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Chapter 17: Q2P (page 849)

Propose a mechanism for the aluminum chloride-catalyzed reaction of benzene with chlorine.

Short Answer

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The mechanism for the aluminum chloride-catalyzed reaction of benzene with chlorine is as follows:

Step by step solution

01

Chlorination of benzene

The chlorination of benzene works much like bromination except whenAlCl3 is used as a Lewis acid catalyst.It is an electrophilic aromatic substitution.

02

Mechanism of the aluminum chloride-catalyzed reaction

In the first step, theCl2 attacks theAlCl3 .

Cl2attacks theAlCl3

In the second step, the benzene attacks the product formed in the first step.AlCl4_and chlorobenzene carbocation is formed, in which the positive charge delocalizes at the 1st, 3rd, and 5th positions. The chloride ionAlCl4_ of makes a bond with the H of benzene and forms HCl. The other product formed is chlorobenzene.

Mechanism of the aluminum chloride-catalyzed reaction

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Most popular questions from this chapter

To synthesize m-ethylbenzenesulfonic acid, a student attempted the Friedel–Crafts alkylation of benzenesulfonic acid with bromoethane. Do you predict that this reaction was successful? If not, propose an alternative synthesis.

m-ethylbenzenesulfonic acid

When 1,2-dibromo-3,5-dinitrobenzene is treated with excess NaOH at 50 °C, only one of the bromine atoms is replaced. Draw an equation for this reaction, showing the product you expect. Give a mechanism to account for the formation of your proposed product.

A graduate student tried to make o-fluorophenylmagnesium bromide by adding magnesium to an ether solution of o-fluorobromobenzene. After obtaining puzzling results with this reaction, she repeated the reaction by using as solvent some tetrahydrofuran that contained a small amount of furan. From this reaction, she isolated a fair yield of the compound that follows. Propose a mechanism for its formation

Phenol reacts with three equivalents of bromine in CCl4(in the dark) to give a product of formula C6H3OBr3. When this product is added to bromine water, a yellow solid of molecular formula C6H2OBr4 precipitates out of the solution. The IR spectrum of the yellow precipitate shows a strong absorption (much like that of a quinone) around 1680cm-1 . Propose structures for the two products.

The antioxidants BHA and BHT are commonly used as food preservatives. Show how BHA and BHT can be made from phenol and hydroquinone.
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