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In: Chemistry

Using benzene or toluene as the only aromatic organic starting material, devise a synthesis for each...

Using benzene or toluene as the only aromatic organic starting material, devise a synthesis for each of the following:

a. o-chlorotoluene

b. 3-bromonitrobenzene

c. p-toluenesulfonic acid

d. 2-chloronitrobenzene

Expert Solution

Answer.a) Synthesis of o-chlorotoluene taking benzene as starting material.

Friedal craft's alkylation of benzene,

C₆ H₆ + CH₃ Cl C₆ H₅ CH₃ +HCl

Chlorination of toluene:

C₆ H₅ CH₃ + Cl₂ o-chlorotoluene +p-chlorotoluene

b) Synthesis of 3-bromonitrobenzene using benzene

Nitration of benzene

C₆ H₆ +HNO3 C₆ H₅ NO₂ +H2O

Bromination of nitrobenzene

C₆ H₅ NO₂ + Br2 3-bromonitrobenzene + HBr

c) p-toluenesulfonic acid

Sulfonation of toluene

C₆ H₅ CH₃ + Conc.H2SO4 p-toluenesulfonic acid + o-toluenesulfonic acid

d) 2-Chloronitrobenzene

Chlorination of benzene:

C₆ H₆ + Cl2 C₆ H₅ Cl + HCl

Nitration of chlorobenzene

C₆ H₅ Cl + HNO3 2-chloronitrobenzene + 4-chloronitrbenzene

queen_honey_blossom answered 3 years ago

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