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General
formula
Name
Name
suffix
-al
Aldehyde
Name
General
formula
O
Ester
Ketone
Acid
anhydride
R'
Carboxylic
acid
Acid
halide
-one
-oyl
halide
X=halogen
O
R
O
O
Lactone
(cyclic ester)
-oic
acid
-oic
anhydride
R
Name
suffix
-oate
O
O
C
R'
Amide
Lactam
(cyclic amide)
-amide
R'
R"
O
C
R'
hydrophobic
hydrophilic
CO2H
omega-3-fatty
acid
H2O
H2O
H2O
grease
OH
H2O
H2O
OH
glycerol
a triol
OH
H2O
MICELLE
O
O
LIPID BILAYER
O
O P O
O
NH3
Phosphatidylcholine
OH
NH2
a
OH
H2N
OH
H2N
glycine
alanine
OH
H2N
OH
H2N
phenylalanine
OH
H2N
glutamic acid
asparagine
Five of the 20 amino acid building blocks that go into all proteins
All a-amino acids
N
H
H
N
N
H
CO2H
b -Lactam Antibiotics
H2N
Other Penicillins
varied at this
position
H H
N
HO2C
g-lactam
NH
Penicillin G
d-lactam
NH
NH
HO2C
b-lactam
H2N
6-Aminopenicillamic acid
OH
O
b-amino acid
H2N
H2N
b
a
OH
g-amino acid
OH
O
d-amino acid
R2
R1
R1
OH
Na2Cr2O 7
H 2SO4
OH
R1
R1
R2
R2
1. R2MgBr
2. pH7
R1
OH
2. From alkynes
O
2+
R1
Hg , H2 O
H2 SO 4
R1
Me
R1
1. RBH2
2. H2 O2, NaOH
R1
O
R
AlCl3
4. Ozonolysis
1. O3
2. Zn/H3O+
A.
R
-O
Nu
H3O+
HO
R'
Nu
Section 19.8
HO
CH3MgBr +
Section 19.7
HO
CN
HCN
H
Nu
H2O
HO
OH
OH
HO
H3O+
Section 19.11
Section 19.6
O
R
OH OH
Electrophilic at C
No longer electrophilic at C
OH
R
HO
OH OH
HO
OH OH
HO
H2O
Protected (masked)
aldehyde
H
Br
O
OH OH
BrMg
O
H
Br
M go
Mgo
H
BrMg
electrophile
O
O
1.
2. pH7
H
OH
H2O/H+
OH
CH3-Br
BuLi
P
CH3
CH2
triphenyl phosphine
Ph3P
Wittig Reaction
Section 19.12
Ph3PO
CH2
Ph = Phenyl
B.
R
-O
Nu
H3O+
H2O
Nu
Nu
R
R'
Nu
R'
O
NH2
H2O
H3O+
NH
H
H2N
H
N
H2O
NH
NH
Section 19.9
HO
KMnO4
HO
O
2.
O
R'
H
OH
H
R
3.
Jones Oxidation
OH
CO2
R
OH
-O
Nu
Y
Nu
Y
Nu
Y = Leaving Group
LiAlH4
OR
RO-Li+
LiAlH4
H
O
OR
nucleophilic substitution
MeMgBr
OH
nucleophilic addition
RO-Li+
nucleophilic substitution
MeMgBr
Me
OH
Me
Me
nucleophilic addition
OH
Cl
OH
SOCl2
OEt
CH3CH2OH
HCl
Cl
NHR2
NR2
Example:Amide
Section 21.7
H
must have "a " H
(pKa 10-20)
E+ =
electrophile
enolate
O
E
OH
OH
enol
OH
Br2
O
Br
LDA (base)
OLi
Alpha Alkylation
Section 22.8
O
CH3I
LDA =
Li
N
base
R'
OH
R'
R''
R''
Aldol Reaction
O
Section 23.2-23.7
OH
base
O
H
CH3
H3C
Claisen Condensation
O
EtO
C
H2
Section 23.8-23.9
base
CH3
H3C
CH2
EtO
CH2
H3C
H3C
OEt
C
H2
OEt -
OEt
Michael Reaction
O
EtO
Me
NaOEt
EtO
O
Me
EtO
Me
HOEt
Me
H
Me
O
EtO
Me
H
H
O
H
Me