Advices For Studying Organic Chemistry

C

C

HO H

CH 3

H

OH

CH

H

3

C

C

H 3 C OH

H

3 CH OH

(R,R)-2,3-butanediol

syn-hydroxylation

C

C

HO H

CH 3

H OH

CH 3

C

C

O CH 3

H

HO HCH 3

C

C

H CH 3

H 3 C H

trans-2-Butene (S,S)-2,3-butanediol

at either face oftheal

H

kene

Synthesis

C

C

H CH 3

H 3

trans-2-Butene

C H

1. OsO 4


2. NaHSO 3 , H 2 O

C

C

HO H

CH 3

H OH

CH 3

C

C

HO H

CH 3

H OH

CH 3

(R,R) (S,S)

i) nd produces the desired enantiomeric

2,3-butanediols as a racemic mixture (racemate).

2) Synthesis of trans-2-butene:

Enantiomeric 2,3-butanediols

This reaction is stereospecific a

Retrosynthetic Analysis

C

C

H CH 3 CH 3

anti-add on C

C +^2

2-Butyne

iti H

H 3 C H

trans-2-Butene

CH 3

Synthesis