organic chemistry 212
ORGANIC CHEMISTRY 212 Lecture 15: October 20th, 2009
Youla S. TSANTRIZOS Office: Chemistry Department Pulp & Paper, Room 108 Email: [email protected]
ORGANIC CHEMISTRY 212/211 – Midterm 1
ORGANIC CHEMISTRY 212/211 – Midterm 1 OH
NaOH I
heat
ORGANIC CHEMISTRY 212/211 – Midterm 1 OH
NaOH I
heat
ORGANIC CHEMISTRY 212 Chapter 7 and 8: ALKENES - the E / Z naming system - Synthesis via Elimination reactions - Hydrogenation - Addition of Halogenation - Addition of Hydrogen Halides - Oxidation
Types of Reactions with Alkenes CH3 CH3 H H2 halogenation
X2
HX X = Cl, Br, I
C
C
H
H
H
Types of Reactions with Alkenes
[O] cyclopropanation
[CH2]
CH3 CH3 H
C
C
OH OH
H
Epoxidation of Alkenes [O]
Acids:
Peroxyacids: O O O
H
O Cl
O O
meta-chloroperoxybenzoic acid MCPBA
H
Epoxidation of Alkenes
O O
H O
Cl
Epoxidation of Alkenes
EPOXIDE
O
H
O
H
O O
O
Cl
Cl
Aflatoxin B1 O
the epoxide of aflatoxin B1can cause hepatic necrosis and liver carcinoma O
O
O
Cytochromo P450 enzymatic oxidation
O
O
O
O
O O
Aspergillus fungi
O
O
O
DNA Intercalation of Aflatoxin B1 Epoxide O
O
O
O
O O
O
Aflatoxin O
O
O
O
O O
intercalation into DNA
O
Aflatoxin O
O
O
O
O O
Major DNA Adduct
O
Guanine (Nucleoside is Guanosine)
Reactions of Epoxides H O H 3C
C H
C
H3C
CH3
C
C
H
H
H2O
H
CH3
H
H
anti addition
H3C
+O
CH3CO2H
H
O
C
C
O
H
CH3
H Diol (or glycol)
H3C
H
H
O
C
C
+O
H H
CH3
Back-side attack by H2O
Types of Reactions with Alkenes
[O] cyclopropanation
[CH2]
CH3 CH3 H
C
C
OH OH
H
Types of Reactions with Alkenes OsO4
Osmium Tetroxide Hydroxylation
Period Table
Types of Reactions with Alkenes H3C H
C
CH3 C H
O
O Os
O
O HOOH
Reactions with Alkenes What product(s) would you get from the reactions below?
Youla S. TSANTRIZOS Office: Chemistry Department Pulp & Paper, Room 108 Email: [email protected]
ORGANIC CHEMISTRY 212/211 – Midterm 1
ORGANIC CHEMISTRY 212/211 – Midterm 1 OH
NaOH I
heat
ORGANIC CHEMISTRY 212/211 – Midterm 1 OH
NaOH I
heat
ORGANIC CHEMISTRY 212 Chapter 7 and 8: ALKENES - the E / Z naming system - Synthesis via Elimination reactions - Hydrogenation - Addition of Halogenation - Addition of Hydrogen Halides - Oxidation
Types of Reactions with Alkenes CH3 CH3 H H2 halogenation
X2
HX X = Cl, Br, I
C
C
H
H
H
Types of Reactions with Alkenes
[O] cyclopropanation
[CH2]
CH3 CH3 H
C
C
OH OH
H
Epoxidation of Alkenes [O]
Acids:
Peroxyacids: O O O
H
O Cl
O O
meta-chloroperoxybenzoic acid MCPBA
H
Epoxidation of Alkenes
O O
H O
Cl
Epoxidation of Alkenes
EPOXIDE
O
H
O
H
O O
O
Cl
Cl
Aflatoxin B1 O
the epoxide of aflatoxin B1can cause hepatic necrosis and liver carcinoma O
O
O
Cytochromo P450 enzymatic oxidation
O
O
O
O
O O
Aspergillus fungi
O
O
O
DNA Intercalation of Aflatoxin B1 Epoxide O
O
O
O
O O
O
Aflatoxin O
O
O
O
O O
intercalation into DNA
O
Aflatoxin O
O
O
O
O O
Major DNA Adduct
O
Guanine (Nucleoside is Guanosine)
Reactions of Epoxides H O H 3C
C H
C
H3C
CH3
C
C
H
H
H2O
H
CH3
H
H
anti addition
H3C
+O
CH3CO2H
H
O
C
C
O
H
CH3
H Diol (or glycol)
H3C
H
H
O
C
C
+O
H H
CH3
Back-side attack by H2O
Types of Reactions with Alkenes
[O] cyclopropanation
[CH2]
CH3 CH3 H
C
C
OH OH
H
Types of Reactions with Alkenes OsO4
Osmium Tetroxide Hydroxylation
Period Table
Types of Reactions with Alkenes H3C H
C
CH3 C H
O
O Os
O
O HOOH
Reactions with Alkenes What product(s) would you get from the reactions below?
