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Chapter 16: Q6 P (page 493)

What is the major monosubstitution product from the Friedel–Crafts reaction of benzene with 1-chloro-2-methylpropane in the presence of AlCl3 ?

Short Answer

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Alkylation reactions constitute a useful electrophilic aromatic substitution reaction. The reaction involves the introduction of an alkyl group into the benzene ring. The reagents used for this reaction are an alkyl chloride in the presence of .

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01

Friedel-Crafts reaction

Alkylation reactions constitute a useful electrophilic aromatic substitution reaction. The reaction involves the introduction of an alkyl group into the benzene ring. The reagents used for this reaction are an alkyl chloride in the presence of .

02

Major monosubstitution product from the Friedelcraft’s reaction of benzene with 1-chloro-2-methylpropane

The electrophile involved when 1-chloro-2-methylpropane is used in Friedal-Crafts reaction is 1-chloro-2-methylpropyl carbocation. It is primary and will rearrange to form a more stable tert-butyl carbocation. This carbocation attacks the benzene ring to form tert-butyl benzene as the product. The reaction can be given as:

Friedelcraft’s reaction of benzene with 1-chloro-2-methylpropane

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Most popular questions from this chapter

Triphenylmethane can be prepared by reaction of benzene and chloroform in the presence of AlCl3. Propose a mechanism for the reaction.

As written, the following syntheses have flaws. What is wrong with

each?

Refer to Table 6-3 on page 170 for a quantitative idea of the stability of a benzyl radical. How much more stable (in kJ/mol) is the benzyl radical than a primary alkyl radical? How does a benzyl radical compare in stability to an allylradical?

Question: Phenols (ArOH) are relatively acidic, and the presence of a substituent group on the aromatic ring has a large effect. Thepka of unsubstituted phenol, for example, is 9.89, while that of p-nitrophenol is 7.15. Draw resonance structures of the corresponding phenoxide anions and explain the data.

Question: How would you synthesize the following compounds from benzene? Assume that ortho and para isomers can be separated.

a)

b)
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