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Chapter 18: Q30P (page 902)

Write the sequence of steps required for the conversion of benzene into benzenediazonium chloride.

Short Answer

Expert verified

The leaving group of a diazonium ion can be replaced by a nucleophile very easily as the nitrogen gas is a leaving group and stable. Some displacements occur using phenyl cations, and others happen using radicals.

Step by step solution

01

Synthesizing substituted benzenes using arene diazonium salts

The leaving group of a diazonium ion can be replaced by a nucleophile very easily as the nitrogen gas is a leaving group and stable. Some displacements occur using phenyl cations, and others happen using radicals.

02

Conversion of benzene to benzene diazonium chloride

Benzene reacts with HNO3 and H2SO4 to form nitrobenzene. This further reacts with hydrogen and palladium catalyst to form aniline. This reacts with sodium nitrite and HCl at 100 degrees Celsius to form benzene diazonium chloride.

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Most popular questions from this chapter

Show how the following compounds can be prepared from benzene:

Question:a. How can aspirin be synthesized from benzene?b. Ibuprofen is the active ingredient in pain relievers such as Advil, Motrin and Nuprin. How can ibuprofen be synthesized from benzene?c. Acetaminophen is the active ingredient in Tylenol. How can acetaminophen be synthesized from benzene?

aspirin ibuprofen acetaminophen

a. Does a coupling reaction have to be used to synthesize p-dipropylbenzene?

b. Can a coupling reaction be used to synthesize p-dipropylbenzene?

Using resonance contributors for the carbocation intermediate, explain why a phenyl group is an ortho–para director.

Explain why hydroxide ion catalyzes the reaction of piperidine with 2,4-dinitroanisole but has no effect on the reaction of piperidine with 1-chloro-2,4-dinitrobenzene.
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