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Organic conversion

Benzene to m-nitroacetophenone

2 steps: Friedel-Crafts acylation, then substitution

Class 12, Chapter 8 Aldehydes, Ketones and Carboxylic Acids

  1. BenzeneC₆H₆Arene
  2. Step 1

    CH₃COCl, anhydrous AlCl₃

    Friedel-Crafts acylation
    i

    Friedel-Crafts acylation: the acyl group deactivates the ring, so it stops at one substitution.

    O
    AcetophenoneC₆H₅COCH₃Ketone
  3. Step 2

    conc. HNO₃ + conc. H₂SO₄

    i

    The acetyl group is meta directing, so nitrate after acylation to get the meta isomer.

    ON+OO−
    m-Nitroacetophenonem-O₂NC₆H₄COCH₃Ketone

Exam answer

  1. Step 1: Benzene to acetophenone: CH₃COCl, anhydrous AlCl₃.
  2. Step 2: Acetophenone to m-nitroacetophenone: conc. HNO₃ + conc. H₂SO₄.
Why these reagents

Reagent and reason, step by step

  • Step 1: Benzene to acetophenone: CH₃COCl, anhydrous AlCl₃ Friedel-Crafts acylation: the acyl group deactivates the ring, so it stops at one substitution.
  • Step 2: Acetophenone to m-nitroacetophenone: conc. HNO₃ + conc. H₂SO₄ The acetyl group is meta directing, so nitrate after acylation to get the meta isomer.
Questions

Benzene to m-nitroacetophenone: quick answers

How many steps does it take to convert benzene to m-nitroacetophenone?

2 steps: Benzene, then acetophenone, then m-nitroacetophenone.

Which named reaction is used to convert benzene to m-nitroacetophenone?

Friedel-Crafts acylation. Benzene reacts with an acyl chloride or anhydride in the presence of anhydrous AlCl3 to give an aromatic ketone.

What is the reagent for step 1 of benzene to m-nitroacetophenone?

Benzene to acetophenone: CH₃COCl, anhydrous AlCl₃. Friedel-Crafts acylation: the acyl group deactivates the ring, so it stops at one substitution.

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