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Chapter 25: PROBLEM 25.31 (page 1033)

Question: Devise a synthesis of each compound from benzene.

a.

b.

c.

d.

Short Answer

Expert verified

Answer

a.

b.

c.

d.

Step by step solution

01

Substitution product of aryl diazonium salts

Aryl diazonium salts undergo substitution of N2O by an atom or group of atoms to form substituted benzene derivatives.

02

Synthesis of the compound from benzene

Benzene undergoes nitration-reduction to form aniline which reacts with nitrous acid forming a diazonium salt.

a. Diazonium salt reacts with fluoroboric acid (HBF4) to form an aryl fluoride.

Synthesis of aryl fluoride

b. Diazonium salt reacts with H2O to form a benzene-1,3-diol (resorcinol).

Synthesis of benzene-1,3-diol

c. O-toluidine forms diazonium salt when it reacts with KI to give 2-iodotoluene.

Synthesis of 2-iodotoluene

d. The diazonium salt reacts with phosphoric acid (H3PO4) to give 1,3,5-trichloro benzene.

Synthesis of 1,3,5-trichloro benzene

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