Advices For Studying Organic Chemistry

H 2 CCH 2 KMnO (^4) OH−, Η 2 2
2 O
HCCH
OH

• cold
  OH
  Ethene 1,2-Ethanediol
  (ethylene glycol)
  CH 3 CH CH (^2) 2. Na
  2 SO 3 /H 2 O or^ NaHSO

1. OsO 4 , pyridine CH 3 CH CH 2
   3 /H 2 O OHOH
   Propene 1,2-Propaneiol
   (propylene glycol)

8.10A MECHANISMS FOR SYN-HYDROXYLATION OF ALKENES

1. The mechanism for the syn-hydroxylation of alkenes:

CC CC OH

−

O

Mn

O

O O−

2

several

steps

+ OHOH

Mn

O O

HO CC + MnO^2

O O−

CCpyridine CC

O

Os

Os O

O

O

O

An osmat

O

O

NaHSO 3

H 2 O CC

OHOH

+ Os

+

O e ester

+ MnO 4 −

OH−

cold

cis-1,2-Cyclopentanediol

H H

HH

O O−

H 2 O HH

(a meso compound)

O

Mn

O HO OH