Advices For Studying Organic Chemistry

5. Specific examples:

CH 3 (CH 2 ) 2 CH CH 2 Hg(OAc)^2

OAc

CH 3 (CH 2 ) 2 CH CH 2

Hg

NaBH 4

+

1-Pentene

2-Pentanol (93%)

THF- OH−

(1 h)

CH 3 (CH 2 ) 2 CH CH 2 Hg

H

(15s) OH

H 2 O

OH

C

CH 3

C

HO HO

H 2 O

CH 3

C

CH 3

1-Methylcyclo-
pentene

1-Methylcyclo-

pentanol

Hg Hg H

THF-

NaBH 4

OH−

(6 min)

+ Hg

(20s) HH

(OAc) (^2) OAc

6. Rearrangements of the carbon skeleton seldom occur in oxymercuration-
   demercuration.
   
   
   1. Hg(OAc) 2 /THF-H 2 O
   
   
   
   

OH

CH 3 CCHCH (^2) 2. NaBH 4 , OH− CH 3 CCH
CH 3
CH 3 CH 3
CH 3
3,3-Dimethyl-1-butene 3,3-Dimethyl-2-butanol
(94%)
C
H
H
H

1. 2,3-Dimethyl-2-butanol can not be detected by gas chromatography (GC)
   analysis.


2. 2,3-Dimethyl-2-butanol is the major product in the acid-catalyzed hydration of
   3,3-dimethyl-1-butene.

7. Solvomercuration-demercuration:

CC NaBH^4 , OH−

CC

OR OR

Hg

CC

O 2 CCF 3 H

Alkene (Alkoxyalkyl)mercuric

trifluoroacetate

Hg

solvomercuration

Ether

demercuration

(O 2 CCF 3 ) 2 /THF-ROH