4. ([0]) conditions. Examine the details of the mechanism, paying close attention to the lack of lone pairs, and then respond to the following questions. Note that “reaction arrow" refers to the arrows that separate the reaction steps. (a) Draw a box around the pE2 step (reaction arrow) of the mechanism. (b) Draw a star on any addition (Ad) step (reaction arrow) of the mechanism. (c) Draw a circle around any elimination (E) step (reaction arrow) of the mechanism. (d) When the Swern conditions are characterized as NOT over-oxidizing primary hydroxyl FGs into carboxyl FGs, to what step in the mechanism does this refer? (e) What is the leaving group for the pE2 step in this mechanism? What criteria is used to judge what makes this FG a good leaving group? The given mechanism tracks the transformation of a primary hydroxyl FG into an aldehyde carbonyl using the Swern oxidation CH2 CI-SO CH3 CO2 H3C S=0 + H3C CI H3C H3C CO H3C H3C CIO H3C H3C H3C H. H R98 CH3. H3C H3C H. H R H3C R `R NEt3 H

4. ([0]) conditions. Examine the details of the mechanism, paying close attention to the lack of lone pairs, and then respond to the following questions. Note that “reaction arrow" refers to the arrows that separate the reaction steps. (a) Draw a box around the pE2 step (reaction arrow) of the mechanism. (b) Draw a star on any addition (Ad) step (reaction arrow) of the mechanism. (c) Draw a circle around any elimination (E) step (reaction arrow) of the mechanism. (d) When the Swern conditions are characterized as NOT over-oxidizing primary hydroxyl FGs into carboxyl FGs, to what step in the mechanism does this refer? (e) What is the leaving group for the pE2 step in this mechanism? What criteria is used to judge what makes this FG a good leaving group? The given mechanism tracks the transformation of a primary hydroxyl FG into an aldehyde carbonyl using the Swern oxidation CH2 CI-SO CH3 CO2 H3C S=0 + H3C CI H3C H3C CO H3C H3C CIO H3C H3C H3C H. H R98 CH3. H3C H3C H. H R H3C R `R NEt3 H

Pushing Electrons

4th Edition

ISBN:9781133951889

Author:Weeks, Daniel P.

Publisher:Weeks, Daniel P.

Chapter4: On Solving Mechanism Problems

Section: Chapter Questions

Problem 5EQ

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