SYSTEMATIC NOMENCLATURE
13
NMe 2
O
O
1-benzyl-3-dimethylamino-2-methyl-1-phenylpropyl
propionate (dextropropoxyphene)
• main chain of acid is propane (C 3 )
main chain of alcohol is propane (C 3 )
these are numbered separately (the ester has two
separate words)
• put in substituents on alcohol component
1
2
• no substituents on acid component
phenyl
Me 2 N
dimethylamino
1
2
OH
• this is an ester (two words, -yl -oate)
the -oate part refers to the acid component, the -yl
part to the esterifying alcohol
OH
O
3
propionic acid
propanoic acid
3
propanol
O
O
propyl propionate
propyl propanoate
benzyl
1 2
OH
3 NMe 2
• join with acid component via ester linkage
1 2
O
3 NMe 2
O
dextropropoxyphene
1-phenyl; 1-benzyl; 2-methyl; 3-dimethylamino
CO 2 H
2-[4-(2-methylpropyl)phenyl]propanoic
acid (ibuprofen)
• main chain is propane (C 3 )
number it
1
2
• main functional group
is an acid (-oic acid)
this will be carbon-1
1
2
3
4
5
6
3
1 2
3
HO
O
1
2
3
HO
O
2-phenylpropanoic
acid
propyl
2-methylpropyl
3
2
1
4-(2-methylpropyl)phenyl
HO
O
ibuprofen
• put in substituents
consider brackets;
we have square brackets
with curved brackets inside
initially ignore the contents
of the curved brackets and
its numbering (4);
this reduces to 2-[phenyl]
propanoic acid, which indicates
phenyl at position 2 on propanoic acid
4-(2-methylpropyl)phenyl = 2-methylpropyl
at position 4 of the phenyl;
2-methylpropyl = propyl with methyl at position 2
note the brackets separate different substituents
and their individual numbering systems