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

Biochemistry
9th Edition
ISBN:9781319114671
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Chapter1: Biochemistry: An Evolving Science
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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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