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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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Most popular questions from this chapter

Heating compound X with aqueous formaldehyde forms Y \(\left( {{{\bf{C}}_{{\bf{17}}}}{{\bf{H}}_{{\bf{23}}}}{\bf{NO}}} \right)\),which has been converted to a mixture of lupinine and epilupinine, alkaloids isolated from lupin, a perennial ornamental plant commonly seen on the roadside in parts of Alaska (Section 25.10). Identify Y and explain how it is formed.

Question: Rank the following compounds in order of increasing basicity

Synthesize each compound from benzene. Use a diazonium salt as one of the synthetic intermediates.

Explain why m-nitroaniline is a stronger base than p-nitroaniline

Question: Draw the product Y of the following reaction sequence. Y was an intermediate in the remarkable synthesis of cyclooctatetraene by Wilstatter in 1911.
See all solutions

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