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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– 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

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

Question: Compound X (molecular formula C10H12O) was treated with, NH2NH2, −OHto yield compound Y (molecular formula C10H14). Based on the1HNMR spectra of X and Y were given below, what are the structures of X and Y?

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

Question: Draw a stepwise, detailed mechanism for the dienone–phenol rearrangement, a reaction that forms alkyl-substituted phenols from cyclohexadienones.

In Step [2] of Mechanism 18.1, loss of a proton to form the substitution product was drawn using one resonance structure only. Use curved arrows to show how the other two resonance structures can be converted to the substitution product (PhE) by removal of a proton with: B.
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