(a)
Interpretation:
The base-promoted hydrolysis reaction of a thio-ester is to be compared with that of an oxygen ester. The effect of resonance stabilization of the carbonyl compound on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.
Concept introduction:
In oxygen esters, ester bonds are more stabilized by resonance but it’s not the same in thio-esters although the electronegativity of sulfur is less than oxygen. The thio-ester sulfur being bigger in size does not participate in resonance because overlapping of orbital is not supported.
(b)
Interpretation:
The effect of polar stabilization of the transition state on the base-promoted hydrolysis reaction of a thio-ester and an oxygen ester is to be stated.
Concept introduction:
The electronegativity decrease when we move down a group in periodic table. Sulfur is less electronegative than oxygen. And this is the reason sulfur shows less polarity than oxygen in molecules. Ethylthio-esters are more stable than ethyl ester because of their less polar character. Sulfur being less polar than oxygen atom, polarity in molecule is lesser and therefore transition state is more stable.

Want to see the full answer?
Check out a sample textbook solution
Chapter 21 Solutions
ORGANIC CHEMISTRY SAPLING ACCESS + ETEX
- Draw the products formed when the following alkene is treated with 03 followed by Zn, H₂O. Click the "draw structure" button to launch the drawing utility. draw structure ...arrow_forwardCalculate the pH of 0.600 M solution of CH5N (Kb=4.37 x10-4) Hint: use assumption and check it!arrow_forwardDraw all stereoisomers formed when the following alkene is treated with mCPBA. Be sure to answer all parts. Part 1: How many stereoisomers of the product are possible? 1 Part 2 out of 2 Draw the product of the reaction, including stereochemistry. edit structure ...arrow_forward
- Draw the products formed when the following alkene is treated with 03 followed by Zn, H₂O. Be sure to answer all parts. draw structure ... smaller molar mass product draw structure ... larger molar mass productarrow_forwardComplete the two step reaction show the mechanism for all steps.arrow_forwardIdentify whether the reaction would proceed as a E1 or E2 mechanism.arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY





