Draw a stepwise mechanism for the sulfonium ylide formed from dimethylsulfide and iodomethane. Then, draw the resonance structure of the ylide product. 1.) CH3I Sulfonium Ylide 2.) NaCH2SOCH3

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter19: Eas: Electrophilic Aromatic Substitution
Section: Chapter Questions
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Draw a stepwise mechanism for the sulfonium ylide formed from dimethylsulfide and iodomethane.
Then, draw the resonance structure of the ylide product.
1.) CH3I
Sulfonium Ylide
2.) NaCH2SOCH3
Add curved arrows to show the mechanism of the first
Draw the product of the first step. Be sure to
include the leaving group and any charges.
step. Hint: a S-C bond is formed via an SN2 reaction.
Select Draw Rings More
Select Draw Rings More
Erase
Erase
Draw the overall reaction product. Be sure to include
charges. Hint: draw the sulfonium ylide that results when
a proton is removed by sodium methylsulfinylmethylide
(the conjugate base of DMSO).
Draw the resonance structure of the sulfonium ylide
product. Hint: sulfur may have more than eight
valence electrons.
Select Draw Rings More
Erase
Select Draw Rings More
Erase
Transcribed Image Text:Draw a stepwise mechanism for the sulfonium ylide formed from dimethylsulfide and iodomethane. Then, draw the resonance structure of the ylide product. 1.) CH3I Sulfonium Ylide 2.) NaCH2SOCH3 Add curved arrows to show the mechanism of the first Draw the product of the first step. Be sure to include the leaving group and any charges. step. Hint: a S-C bond is formed via an SN2 reaction. Select Draw Rings More Select Draw Rings More Erase Erase Draw the overall reaction product. Be sure to include charges. Hint: draw the sulfonium ylide that results when a proton is removed by sodium methylsulfinylmethylide (the conjugate base of DMSO). Draw the resonance structure of the sulfonium ylide product. Hint: sulfur may have more than eight valence electrons. Select Draw Rings More Erase Select Draw Rings More Erase
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