TOPIC 2: IUPAC NOMENCLATURE

• Principles of the IUPAC system of nomenclature for organic

compounds
How to name organic compounds using the IUPAC rules

In order to name organic compounds you must first memorize

a few basic names. These names are listed within the
discussion of naming alkanes. In general, the base part of the
name reflects the number of carbons in what you have
assigned to be the parent chain. The suffix of the name
reflects the type(s) of functional group(s) present on (or
within) the parent chain. Other groups which are attached to
the parent chain are called substituents.
ALKANE
• Alkanes - saturated hydrocarbons
The names of the straight chain saturated hydrocarbons for up
to a 12 carbon chain are shown below. The names of the
substituents formed by the removal of one hydrogen from the
end of the chain is obtained by changing the suffix -ane
There are a few common branched substituents which you should
memorize. These are shown below.
Here is a simple list of rules to follow. Some examples are given at the end of the list.

1.Identify the longest carbon chain. This chain is called the parent chain.

2.Identify all of the substituents (groups appending from the parent chain).

3.Number the carbons of the parent chain from the end that gives the substituents the lowest
numbers. When compairing a series of numbers, the series that is the "lowest" is the one which
contains the lowest number at the occasion of the first difference. If two or more side chains are
in equivalent positions, assign the lowest number to the one which will come first in the name.

4.If the same substituent occurs more than once, the location of each point on which the
substituent occurs is given. In addition, the number of times the substituent group occurs is
indicated by a prefix (di, tri, tetra, etc.).

5. If there are two or more different substituents they are listed in alphabetical order using the
base name (ignore the prefixes). The only prefix which is used when putting the substituents in
alphabetical order is iso as in isopropyl or isobutyl. The prefixes sec- and tert- are not used in
determining alphabetical order except when compared with each other.
6. If chains of equal length are competing for selection as the parent chain, then the choice goes in series to:
a) the chain which has the greatest number of side chains.
b) the chain whose substituents have the lowest- numbers.
c) the chain having the greatest number of carbon atoms in the smaller side chain.
d)the chain having the least branched side chains.

7. A cyclic (ring) hydrocarbon is designated by the prefix cyclo- which appears directly in front of the base
name.

In summary, the name of the compound is written out with the substituents in alphabetical order followed by
the base name (derived from the number of carbons in the parent chain). Commas are used between
numbers and dashes are used between letters and numbers. There are no spaces in the name.
ALKENES AND ALKYNES
• Double bonds in hydrocarbons are indicated by replacing the suffix -
ane with -ene. If there is more than one double bond, the suffix is
expanded to include a prefix that indicates the number of double
bonds present (-adiene, -atriene, etc.). Triple bonds are named in a
similar way using the suffix -yne. The position of the multiple bond(s)
within the parent chain is(are) indicated by placing the number(s) of
the first carbon of the multiple bond(s) directly in front of the base
name.
Here is an important list of rules to follow:

1.The parent chain is numbered so that the multiple bonds have the lowest numbers (double
and triple bonds have priority over alkyl and halo substituents).

2.When both double and triple bonds are present, numbers as low as possible are given to
double and triple bonds even though this may at times give "-yne" a lower number than "-ene".
When there is a choice in numbering, the double bonds are given the lowest numbers.

3.When both double and triple bonds are present, the -en suffix follows the parent chain
directly and the -yne suffix follows the -en suffix (notice that the e is left off, -en instead of -ene).
The location of the double bond(s) is(are) indicated before the parent name as before, and the
location of the triple bond(s) is(are) indicated between the -en and -yne suffixes. See below for
examples.
4. For a branched unsaturated acyclic hydrocarbon, the parent chain is the longest carbon
chain that contains the maximum number of double and triple bonds. If there are two or
more chains competing for selection as the parent chain (chain with the most multiple bonds),
the choice goes to (1) the chain with the greatest number of carbon atoms, (2) the # of carbon
atoms being equal, the chain containing the maximum number of double bonds.

5. If there is a choice in numbering not previously covered, the parent chain is numbered to
give the substituents the lowest number at the first point of difference.
CYCLOALKANES, CYCLOALKENES
• Cyclic hydrocarbons are mainly comprised of a chain of carbon atoms that form a
continuous "ring", as opposed to hydrocarbons that have defined ends.
Cycloalkanes are connected entirely by single bonds and cycloalkenes contain
double bonds.
• Cycloalkanes are extremely simple to name; the prefix "cyclo" is affixed to the
regular alkane name corresponding with the number of carbons in the ring. For
example, a cycloalkane comprised of five carbon atoms is named "cyclopentane".
• Cycloalkenes follow the same system, but contain numerical prefixes and infixes
"di" and "tri" if there are two or three multiple bonds within the ring. If there is
only one multiple bond in the ring, numerical prefixes are not needed, as it is
assumed that numeration of the carbon atoms would begin at the carbon atom
with the multiple bond.
For example, consider the compound to the left in the image above. It is a cycloalkene with four carbon
atoms and one double bond, and is simply named "cyclobutene".

With two or more multiple bonds, the naming system is identical to the method used with non-cyclic alkenes.
Each carbon atom is numbered such that the carbon atoms connected by double bonds have the lowest
numbers possible. Each multiple bond is represented by the number of the lowest number carbon that it is
connected to; when numbering, start at 1, a carbon connected to a double bond, and move in the direction of
that double bond when numbering subsequent carbon atoms. Either "di" or "tri" is inserted between the prefix
representing the number of carbon atoms and the term "ene".

For example, consider the compound to the right in the image above. It is a cycloalkene with six carbon
atoms and two double bonds located at opposite ends of the hexagonal "ring". Starting with the number "1" at
an arbitrary carbon atom containing a double bond and numerating clockwise or counterclockwise in the
direction of the initial double bond, the next carbon atom containing the second double bond would be
numbered "4". Therefore, this cycloalkene's name is "1,4 cyclohexadiene".
• a) Cyclohexane
• b) Cyclopentadiene
• c) 1,3,6-cyclooctatriene
DIENES
A diene is a hydrocarbon chain that has two double bonds that may or may not be adjacent to each
other. This section focuses on the delocalization of pi systems by comparing two neighboring double
bonds. The arrangements of these double bonds can have varying affects on the compounds reactivity
and stability.

Naming Dienes
First identify the longest chain containing both carbons with double bonds in the compound. Then give
the lowest possible number for the location of the carbons with double bonds and any other functional
groups present (remember when naming alkenes that some groups take priority such as alcohols). Do
not forget stereochemistry or any other orientation of the double bond such as (E/Z,cis or trans).