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The decomposition of various substituted benzyl azoxyarenesulfonates in trifluoroethanol was studied. The overall reaction is shown below

The decomposition of various substituted benzyl azoxyarenesulfonates in trifluoroethanol was studied. The overall reaction is shown below

Biochemistry
Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
Problem 1P
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The decomposition of various substituted benzyl azoxyarenesulfonates in trifluoroethanol was studied. The overall reaction is shown below F3C OH CF3 HO,S + N20 The decomposition of various substituted benzyl azoxyarenesulfonates in trifluoroethanol was studied. The overall reaction is shown below F,C OH HO,S + N,0 Y kobs (S ') 3-CI CH3 3.1 x 10-7 4-CI CH3 2.3 х 10-6 3-CH3 4-CH3 4-OCH3 CH3 CHs 4.7х 10-6 CH3 7.6х 10-6 CH3 6.0 x 10-5 1.7 x 10-3 4-CH OCH3 4.24 x 10-5 4-CH3 4-CH3 4-CH3 CH3 Br 6.0 x 10-5 1.91 x 10-4 CN 4.65 x 10-4 a. Using the data provided, prepare Hammett plots to quantify the effects of the substituents X and Y on the reaction's rate. Attach them to your problem set. b. Based on your Hammett analysis, propose a complete, curved-arrow mechanism for this reaction. Use a sentence or two to explain how your Hammett analyses support your proposed mechanism.
Transcribed Image Text:The decomposition of various substituted benzyl azoxyarenesulfonates in trifluoroethanol was studied. The overall reaction is shown below F3C OH CF3 HO,S + N20 The decomposition of various substituted benzyl azoxyarenesulfonates in trifluoroethanol was studied. The overall reaction is shown below F,C OH HO,S + N,0 Y kobs (S ') 3-CI CH3 3.1 x 10-7 4-CI CH3 2.3 х 10-6 3-CH3 4-CH3 4-OCH3 CH3 CHs 4.7х 10-6 CH3 7.6х 10-6 CH3 6.0 x 10-5 1.7 x 10-3 4-CH OCH3 4.24 x 10-5 4-CH3 4-CH3 4-CH3 CH3 Br 6.0 x 10-5 1.91 x 10-4 CN 4.65 x 10-4 a. Using the data provided, prepare Hammett plots to quantify the effects of the substituents X and Y on the reaction's rate. Attach them to your problem set. b. Based on your Hammett analysis, propose a complete, curved-arrow mechanism for this reaction. Use a sentence or two to explain how your Hammett analyses support your proposed mechanism.
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