Nomenclature of Polyfunctional Organic Compounds

Now with millions of organic compounds being known and several

being created daily,there is a problem in naming them due to the sheer
complexity of their structures.Even chemists often encounter problems
with naming a complex polyfunctional compound.
For Chemical Abstract Servive (CAS) ,each compound must have only
one name ,common names are not allowed .
For chemists , it is best that a chemical name be pronounceable to be easy
to assign and interpret .
Chemists use the nomenclature system devised and maintained by the
IUPAC .
The name of a polyfunctional organic molecule has four parts :
1) suffix 2) parent 3) prefixes 4) locants

1)The Suffix - functional group precedence :

Although an organic molecule might contain several different functional
groups we should choose only one suffix for nomenclature purposes . The
only exception to this rule is when naming compounds with double or
triple bonds.
Functional groups are divided into principal groups and subordinate
groups , principal groups can be cited as prefixes or as suffixes ,an order
of priority has been established so that the principal group of highest
priority is chosen as the proper suffix while subordinate groups are cited
only as prefixes .
Examples:
A keto ester can be named as a ketone -one or as an ester –oate but it
cannot be named as -onoate
Ester group is higher in priority than a ketone as shown in the table.

Methyl 3-(2-oxocyclohex-6-enyl)propanoate
 O O OH
ǀǀ ǀǀ ǀ
CH3CCH2CH2COCH3 CH3CHCH2CH2CH2NH2
1. Methyl 4-oxopentanoate 2. 5-aminopentan-2-ol
[An ester with a ketone group] [ an alcohol with an amine group]

CHO O O OH O
ǀ ǀǀ ǀǀ ǀ ǀǀ
CH3CHCH2CH2CH2COCH3 H2NCCH2CHCH2CH2COH
3. Methyl 5-methyl-6-oxohexanoate 4. 5-Carbamoyl-4-hydroxypentanoic acid
[an ester with an aldehyde group] [a carboxylic acid with amide and alcohol
group]

5. 3-oxocyclohexanecarbaldehyde
[an aldehyde with a ketone group]
2)The parent –selecting the main chain or ring:

A)If the principal group of highest priority is a part of an open chain :

The parent name is the longest chain containing the largest number of
principal groups
Example on isomeric aldehydo amides
Compound 6 the longest chain has six carbons
Compound 7 has a six carbon chain but the longest chain that contains
both functional groups has only 4 carbons
O O CHO O
ǀǀ ǀǀ ǀ ǀǀ
HCCHCH2CH2CH2CNH2 CH3CH2CH2CHCH2CNH2
ǀ
CH3
6. 5-Methyl-6-oxohexanamide 7. 4-oxo-3-propylbutanamide

B)If the highest priority principal group is attached to a ring , the parent
name is that of a ring system:

Example1: isomeric keto nitriles named as nitriles

 Compound 8: -CN group is a substituent on the aromatic ring :
benzonitrile
 Compound 9: -CN group is on an open chain :acetonitrile

8. 2-acetyl-(4-bromomethyl)benzonitrile 9.(2-acetyl-4-bromophenyl)acetonitrile

Example 2: ketoacids named as acids

 Compound 10 parent name is that of a ring system
 Compound 11 parent name is that of an open chain

10.trans-2-(3-oxopropyl)cyclohexane- 11.3-(2-oxocyclohexyl)propanpoic acid

carboxylic acid
3 and 4) prefixes and locants:
Give numbers or locants to all substituents [include all alkyl groups and
all functional groups other than the one cited as suffix] on the parent
chain or ring.
Example :
 Compound 12 contains ( carboxyl,keto,double bond)
The longest chain containing the functional groups has 7 carbons
(heptenoic) ,numbering is from the end nearer the highest priority
functional group .

(2E)-2,5,5-trimethyl-4-oxohept-2-enoic acid

Additional rules :

1. Order of prefixes:
a)Substituents are identified ,b)main chain is numbered,c) multipliers(-di
and -tri) are assigned,the name is written with the substituents listed in
alphabetical rather than numerical order.
Example compound13:

OH
ǀ
H2NCH2CH2CHCHCH3
ǀ
CH3
13. 5-amino-3-methylpentan-2-ol
2.Use of hyphen;single- and multiple-word names:
If the parent is an element or a compound it is written as a single word
otherwise it is written as multiple words
Examples

3.parentheses:
They are used to denote complex substituents
chloromethylbenzene : 2 substituents on a benzene ring
(chloromethyl)benzene: 1 complex substituent
N.B. expression in parentheses is not set off by hyphens from the rest of
the name .