plan a short synthesis that exploits the use of sulfonate esters as good leaving groups

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
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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plan a short synthesis that exploits the use of sulfonate esters as good leaving
groups

Expert Solution
Step 1
  • Sulfonate- It is salt or ester of sulfonic acid.
  • OH is conjugate base of water. It is strong base and hence a poor leaving group.
  • Good leaving groups are weak base.
  • Alcohol can be converted into good leaving group by converting them into sulfonates.
  • Methanesulfonyl chloride (MsCl) or p-toluenesulfonyl chloride  (TsCl) are some of the reagents that can be used to convert alcohol to suphonates.
  • -OMs or -OTs are weak base and good leaving groups.

 

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