Metal oxo reagents (like OsO4) are well-known to give syn dihydroxylation in their products (1). 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 H3C CH3 CH3 OSO4 НОН 1. MCPBA 2. Н30 H3C H3C OH ОН OH OH CH3 H3C CH3 + H3C OH ОН ОН CH3 CH3

Metal oxo reagents (like OsO4) are well-known to give syn dihydroxylation in their products (1). 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 H3C CH3 CH3 OSO4 НОН 1. MCPBA 2. Н30 H3C H3C OH ОН OH OH CH3 H3C CH3 + H3C OH ОН ОН CH3 CH3

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 9E

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