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Chapter 18: 6P (page 684)

What acid chloride would be needed to prepare each of the following ketones from benzene using a Friedel–Crafts acylation?

Short Answer

Expert verified

The reactions involving the replacement of a hydrogen atom of the benzene ring with an acyl group are termed as Friedel-Crafts acylation reactions.

In the Friedel-Crafts acylation reaction, the benzene is made to react with an acyl chloride RCOClin presence of a Lewis acid catalyst.

Step by step solution

01

Friedel–Crafts acylation reaction

The reactions involving the replacement of a hydrogen atom of the benzene ring with an acyl group are termed as Friedel-Crafts acylation reactions.

In the Friedel-Crafts acylation reaction, the benzene is made to react with an acyl chloride RCOClin presence of a Lewis acid catalyst.

02

Reaction of benzene with an acyl chloride

The reaction of benzene with an acid chloride is shown below.

03

The acyl chlorides required to prepare the given ketones

Replacing the benzene ring in the given ketones with the chlorine atom gives the corresponding acyl chlorides used in the synthesis of the given ketones.

a

b

c

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Most popular questions from this chapter

Question: Using resonance structures, explain why a nitroso group (-NO) is an ortho, para director that deactivates a benzene ring toward electrophilic attack.

Draw the product of each reaction.

Draw all resonance structures for the carbocation formed by ortho attack of the electrophile NO2+ on each starting material. Label any resonance structures that are especially stable or unstable.

Question: Ibufenac, a para-disubstituted arene with the structure HO2CCH2C6H4CH2CH(CH3)2, is a much more potent analgesic than aspirin, but it was never sold commercially because it caused liver toxicity in some clinical trials. Devise a synthesis of ibufenac from benzene and organic halides having fewer than five carbons.

What products are formed when benzene is treated with each alkyl chloride and AlCl3?
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