Advices For Studying Organic Chemistry

11.21A ALKENES IN SYNTHESIS

1. Hg(OAc) 2 , THF-H 2 O HyMarkovnikovdration

BH 3 H^2 O^2

OH−

H Syn addition

of hydrogen

Hydration

Syn hydrogen

H 4 , O

H B H OH

H H

HO H

O

OH

OH

Anti

Hydroxylation

HO

Anti

Hydroxylation

OH

HO

THF:

CH 3 CO 2

2. NaB H−

Me H

Me H Me H

Me H

Me H

( means indefinite stereochemistry)

(Section 11.6

and 11.7)

(Section 11.6

and 11.7)

(Section 11.5)

Me H

RCO 2

Me

H

(Section 11.19)

H

Me

(Section 11.18

and 11.19)

H+/ROH

Me

RO H

OR

H

Me

RO−

H 3 O+

HO

OH

OH−

Figure 11.7 Summary of importrant reactions of alcohols and ethers starting with
ethanol.