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

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
icon
Concept explainers
Question
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
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Nomenclature of Organic Compounds
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY