Alkene Hydrohalogenation to give Halohydrin Page # 7
H H
nu attack BpO
H
H
C
C
C
H
Is Br Br
Br
H
n o
lossof
H d H
Brominium
Backside
Attack Nu Attack
nucleophilic attack H O H
andthen Bris
pushedtoothersideof
molecule
B'i
i'Br
Hai
H O H
t
it
i
g
OH H
Deprotonation O
H H
Products
Reaction Summary
Regioselectivity
yes Markovnikov
Stereoselectivity
anti addition
Carbocation Rearrangement: NO
racemic
CH 3
Br 2/H2O MBE OH
We Br
H H
nu attack BpO
H
H
C
C
C
H
Is Br Br
Br
H
n o
lossof
H d H
Brominium
Backside
Attack Nu Attack
nucleophilic attack H O H
andthen Bris
pushedtoothersideof
molecule
B'i
i'Br
Hai
H O H
t
it
i
g
OH H
Deprotonation O
H H
Products
Reaction Summary
Regioselectivity
yes Markovnikov
Stereoselectivity
anti addition
Carbocation Rearrangement: NO
racemic
CH 3
Br 2/H2O MBE OH
We Br