Amines
By:
David Eastwood
&
Morgan Gentes
What is an Amine?

Amines are found everywhere. They appear
mainly in decaying animal and plant matter.
Amines are what give off a pungent odour,
mainly being the one we recognize as decaying
flesh. Ironically, amines are also are huge part of
the compositions of perfumes and colognes.
Animals are attracted to the scent of decaying
flesh. Apparently so are humans.
Structure
Amines are a derivative of ammonia
where one or more hydrogen atoms are
replaced by an substituent.
cyclobutyl amine or
cyclobutanamine
Nomenclature
When naming Amines, use the
prefix “amino” and the suffix “amine”.
Lower amines
are named with the suffix amine.
H
H
\
|
N–C–H
/
|
H
H
Methylamine

Since we know that the more
oxidized (bonds to oxygen)
group is the principal group, in
some cases in may not be the
suffix amine used but the prefix
“amino”. In other situations,
H2N
OH
\
/
C-C-C-C
3-amino-1-propanol
RNH2
Primary
Amine
R2NH
Secondary
Amine
R3N
Tertiary
Amine
Ammonia VS. Amine
The chemistry of amines and ammonia are
similar. The most obvious feature is their basicity
(being able to accept a proton) which comes
from the unshared pair of electrons in the
nitrogen atom.
Comparing acceptance of a proton in an
Amine and an ammonia is shown:
H
R\
|
R- N : + H R – N – H
R/
|
R
H
R\
|
R- N : + H R – N – H
R/
|
R

Drawing amines is just as simple as naming
them. “N” represents a locator, just like numbers.

Ex. N-ethyl-3-methyl-1-pentanamine
CH3
N-CH2-CH3
l
/
CH3-CH2-CH-CH2-CH


Draw 1-amino-2-methyl-5-octene-7-ol
OH
NH2
\
/
CH2-CH-C=C-CH-CH2-CH-CH2
|
CH3
Methylamine
http://upload.wikimedia.org/wikipedia/commons/archive/7/7f/20100103095327!Methylamine-2D.png
ethyl amine or
ethanamine
3-amino-2,6-dimethyl-4propyloctane
Prepared Amines
Amines can be prepared by a substitution
process called Alkylation, where an alkyl
group becomes bonded to a Nitrogen.
http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch22/ch22-3-1.html
Reactions
References
www.chem.ucalgary.ca/courses/350/Carey/.../amines/amin
es-1.html
^ McMurry, John E. (1992), Organic Chemistry (3rd ed.),
Belmont: Wadsworth, ISBN 0-534-16218-5
^ Lide, D. R., ed. (2005), CRC Handbook of Chemistry and
Physics (86th ed.), Boca Raton (FL): CRC Press,
ISBN 0-8493-0486-5
^ Karsten Eller, Erhard Henkes, Roland Rossbacher,
Hartmut Höke "Amines, Aliphatic" in Ullmann's
Encyclopedia of Industrial Chemistry, Wiley-VCH,
Weinheim, 2005. doi:10.1002/14356007.a02_001
^ March, Jerry (1992), Advanced Organic Chemistry:
Reactions, Mechanisms, and Structure (4th ed.), New
York: Wiley, ISBN 0-471-60180-2