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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

The highly reactive triple bond of benzyne is a powerful dienophile. Predict the product of the Diels鈥揂lder reaction of benzyne (from chlorobenzene and NaOH, heated) with cyclopentadiene.

Phenolphthalein, a common nonprescription laxative, is also an acid-base indicator that is colorless in acid and red in base. Phenolphthalein is synthesized by the acid-catalyzed reaction of phthalic anhydride with 2 equivalents of phenol.

(a) Propose a mechanism for the synthesis of phenolphthalein.

(b) Propose a mechanism for the conversion of phenolphthalein to its red dianion in the base.

(c) Use resonance structures to show that the two phenolic oxygen atoms are equivalent (each with half a negative charge) in the red phenolphthalein dianion.


Phthalic anhydride Phenolphthalein red dianion

Step 2 of the iodination of benzene shows water acting as a base and removing a proton from the sigma complex. We did not consider the possibility of water acting as a nucleophile and attacking the carbocation, as in an electrophilic addition to an alkene. Draw the reaction that would occur if water reacted as a nucleophile and added to the carbocation. Explain why this type of addition is rarely observed.

Predict the site(s) of electrophilic attack on these compounds.

(a)

(b)

Show how you would synthesize the following compounds, using the indicated starting materials.

(a) 3-phenylbutan-1-ol from styrene
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