• Slides 2 through 4 were part of a series on
the inversion of amines.
Does this amine appear have a stereogenic center if we
don’t limit ourselves C as part of the definition?
H3C
H3CH 2C
N
H
a. No, it has only 3 different “groups” surrounding it.
b. Yes, it has 3 different “groups” surrounding it, and could
be a stereogenic center.
c. No, it has only 4 different “groups” surrounding it.
d. Yes it has 4 different “groups” surrounding it, and could
be a stereogenic center.
• Are they enantiomers?
H
H3C
H3CH2C
N
N
H
a. Yes
b. No
c. not possible to have an enantiomeric
relationship
CH3
CH2CH3
• A 50:50 mixture forms. Will this substance
be optically active?
a. yes
b. no
c. not possible to predict
H-Bonding in Amines
Are 1 amines capable of H-bonding with
themselves?
a. yes
b. no
c. impossible to determine
Amine Structure
Are 3 amines capable of H-bonding with
themselves?
a. yes
b. no
c. impossible to determine
Physical Properties
If an amine is capable of H bonding does
that increase or decrease its m.p. and
b.p. relative to other compounds of
similar polarity and m.w.?
a. increase
c. neither
b. decrease
m.p. C b.p. C
Propane
m.w.
g/mole
44
-189.7
-43
Dimethyl Ether
46
-138.5
-25
Ethanol
46
-117.3
78.5
Dimethylamine
45
-93
7.4
Ethylamine
45
-81
16.6
Trimethylamine
59
-117.2
2.9
Compound