Zaitsev.

Markov.
Anti-Zaitsev. Zaitsev.
Markov.
Br
NH 2
OH

1)e
xce
2)

tBuOK
ss
Na

HBr

at
CH

he
OH
Markov.

4
3
OH

Br

3O +
3P
H

H
H 2O
Syn addition H2, P ) 2,H
H
d Ac
H g(O H4
1) aB
2) N
Br 2 Br
CH2N 2, heat Anti addition (step2)
CCl 4 Br
Syn addition
OH Br
C l 3, K 2
C H H
2O

1)
2)

BH
(eg mCPBA)
3H

H2
O2
O

3
RCO 3H
3O +

.T
RC

OH

,N

HF
Cl Anti addition (step2)
H

aO
1)

Syn addition
2)

Br

H,
Cl Markov.

H2
O
OH H
OH O
OH

Anti addition (step2) Syn addition

Syn addition
Anti-Markov.
 CH
H2, P

C
d

l 3, K
CH2N 2, heat

OH
2) N
1) aOH
RC
O
1)ex
2) 3H
cess
H CH 3
3O +
Br

RCO 3H tBuOK, heat

(eg mCPBA)
HBr

H
2)
H2
3P
O2 O
4
,N
he
1)
HC
1)

BH
3
aO
l, H at
H

H,
2O
.T H2
HF O or
g(O

H
H
2) N
Ac

3O +
)

2O
Br
2

aB

2
H4

Br 2
, H2

CCl 4
O
 NH 2 Br

OH

OH
H
H

Br

Br

OH
Cl
Cl Br

OH H
OH O
OH