Numford
Name reaction

Wurtz-Fittig reaction

A mixture of an aryl halide and an alkyl halide reacts with sodium in dry ether to give an alkylbenzene.

Class 12, Chapter 6 Haloalkanes and Haloarenes

  1. Br
    BromobenzeneC₆H₅BrHaloarene
  2. Step 1

    CH₃Br, Na, dry ether

    Wurtz-Fittig reaction
    i

    Wurtz-Fittig reaction: an aryl halide and an alkyl halide couple with sodium.

    TolueneC₆H₅CH₃Arene

Reagents: Aryl halide + alkyl halide, Na, dry ether

Mechanism

How it works

  1. Sodium converts both halides to reactive organosodium species.
  2. The alkyl group joins the aryl group.
  3. NaX is lost.
Used to prepare

What it makes

Alkylbenzenes such as toluene.

Limitations

Where it fails

Some biphenyl and some dialkane form as side products.

Which chapter

Class 12, Chapter 6 Haloalkanes and Haloarenes

Questions

Wurtz-Fittig reaction: quick answers

What is the difference between Wurtz and Wurtz-Fittig?

Wurtz couples two alkyl halides; Wurtz-Fittig couples an alkyl halide with an aryl halide.

What is the Fittig reaction?

Two molecules of aryl halide react with sodium in dry ether to give a biaryl such as biphenyl.

Why is dry ether used?

Sodium reacts with water.

Plan an organic conversion