 of benzene to chlorobenzene?

Benzene to chlorobenzene: Cl₂, anhydrous FeCl₃. Electrophilic substitution; the Lewis acid polarises Cl₂.

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