Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Haloalkanes and Haloarenes

Question:

The above reaction is an example of

Options:

Sandmeyer's reaction

Wurtz reaction

Wurtz Fittig reaction

Kolbe reaction

Correct Answer:

Wurtz Fittig reaction

Explanation:

The correct answer is Option (3) → Wurtz Fittig reaction

The reaction of chlorobenzene and methyl chloride with sodium in dry ether is an example of the Wurtz-Fittig reaction.

Reaction Details

In this process, an aryl halide (chlorobenzene) and an alkyl halide (methyl chloride) are treated with sodium metal in the presence of dry ether to yield an alkyl-substituted aromatic compound (toluene).

$C_6H_5Cl + CH_3Cl + 2Na \overset{\text{dry ether}}{\longrightarrow} C_6H_5CH_3 (\text{Toluene}) + 2NaCl$

Comparison of Related Reactions

It is easy to confuse these similar coupling reactions, but they differ based on the starting materials used:

Reaction Name

Reactants

Typical Product

Wurtz Reaction

Two alkyl halides

Higher alkanes

Fittig Reaction

Two aryl halides

Biaryl compounds (e.g., biphenyl)

Wurtz-Fittig Reaction

One alkyl and one aryl halide

Alkyl-substituted arenes (e.g., toluene)

Key Points

  • Reagent: Sodium metal acts as a reducing agent, facilitating the coupling of carbon atoms.
  • Solvent: Dry ether is essential because it is an aprotic non-polar solvent that prevents the highly reactive sodium from reacting with water.
  • Mechanism: The reaction can proceed via either a radical mechanism (formation of alkyl/aryl radicals) or an organo-alkali mechanism (formation of an intermediate organosodium compound).

The correct answer is: Wurtz Fittig reaction