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Chapter 18: Q 59. (page 724)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

Expert verified

The mechanism for the given reaction is following:

Step by step solution

01

Nucleophilic aromatic substitution reaction

The aromatic nucleophilic substitution reaction takes place by the elimination-addition mechanism. In this mechanism, the substitution can take place on the carbon attached to the leaving group as well as the adjacent carbon atom.

This results in the formation of two possible products because of the formation of the benzyne intermediate.

02

The stepwise mechanism for the given reaction

The given reaction proceeds by the abstraction of a proton by the base in the first step and results in the formation of the benzyne intermediate as shown below:

In the next step, the intramolecular ring closure takes place and results in the formation of the following product:

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Most popular questions from this chapter

Question: Although two products (A and B) are possible when naphthalene undergoes electrophilic aromatic substitution, only A is formed. Draw resonance structures for the intermediate carbocation to explain why this is observed.

Question: Friedel-Crafts alkylation of benzene with (R)-2-chlorobutane and AlCl3 affords sec-butylbenzene.

  1. How many stereogenic centers are present in the product?
  2. Would you expect the product to exhibit optical activity? Explain, with reference to the mechanism.

Question: Draw a stepwise mechanism for the following reaction.

What steps are needed to convert benzene into p-isobutyl acetophenone, a synthetic intermediate used in the synthesis of the anti-inflammatory agent ibuprofen.

a. Draw resonance structures for the carbocation formed after loss of a leaving group from phytyl diphosphate.

b. Draw the two-step mechanism for Friedel–Crafts alkylation of 1,2-dihydroxynaphthoic acid with this carbocation to form X.
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