A mechanism for the given reaction is to be suggested. Concept Introduction: Aryl halides (halogens attached to the benzene ring) generally do not undergo nucleophilic aromatic substitution reaction, until and unless there are electronegative atoms present on the ring. An electron withdrawing atom or group attached to the benzene ring imposes the electron-attracting inductive effect and stabilizes the cyclohexadienyl anion intermediate which permits the reaction to proceed rapidly. Nucleophilic aromatic substitution reactions follow an addition-elimination mechanism. In the first step, addition of the nucleophile to aryl halide takes place to form a cyclohexadienyl anion intermediate. In the second step, the elimination of the halide group takes place. Strong electron withdrawing substituents in the aryl halide stabilizes the cyclohexadienyl anion intermediate. Nucleophilic aromatic substitution reactions follow the second order rate law in which the rate of the reaction depends on the concentration of aryl halide and the nucleophile. Presence of strongly electronegative (electron withdrawing) group(s) on the benzene ring activates it towards nucleophilic aromatic substitution.

Question

Want to see the full answer?

Answer 1

Question

Chapter 13, Problem 57P

Interpretation Introduction

Interpretation:

A mechanism for the given reaction is to be suggested.

Concept Introduction:

Aryl halides (halogens attached to the benzene ring) generally do not undergo nucleophilic aromatic substitution reaction, until and unless there are electronegative atoms present on the ring.

An electron withdrawing atom or group attached to the benzene ring imposes the electron-attracting inductive effect and stabilizes the cyclohexadienyl anion intermediate which permits the reaction to proceed rapidly.

Nucleophilic aromatic substitution reactions follow an addition-elimination mechanism.

In the first step, addition of the nucleophile to aryl halide takes place to form a cyclohexadienyl anion intermediate.

In the second step, the elimination of the halide group takes place.

Strong electron withdrawing substituents in the aryl halide stabilizes the cyclohexadienyl anion intermediate.

Nucleophilic aromatic substitution reactions follow the second order rate law in which the rate of the reaction depends on the concentration of aryl halide and the nucleophile.

Presence of strongly electronegative (electron withdrawing) group(s) on the benzene ring activates it towards nucleophilic aromatic substitution.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

These are in the wrong boxes. Why does the one on the left have a lower molar mass than the one on the right?

SYNTHESIS REACTIONS. For the following reactions, synthesize the given products from the given reactants. Multiple reactions/steps will be needed. For the one of the steps (ie reactions) in each synthesis, write out the mechanism for that reaction and draw an energy diagram showing the correct number of hills and valleys for that step's mechanism. CI b. a. Use acetylene (ethyne) and any alkyl halide as your starting materials Br C. d. "OH OH III. OH

Calculate the pH and the pOH of each of the following solutions at 25 °C for which the substances ionize completely: (a) 0.200 M HCl