6B1: Recognize and apply the pathway of syn addition with larger atoms via three-membered transition state followed by Sx2 to solve synthetic problems. Metal oxo reagents (like OsO4) are well-known to give syn dihydroxylation in their products (I). This is in contrast to use of a peroxy acid reagent (like mCPBA), which when added with strong acid in the 2nd step, gives anti looking dihydroxylation products (II). Draw a detailed, electron-pushing mechanism that shows the formation of the anti looking products using the AE then SN2 mechanistic pathway. OH I H3C || HAC CH3 CH3 OSO4 НОН 1. mCPBA H3C OH OH OH 2.С OH CH3 т H3C + 3 H3C он OH OH CH3 CH3

6B1: Recognize and apply the pathway of syn addition with larger atoms via three-membered transition state followed by Sx2 to solve synthetic problems. Metal oxo reagents (like OsO4) are well-known to give syn dihydroxylation in their products (I). This is in contrast to use of a peroxy acid reagent (like mCPBA), which when added with strong acid in the 2nd step, gives anti looking dihydroxylation products (II). Draw a detailed, electron-pushing mechanism that shows the formation of the anti looking products using the AE then SN2 mechanistic pathway. OH I H3C || HAC CH3 CH3 OSO4 НОН 1. mCPBA H3C OH OH OH 2.С OH CH3 т H3C + 3 H3C он OH OH CH3 CH3

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...

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Organic chemistry student Everett has set up two separate electrophilic addition reactions with 2-butyne (shown below). In reaction (i) the alkyne is treated with 1 equivalent of HBr, which successful provides (Z)-2-bromo-2-butene. In reaction (ii) the alkyne is subjected to a two-step hydroboroation/oxidation sequence. Interestingly, Everett’s second reaction fails to provide the desired methyl ketone and instead has provided butan-2,3-diol. (a) Provide the structure of intermediate X form the first step of reaction (ii). (b) Briefly explain (use structures if necessary) why reaction (i) provided an alkene where as reaction (ii) provided an alkane when only 1 equivalent of the electrophile was used in each reaction.
Please show mechanism
supply mechanisms for the following reactions showing all intermediates, all formal charges, and use arrows to show electron flow
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