CHEM 3418 and CHEM 3428

Organic Chemistry Nomenclature

Introduction

In the early days of organic chemistry, chemicals often received names based on the sources from which they were
derived. Formic acid, for instance, was derived from the Latin word for ant, formica. Formic acid is the smallest
carboxylic acid and is present in the substance delivered to victims of ant bites and bee stings. Another example is wood
alcohol, also known as methanol. Methanol originally was obtained through the distillation of wood. Names like
methanol and formic acid are called common names.

In the last century, advancement in the field of organic chemistry has produced numerous chemicals, many of which are
difficult to isolate naturally. The naming of organic molecules could no longer rely on the ‘natural’ naming precedent.
With so many molecules being synthesized, a convention had to be established to systematically name a molecule.
Several groups began meeting in the early 20 century to begin mapping out a naming convention. In 1918, the
th

International Union of Pure and Applied Chemistry (IUPAC) was formed and developed the rules for naming molecules.
The rules get updated on a regular basis.

Chains and Branches

The best place to start is to learn the names of the straight chain alkanes. An alkane is a molecule consisting of only
carbon and hydrogen linked together by single bonds. A common term you may have heard is that of hydrocarbon.
Alkanes are a subset of hydrocarbons. A hydrocarbon is composed of only carbon and hydrogen but can have single
double, triple carbon-carbon bonds or aromatic rings. A straight chain alkane is an alkane making only one or two bonds
to neighboring carbons. An alkane with branches is known as a branched alkane. The notion of straight chain vs.
branched alkanes is evident graphically.

The following are the names and chemical drawings for the straight-chain alkanes consisting of 1 to 5 carbon atoms.
The names of alkanes with 6-10 carbon atoms are listed in the right column. The first four; methane, ethane, propane
and butane are derived from common names, the remaining names are derived from Latin numbering followed by ‘-ane’.
It is best to memorize these 10 names and especially the first 6.

Methane Hexane
Ethane Heptane

Propane Octane

Butane Nonane

Pentane Decane

A note on the chemical drawing: Each node (connection of two lines and end of lines) represents a carbon atom. In the
diagram on the left below we have two line segments intersecting: one carbon on each end and one for the intersection
for a total of three carbons). Each carbon atom is assumed to be saturated (saturated means that the maximum number of
hydrogens are present per carbon atom) with hydrogens. Since each carbon can make 4 bonds, for those carbons making
one bond to another carbon, 3 hydrogens are assumed to be present. For those carbons making two bonds to other
carbons, 2 hydrogens are assumed to be present.

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is equivalent to

Notice how the assumption of hydrogen presence makes a much less cluttered representation. This is exactly the goal. It
takes some getting used to the convention and when learning how to draw as it is easy to miss hydrogens or miscount
carbons.

Naming Branches

There are several rules used to systematically name a branched alkane. Branches are attached to a straight-chain alkane.
These branches are often abbreviated as -R.

If you were to name a branch attached to a straight chain alkane, you would count the number of carbons in that branch
and match it to the name of its corresponding straight-chain alkane. To get the branch name, replace the ‘ane’ of the
name with ‘yl’. For instance:

Systematically Naming an Alkane

1. Determine the number of carbons in the longest continuous chain

In this example, there are 6 carbons in the longest continuous chain. The longest continuous chain is referred to as the
parent alkane. The parent alkane in this example is hexane.

2. The name of the branch is cited before the name of the parent hydrocarbon with a number to designate which carbon
it is attached to.

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3. Number the chain so that the branch gets the lowest number possible. The lowest possible numbers are used to
correctly name the alkane when multiple branches are present. Also, if there are two or more of the same branches, the
prefixes ‘di’ and ‘tri’, are used to designate the number attached.

NOT

2,3-dimethylhexane NOT 4,5-dimethylhexane

4. If more than one type of substituent list substituents in alphabetical order

5. When both directions indicate the same low number for one of the branches, the direction is chosen that gives the
lowest possible number to the remaining branches.

NOT NOT
2,4,4-trimethylpentane 5-ethyl-2,6-dimethylheptane

6. If a tie in either direction, the first group alphabetically gets the lowest number.

3-ethyl-4-methylhexane

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NOT
4-ethyl-3-methylhexane

7. If a compound has two or more chains of the same length, the parent hydrocarbon is the chain with the greatest
number of branches.

NOT
3-isopropylhexane

Notes:

• A number and a word are separated by a hyphen; numbers separated by a comma

• Di, tri, tetra etc.… are ignored when alphabetizing.

Cycloalkanes

It is possible to link carbon atoms together in a circular manner. If the molecule is circular and possesses only carbon
and hydrogen with single bonds between them, the molecule is known as a cycloalkane.

The rules to name a cycloalkane are like the rules to name an alkane.

1. Count the number of carbons in the ring to determine the base name.

2. If there is only one branch it is always assumed to be attached to carbon 1. The 1- does not have to be part of the
name although you can put the number 1 in the name. The branch is named following the conventions described above
and the base is a cycloalkane rather than an alkane.

3. If there is more than one branch the numbering starts in alphabetical order. Every substituent now needs a number.

4. If a branch has more carbons than the cycloalkane, then the cycloalkane becomes the branch and is named following
the branch naming conventions described earlier.

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Alkenes

Alkenes are molecules of hydrogen and carbon that possess ONE double bond between carbons. Rather than an ‘–ane’
ending alkenes end with ‘–ene’. As with alkanes, the base name is determined by finding the longest continuous carbon
chain that contains the carbon-carbon double bond. The double bond receives the lowest possible number and that
number signifies the starting carbon of the double bond.

Double bonds take priority over alkyl groups.

Cycloalkenes are named following cycloalkane rules. No numbers are required as it is assumed that the double bond is
between C-1 and C-2. If a CH group is bonded directly to a ring the double bond is the branch and is called a
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methylene.

Alkynes

The usual IUPAC rules are followed. Like alkanes and alkynes, to name an alkyne, the –ane ending is switched with –
yne. To find the base name, find the longest continuous carbon chain containing the triple bond. The triple bond should
be given the lowest number on the chain and signifies the start of the bond. Acetylene is a well-used common name for
ethyne.