CHEM 109A CLAS

Reactions of Alkenes
Reagent(s) Groups Interm Regiochemistry Example of Regiochemistry Stereochemistry Example of Stereochemistry
that add ediate (Syn or Anti)
H
H
H2
H2 or D2 w/
Concer H2 Pd/C
Pt/C or Pd/C -H and -H N/A H Syn
ted
or Ni
Pt/C
H
H
OH
OEt H 2O
-H and EtOH Non-
H2O or ROH Carboc
OH or Markovnikov H stereoselective H 2SO 4
w/ H2SO4, HCl ation* H 2SO 4 OH
OR (Syn and Anti)
H

H
OMe
1. Hg(OAc)2, Cyclic
-H and
H2O or mercuri -OH or -OR adds 1. Hg(OAc)2, MeOH
-OH or H Anti 1. Hg(OAc)2, H2O
ROH nium Markovnikov
-OR
2. NaBH4 ion 2. NaBH4
2. NaBH 4
OH

None, H
1. BH3, THF H
-H and 1st step 1) BH 3, THF
2. NaOH, Anti-Markovnikov Syn H
OH concert 2) H2O2, H2O, NaOH OH
1) BH 3, THF
H2O2, H2O
ed
2) H 2O 2, H 2O, NaOH OH

OH
H
Cl
Br H Cl
Hydrogen H Br Non-
Carboc
Halide (HCl, -H and X Markovnikov H stereoselective
ation* Cl
HBr, HI) (Syn and Anti)
H

* Watch for carbocation rearrangement Page 1 of 2

CHEM 109A CLAS
Reactions of Alkenes
Reagent(s) Groups Interm Regiochemistry Example of Regiochemistry Stereochemistry Example of Stereochemistry
that add ediate (Syn or Anti)
H Cl H Cl
H Cl

Hydrogen H
Halide (HCl, H Br Non-
Carbon
HBr, HI) w/ -H and -X Anti-Markovnikov Br stereoselective
radical H H
peroxide H 2O 2 (Syn and Anti) Cl Cl
(H2O2)

Cl2 or Br2
Br2
w/ CH2Cl2, Cl
Cyclic Cl2
benzene CH 2Cl2
-X and X haloniu N/A Cl Anti
(nonpolar
m ion CH2Cl2 Br Br
aprotic
solvent)
Br Br
Cl OMe
Cl2 or Br2 Br2 HO Cl2
w/H2O or -X and Cyclic
-OH or -OR adds Br
ROH OH or haloniu Anti
Markovnikov H 2O MeOH
(protic OR m ion
solvent)
OMe Cl

* Watch for carbocation rearrangement Page 2 of 2