Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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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.
ОН
I
H3C
|| H3C
CH3
CH3
OSO4
НОН
H3C
1. MCPBA
2. H30® HC
ОН
ОН
ОН
ОН
CH3
CH3
H3C
H3C
ОН
ОН
ОН
CH3
CH3
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Transcribed Image Text: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. ОН I H3C || H3C CH3 CH3 OSO4 НОН H3C 1. MCPBA 2. H30® HC ОН ОН ОН ОН CH3 CH3 H3C H3C ОН ОН ОН CH3 CH3
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