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enantiomers
R1
R2
Br2 R1
Br R2 + R1
Br R2 Br (S,S) Br R2 + R1 Br (S,R) R2 enantiomers but when R1 equals R2 then meso, hence they are the same enantiomers
Br (R,R) Br R1 Br (R,S)
R1
R2
Br2
2) anti-addition
mCPBA meso H3O+ OH + OH (R,R) H3O+ R1 OH R2 + R1 (S,S) OH R2 OH (S,S) enantiomers OH OH enantiomers
R1
R2
mCPBA
R1 O
R2 +
R1 O
R2
OH (R,R)
R1
R2
mCPBA R1
R2
O R1
R2
H3O+ R1
OH R2 + R1
enantiomers
OH (R,S)
OH (S,R)
OH (R,R) OH R1 Br (S,S) OH R1 Br R2 + R1
OH (S,S) Br R2
R1
R2
Br2/H2O
(R,S) Br R1 R2 OH (S,R) +
R1
OH (R,S) OH R2
strong base
O R1
R2
O + R1 (S,S) enantiomers
R2
(R,R)
Br (R,S)
Reactions of Alkenes
Radical Bromination
Br Br2 h, AIBN, or peroxides Br NBS h, AIBN, or peroxides
Dehydrohalogenation
Br Strong Base MOR M = Li, Na, K R = Me, Et, etc
t-Bu is best
MNR2 M = Li, Na, K R = Me, Et, etc
Reactions of Alkenes:
continued
OR 1% Strong acid ROH Acid = HCl, H2SO4, H3PO3, RSO3H R = H, Me, Et, etc
NaBH4/O2
OR OH
Reactions of Alkenes:
Oxidations
Epoxidation of alkene
1) Peracids O RCO3H mCPBA Cl CO3H
example (mCPBA)
Dihydroxylation of alkene
1) Osmium Tetroxide (OsO4) OsO4 O O O Os O OH H2O OH + OsO3 OsO3 H2O2 OsO4
2) catalytic Osmium Tetroxide (OsO4) with co-Oxident O O O Os O OH H2O OH + OsO3 co-[O] = H2O2, R3NO, I2, or Fe(III)
1% OsO4 co-[O]
co-[O]
OH NaBH4
Reactions of Alkenes:
Oxidations
Epoxidation of alkenes
O RCO3H 1) Br2/H2O 2) Srong base O (R,S) achiral becasue meso
R1
R2
RCO3H
H R1
H R2
R1
R2
RCO3H
R1
R2
H R2
(+/)
Epoxidation/hydrolysis of alkenes
1) RCO3H 2) H3O+ OH OH (R,R) and (S,S) (+/) 1) RCO3H 2) H3O+ HO R1 (+/) 1) RCO3H 2) H3O+ R1 OH R2 (R,S) and (S,R) achiral when R1=R2 OH R2 R1 OH R2 OH (+/) (R,R) and (S,S)
R1
R2
R1
R2
OH (+/)
Dihydroxylation of alkenes
OH OsO4 OH (R,R) and (S,S) (+/) OsO4 HO R1 (+/) OH R1 R2 OsO4 R1 R2 (R,R) and (S,S) OH R2 R1 OH R2 OH (+/) (R,S) and (S,R) achiral when R1=R2
R1
R2
OH (+/)