A mechanism for the reaction that occurs in Equation 26-34 is to be proposed. It is to be determined whether the reaction will be as successful if the tert-butyl group were a linear butyl group instead. Concept introduction: To isolate the Poly (ether ether ketone ) or PEEK, the tert-butyl group can be removed from aryl ring by adding excess of toluene in an acidic condition. In this reaction, the tert-butyl group is removed from the aryl ring of PEEK and attached to toluene. The overall reaction is trans tert-butylation, that is, the reaction is reverse of Friedel-Craft alkylation. The removal of tert-butyl takes place through electrophilic aromatic substitution, followed by electrophile elimination, where tert-butyl is eliminated as tertiary carbocation, which then undergoes electrophilic aromatic substitution with toluene. The trans alkylation is possible in this case because of the formation of more stable tertiary carbocation; the reaction would not be possible when the carbocation formed would be a primary one as it is less stable.

Question

Want to see the full answer?

Answer 1

Question

Chapter 26, Problem 26.15P

Interpretation Introduction

Interpretation:

A mechanism for the reaction that occurs in Equation 26-34 is to be proposed. It is to be determined whether the reaction will be as successful if the tert-butyl group were a linear butyl group instead.

Concept introduction:

To isolate the Poly (ether ether ketone) or PEEK, the tert-butyl group can be removed from aryl ring by adding excess of toluene in an acidic condition. In this reaction, the tert-butyl group is removed from the aryl ring of PEEK and attached to toluene. The overall reaction is trans tert-butylation, that is, the reaction is reverse of Friedel-Craft alkylation. The removal of tert-butyl takes place through electrophilic aromatic substitution, followed by electrophile elimination, where tert-butyl is eliminated as tertiary carbocation, which then undergoes electrophilic aromatic substitution with toluene. The trans alkylation is possible in this case because of the formation of more stable tertiary carbocation; the reaction would not be possible when the carbocation formed would be a primary one as it is less stable.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

H- H H H H H H Identify and select all structures below that represent a constitutional isomer(s) of the compound shown above. H- H H H A. H H H H-C CI H H D. H H H H H H C C -H H C C H H H H B. H CI H H- C C H H H H E. H CI H C.

Why doesn't this carry on to form a ring by deprotonating the alpha carbon and the negatively-charged carbon attacking the C=O?

6. A solution (0.0004 M) of Fe(S2CNEt2)3 (see the structural drawing below) in chloroform has absorption bands at: 350 nm (absorbance A = 2.34); 514 nm(absorbance A = 0.0532); Calculate the molar absorptivity values for these bands. Comment on their possible nature (charge transfer transitions or d-d S N- transitions?). (4 points)