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
Chapter1: Numerals And Fractions
Section: Chapter Questions
Problem 5RP
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)
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