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Chapter 18: 8P (page 688)

Draw a stepwise mechanism for the following reaction.

Short Answer

Expert verified

The name, electrophilic substitution, comes from the electrophile which is placed on the substrate (electron-rich). Therefore, the carbocations are also substituted as the electrophiles.

Step by step solution

01

Electrophilic substitution reaction

The name, electrophilic substitution, comes from the electrophile which is placed on the substrate (electron-rich). Therefore, the carbocations are also substituted as the electrophiles.

02

Generation of electrophile

Electrophiles are generated in the presence of Lewis acid. The Lewis acid accepts the anion (from the substrate) and completes its octet.

03

Electrophilic substitution and the abstraction of hydrogen

Electrophiles are substituted in the second step on the substrate. The third step involves the abstraction of hydrogen from the base which forms the final product.

04

Explanation

The stepwise mechanism for the given question is shown as:

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Most popular questions from this chapter

Question: Ibufenac, a para-disubstituted arene with the structure HO2CCH2C6H4CH2CH(CH3)2, is a much more potent analgesic than aspirin, but it was never sold commercially because it caused liver toxicity in some clinical trials. Devise a synthesis of ibufenac from benzene and organic halides having fewer than five carbons.

What product is formed when benzene is treated with each organic halide in the presence of AlCl3.

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

Draw the products of each reaction.

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

aCH3CH2CH2CH2-

bBr-

cCH3CH2O-
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