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Haloalkanes and Haloarenes
Question
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Toluene is nitrated and the resulting product is reduced with tin and hydrochloric acid. The product so obtained is diazotised and then heated with cuprous bromide. The reaction mixture so formed contains

  • mixture of o− and p−bromotoluenes

  • mixture of o− and p−dibromobenzenes

  • mixture of o− and p−bromoanilines

  • mixture of o− and m−bromotoluenes

Answer

A.

mixture of o− and p−bromotoluenes


First, sulphonationis the means to block para position and to reduce the reactivity of phenolic ring against strong oxidising agent HNO3. (The use of conc. HNO3 over phenol cause the oxidation of ring mainly). The strong acidic medium in second step cause desulphonation also.

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