S :○ 3-sulfolene (butadiene sulfone) maleic anhydride C4H4O2S 116.13 g/mol C4H2O3 98.06 g/mol xylenes heat H H* H₂O OH heat OH H 4-cyclohexene-1,2- dicarboxylic anhydride C8H8O4 168.16 g/mol 4-cyclohexene-1,2- dicarboxylic acid C8H1004 170.16 g/mol
S :○ 3-sulfolene (butadiene sulfone) maleic anhydride C4H4O2S 116.13 g/mol C4H2O3 98.06 g/mol xylenes heat H H* H₂O OH heat OH H 4-cyclohexene-1,2- dicarboxylic anhydride C8H8O4 168.16 g/mol 4-cyclohexene-1,2- dicarboxylic acid C8H1004 170.16 g/mol
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
Related questions
Question
Propose a reasonable mechanism, using curved arrow notation, for the reaction performed in this experiment.
Your answer should include the following:
(1) Decomposition of the 3-sulfolene
(2) cycloaddition of 1,3-butadiene with maleic anhydride including the HOMO-LUMO interactions
(3) hydrolysis of the anhydride under BASE hydrolysis with NaOH in H2O (consider how this differs from what was done in the experiment)
Check attached image.

Transcribed Image Text:S
:○
3-sulfolene
(butadiene sulfone) maleic anhydride
C4H4O2S
116.13 g/mol
C4H2O3
98.06 g/mol
xylenes
heat
H
H*
H₂O
OH
heat
OH
H
4-cyclohexene-1,2-
dicarboxylic anhydride
C8H8O4
168.16 g/mol
4-cyclohexene-1,2-
dicarboxylic acid
C8H1004
170.16 g/mol
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