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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

Explain why \({{\rm{C}}_{\rm{6}}}{{\rm{H}}_{\rm{5}}}{\rm{C}}{{\rm{H}}_{\rm{2}}}{\rm{C}}{{\rm{H}}_{\rm{2}}}{\rm{Br}}\)is not formed during the radical bromination of \({{\rm{C}}_{\rm{6}}}{{\rm{H}}_{\rm{5}}}{\rm{C}}{{\rm{H}}_{\rm{2}}}{\rm{C}}{{\rm{H}}_{\rm{3}}}\).

For each of the following substituted benzenes: (1) \({{\bf{C}}_{\bf{6}}}{{\bf{H}}_{\bf{5}}}{\bf{Br}}\); (2) \({{\bf{C}}_{\bf{6}}}{{\bf{H}}_{\bf{5}}}{\bf{CN}}\) ; (3) \({{\bf{C}}_{\bf{6}}}{{\bf{H}}_{\bf{5}}}{\bf{OCOC}}{{\bf{H}}_{\bf{3}}}\):

  1. Does the substituent donate or withdraw electron density by an inductive effect?
  2. Does the substituent donate or withdraw electron density by a resonance effect?
  3. On balance, does the substituent make a benzene ring more or less electron-rich than benzene itself?
  4. Does the substituent activate or deactivate the benzene ring in electrophilic aromatic substitution?

Label each compound as more or less reactive than benzene in electrophilic aromatic substitution.

Question: Draw a stepwise mechanism for the following reaction.

Which halides are unreactive in a Friedel鈥揅rafts alkylation reaction?
See all solutions

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