CHEM211
Problem Set: Alkenes II
1. Give the organic products for the following reactions. When mixtures are formed, indicate the major product.
OH
Br
*
Br2
CCl4
Cl2
Br
HCl
cis
and
trans
Cl
HO2C
CO2H
Br
Br
Br2
HO2C
HBr
HO2C
peroxides
H2
HO2C
Br HO2C
CCl4
HO2C
Br HO2C
H2
+
10% Pd/C
H
OH
2) NaHSO3, H2O
OH
1) Hg(OAc)2, H2O *
O
2) NaBH4
HCl
Br
1 equivalent
Cl
Cl
H2SO4
Cl
Cl
H2O
O
H
+
Zn(Cu)
HO
HO
1) Hg(OAc)2, H2O *
O
+ CH2O
*
2) Zn, H3O+
H
O
CH2I2
1) BH3
H2SO4
HO
H2O
OH
2) H2O2
H
OH
H +
H
OH
O
See McMurry for mechanisms.
Cl
Cl
OH
KOH
Br2
*
OH
HO
Br
H2O
*
OH
Br
peroxides
IN3
O
2. Write a mechanism for each problem notated with an *.
OH
2) H2O2
HBr
OH
KMnO4
H3O+
H
OH
*
2) NaHSO3, H2O
*
*
CHCl3
*
1) OsO4
Zn(Cu)
cis &
trans
2) NaBH4
Cl
HO
1) BH3
H2
CH2I2
Cl
*
*
10% Pd/C
2) Zn, H3O+
OH
HI
Br
O
1) O3
+
OH
*
both cis and trans
H3O+
1) OsO4
OH
I
+
KMnO4
H
Br
Br
Br
Br
1) BH3
2) H2O2
Br2
HBr
HO
2) NaBH4
Br
Br
excess
10% Pd/C
CO2H
HO2C
CO2H
HO2C
CCl4
Br
1) O3
1) Hg(OAc)2, H2O *
H2O
*
Cl2
Cl
*
Br
N3
I