Numford
Name reaction

Fittig reaction

Two molecules of an aryl halide react with sodium in dry ether to give a diaryl (biphenyl).

Class 12, Chapter 6 Haloalkanes and Haloarenes

  1. Br
    BromobenzeneC₆H₅BrHaloarene
  2. Step 1

    Na, dry ether

    Fittig reaction
    i

    Fittig reaction: two aryl halides couple with sodium.

    BiphenylC₆H₅C₆H₅Arene

Reagents: Na, dry ether

Mechanism

How it works

  1. Sodium converts the aryl halide to an aryl sodium.
  2. The aryl sodium couples with a second aryl halide.
  3. NaX is lost and a biaryl forms.
Used to prepare

What it makes

Biphenyl and other diaryls.

Limitations

Where it fails

Only aryl halides are used. With one aryl and one alkyl halide the reaction is called Wurtz-Fittig.

Which chapter

Class 12, Chapter 6 Haloalkanes and Haloarenes

Questions

Fittig reaction: quick answers

What is the product of the Fittig reaction on chlorobenzene?

Biphenyl.

How is Fittig different from Wurtz-Fittig?

Fittig uses only aryl halides; Wurtz-Fittig uses an aryl halide with an alkyl halide.

Which solvent is used?

Dry ether.

Plan an organic conversion