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When chlorobenzene is treated with acetyl chloride in the presence of anhydrous AlCl3 , 4-Chloroacetophenone is formed as the major product. It is an example of

  • A.Nucleophilic substitution
  • B.Electrophilic substitution
  • C.Free radical substitution
  • D.Nucleophilic addition
  • E.Electrophilic addition

Answer: B

The reaction is an example of Electrophilic substitution.

This is Friedel-Crafts acylation. Anhydrous AlCl3, a Lewis acid, takes chloride from acetyl chloride and generates the acylium ion, CH3CO+, a strong electrophile. The electrophile attacks the aromatic ring and a ring hydrogen is lost, so an acetyl group replaces hydrogen on the ring. Chlorine is an ortho, para director, and the bulky acyl group goes mainly to the less crowded para position, which is why 4-chloroacetophenone is the major product.

The ring is not attacked by a nucleophile or a free radical, and nothing is added across a double bond: the aromatic ring survives intact, so neither kind of addition applies.

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