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Chapter 18: 3P (page 682)

Draw a detailed mechanism for the chlorination of benzene using Cl2andFeCl3 .

Short Answer

Expert verified

The addition of halogen atoms or atoms to benzene yielding an aryl halide is referred to as the halogenation of benzene.

The halogenation reactions are carried out in the presence of Lewis acid catalysts such as AlCl3 or FeBr3.

Step by step solution

01

Halogenation of benzene

The addition of halogen atoms or atoms to benzene yielding an aryl halide is referred to as the halogenation of benzene.

The halogenation reactions are carried out in the presence of Lewis acid catalysts such as AlCl3 or FeBr3.

02

Chlorination of benzene

The reaction of benzene with Cl2in the presence of FeCl3yields chlorobenzene.

Chlorination of benzene

03

Mechanism for the chlorination of benzene

The chlorination of benzene involves three major steps:

[1]. The reaction of Cl2 with FeCl3 yieldsCl+.

[2]. The addition of Cl+to benzene generates a C-Cl bond.

[3]. FeCl4鈥� removes the proton from the carbon bonded to Cl, re-forming the aromatic ring and regenerating the Lewis acid catalyst.

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Most popular questions from this chapter

Synthesize each compound from benzene

Which substituents have an electron-withdrawing and which have an electron-donating inductive effect

aCH3CH2CH2CH2-

bBr-

cCH3CH2O-

Rank the compounds in each group in order of increasing reactivity in electrophilic aromatic substitution: (a) C6H6,C6H5Cl,C6H5CHO; (b) C6H5CH3,C6H5NH2,C6H5CH2NH2.

Question: The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown.

a. Explain why electrophilic substitution occurs on the ring without the N atom for quinoline, but occurs on the ring with the N atom in indole.

b. Explain why electrophilic substitution occurs more readily at C8 than C7 in quinoline.

c. Explain why electrophilic substitution occurs more readily at C3 rather than C2 of indole.

Draw a stepwise mechanism for the following reaction.
See all solutions

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