Naming of Organic

Compounds
 LECTURE 10
NAMING OF HYDROCARBONS
I. Alkanes
II. Cycloalkanes
III. Alkenes and
Cycloalkenes IV. Alkynes
V. Aromatic Hydrocarbons
Naming Organic Compounds

Organic compounds are named

according to the IUPAC
(international union of pure & applied
chemistry) system of nomenclature.

Alkanes – end in ane

Alkenes – end in ene

Alkynes – end in yne

Alkenes – CnH2n
series of unsaturated hydrocarbons
having one double bond (C=C)

• Also called ethyle

ne series (IUPAC
name is ethene)
• General formula
CnH2n
Alkenes

• C2H4 = Ethene
• C3H6 = Propene
• C4H8 = Butene
• C5H10 = Pentene
• To find the number of
hydrogens, double th
enumber of carbons.
1-Butene
This is 1-butene, because the
double bond is between the 1st
and 2nd carbon from the end.

ISOMERS: Molecules have the

same molecular formula, but
have different structural
formulas.
Pentene

This is 1-pentene. The

double bond is on the
first carbon from the end.

This is not another isomer

of pentene. This is also 2-
pentene, just that the double
bond is closer to the right
end.
Alkynes –
a series of unsaturated
hydro carbons that contain 1
triple bond.
• Also called the acetylene series

▪
General formula CnH2n-2

C C
Alkynes

• C2H2 = Ethyne
• C3H4 = Propyne
• C4H6 = Butyne •
C5H8 = Pentyne
Alkyl Groups – have one less hyd rogen th
the corresponding alkane.

• CH3 is methyl – one less H

tha n methane,CH4
H
HC H

H
Draw methyl
▪
C2H5 is ethyl – one less H than ethane C2H6

Condensed
Formula:
CH2CH3

Ethane
▪
C3H7 is propyl – one less H than
propane C3H8

propane
Benzene – a series of cyclic
unsaturated hydrocarbons.
▪ General formula CnH2n-6
Benzene – C6H6 the simplest in
the family

C
C C H
C
H C H
C
H
I. Nomenclature of
ALKANES
IUPAC Nomenclature of ALKANES

The IUPAC System of Nomenclature With

the isolation and preparation of thousands
of new organic compounds it became
obvious that each organic compound must
have an unambiguous name. A systematic
method of naming compounds (a system of
nomenclature) was developed by the
International Union of Pure and Applied
Chemistry. It is referred to as the IUPAC
system of nomenclature.
The parent name indicates the number
of carbons in the longest continuous
carbon chain in the molecule.
The suffix indicates what functional group is
present.
The prefix tells us the identity, location,
and number of substituents attached to the
carbon chain.
Naming Substituents
Carbon substituents bonded to a long carbon
chain are called alkyl groups.
To name an alkyl group, change the -ane
ending of the parent alkane to -yl. Thus,
methane (CH4) becomes methyl (CH3–) and
ethane (CH3CH3) becomes ethyl (CH3CH2–).
How To Name an Alkane Using the IUPAC System

Step [1] Find the parent carbon chain and add the
suffix.
Find the longest continuous carbon chain, and
name the molecule using the parent name for that
number of carbons. To the name of the parent, add
the suffix -ane for an alkane. Each functional group
has its own suffix.
7 6 5 4 3 2 1
CH3- CH2- CH2– CH – CH – CH - CH3
CH2 CH3 CH3 CH3

Step 1: Find the longest

continuous chain of carbons.
All bonds in the chain of carbons
are single bonds so ending is…ane.
There are 7 continuous carbons,
so the parent chain is heptane.
 Sometimes the hydrocarbon chains are
not straight and sometimes they have
other elements attached to them. Here is
how they are named:
The longest chain may not be written horizontally across the
page. Remember that it does not matter if the chain is
straight or has bends. All of the following representations are
equivalent.

CH3- CH2- CH2– CH – CH – CH - CH3

CH2 CH3 CH3
CH3
The longest chain may not be written
horizontally across the page.
Remember that it does not matter if
the chain is straight or has bends. All
of the following representations are equivalent.
7 6 5 4 3 2 1
CH3- CH2- CH2– CH – CH – CH - CH3
1 2 3 4 5 6 7
CH2 CH3 CH3
CH3
• Step 2: Number the carbons in
the main sequence starting with
the end that will give the attached
groups the smallest #.
This chain is numbered from right
to left because there is a
substituent closest to the right.
7 6 5 4 3 2 1
CH3- CH2- CH2– CH – CH – CH - CH3
CH2
CH3 CH3
CH3
• Step 3 : Add numbers to the names
of the groups to identify their positions
on the chain.
- these numbers become prefixes to the
parent chain. ethane
yl

In this ex. the positions are: C2H6

5

2 - methyl, 3- methyl, 4 - ethyl

Step [3] Name and number
the substituents.
Name the substituents as alkyl groups, and use the
numbers from step [2] to designate their location.
• Every carbon belongs to either the longest chain or
a substituent, but not both.
• Each substituent needs its own number.
• If two or more identical substituents are bonded to
the longest chain, use prefixes to indicate how many:
di- for two groups,
tri- for three groups, tetra- for four groups, and so
forth. The following compound has two methyl groups
so its name contains
the prefix di- before methyl → di
methyl.
7 6 5 4 3 2 1
CH3 - CH2 - CH2 –CH–CH–CH-CH3
CH2 CH3 CH3
CH3
• Step 4: Use prefixes to indicate the appeara
nce of a group more than once in the
structure.
Di = twice
Tri = three times
Tetra = four times
Penta = five times
7 6 5 4 3 2 1
CH3- CH2- CH2– CH – CH – CH - CH3
CH2 CH3 CH3
CH3
• This chain has 2 methyl groups
so dimethyl is used.

Step 5: List the alkyl groups

in alphabetical order.
In this ex. dimethyl is listed
before the ethyl.
7 6 5 4 3 2 1
CH3- CH2- CH2– CH – CH – CH - CH3
CH2 CH3 CH3 CH3

Step 6: Use punctuation

- use commas to
separate numbers
-hyphens to separate
numbers with words.
7 6 5 4 3 2 1
CH3- CH2- CH2– CH – CH – CH - CH3
CH2 CH3 CH3
CH3
• The name of this compound is:

2,3-dimethyl – 4-ethyl
heptane
 CH3 CH3
CH3 - CH2 –CH–CH2 –CH-CH3
6 5 4 3 2 1

Step 1: 6 carbons = hex

All single bonds = ends in ane
So parent chain is hexane
Step 2: start numbering from right to left

Step 3: 2 -methyl and 4-methyl

 CH3 CH3
CH3 - CH2 –CH–CH2 –CH-CH3
6 5 4 3 2 1

2,4 dimethyl hexane

Now start with name and draw the
structure 3.-ethylhexane

yl
ethane
C2H6
5
H
 Now start with name and draw the
structure 3.-ethylhexane

C C C C C C
CH2
CH3
You can place H’s all around or just leave as is.

H C H
yl
H C H ethane
C2H6
 5
H
• 2,2,4-trimethylpentane

CH3
C C C C C
CH3 CH3
When naming with a double/triple bond- start # car
closest to the bond.

CH3 CH3
C C C C C
1 2 3 4 5

3,4 dimethyl, 2-pentene

NOMENCLATURE FOR
ALKANES (LET’S HAVE
ANOTHER APPROACH)
Rule 1: Identify the longest
continuous carbon chain (the
parent chain), which may or may
not be shown in a straight line, and
name the chain.
Rule 2: Number the carbon atoms
in the parent chain from the end of
the chain nearest a substituent
(alkyl group).

There always are two ways to number the chain (either from left
to right or from right to left). This rule gives the first-encountered
alkyl group the lowest possible number
Rule 3: If only one alkyl group is
present, name and locate it (by
number), and prefix the number
and name to that of the parent
carbon chain.
Rule 4: If two or more of the same
kind of alkyl group are present in a
molecule, indicate the number with a
Greek numerical prefix (di-, tri-,
tetra-, penta-, and so forth).

In addition, a number specifying the location of each identical

group must be included. These position numbers, separated by
commas, precede the numerical prefix. Numbers are separated
from words by hyphens.
Rule 5: When two kinds of alkyl
groups are present on the same
carbon chain, number each
group separately, and list the
names of the alkyl groups in
alphabetical order.
Note that ethyl is named first in
accordance with the alphabetical rule.
Note that the prefix di- does not affect
the alphabetical order; ethyl precedes
propyl.
Rule 6: Follow IUPAC punctuation rules,
which include the following:
(1) Separate numbers from each other by
commas.
(2) Separate numbers from letters by
hyphens.
(3) Do not add a hyphen or a space between
the last-named substituent and the name of
the parent alkane that follows.
Draw the condensed
structural formula for 3-ethyl-
2,3 dimethylpentane.

Draw the condensed

structural formula for 4,5-
diethyl-3,4,5-trimethyloctane.
II. Nomenclature of
CYCLOALKANES
II. Nomenclature of CYCLOALKANES
1. If there is just one ring substituent, it is
not necessary to locate it by number.
2. When two ring substituents are present, the
carbon atoms in the ring are numbered
beginning with the substituent of higher
alphabetical priority and proceeding in the
direction (clockwise or counterclockwise) that
gives the other substituent the lower number.
3. When three or more ring substituents are
present, ring numbering begins at the
substituent that leads to the lowest set of
location numbers. When two or more equivalent
numbering sets exist, alphabetical priority
among substituents determines the set used.
III. Nomenclature of
ALKENES AND
CYCLOALKENES
III. Nomenclature of
ALKENES AND CYCLOALKENES
Rule 1. Replace the alkane suffix -ane with the suffix -ene,
which is used to indicate the presence of a carbon–carbon
double bond.

Rule 2. Select as the parent carbon chain the longest

continuous chain of carbon atoms that contains both carbon
atoms of the double bond. For example, select
III. Nomenclature of
ALKENES AND CYCLOALKENES
Rule 3. Number the parent carbon chain beginning at the
end nearest the double bond.

If the double bond is equidistant from both ends of the parent

chain, begin numbering from the end closer to a substituent.

Rule 4. Give the position of the double bond in the chain as a single
number, which is the lower-numbered carbon atom participating in
the double bond. This number is placed immediately before
the name of the parent carbon chain
Rule 5. Use the suffixes -diene, -triene, -tetrene, and so on when
more than one double bond is present in the molecule. A separate
number must be used to locate each double bond.

Rule 6. A number is not needed to locate the double bond in

unsubstituted cycloalkenes with only one double bond because
that bond is assumed to be between carbons 1 and 2.
Rule 7. In substituted cycloalkenes with only one double bond,
the double-bonded carbon atoms are numbered 1 and 2 in the
direction (clockwise or counterclockwise) that gives the fi rst-
encountered substituent the lower number. Again, no number
is used in the name to locate the double bond.

Rule 8. In cycloalkenes with more than one double bond within the
ring, assign one double bond the numbers 1 and 2 and the
other double bonds the lowest numbers possible.
IV. Nomenclature of
ALKYNES
IV. Nomenclature of ALKYNES
The rules for naming alkynes are identical to those used to
name alkenes except the ending -yne is used instead of -ene.
Consider the following structures and their IUPAC names.
V. Nomenclature of
AROMATIC
HYDROCARBON
S
V. Nomenclature of AROMATIC HYDROCARBONS
Names for Aromatic Hydrocarbons
Replacement of one or more of the hydrogen atoms on benzene
with other groups produces benzene derivatives.
Benzene Derivatives with One Substituent
The IUPAC system of naming monosubstituted benzene derivatives
uses the name of the substituent as a prefix to the name benzene.
Examples of this type of nomenclature include:
Benzene Derivatives with Two Substituents
When two substituents, either the same or different, are attached
to a benzene ring, three isomeric structures are possible.

When numbers are used, the three isomeric dichlorobenzenes

have the first listed set of names:
When one of the two substituents in a disubstituted benzene imparts
a special name to the compound (as, for example, toluene), the
compound is named as a derivative of that parent molecule. The
special substituent is assumed to be at ring position 1.
When neither substituent group imparts a special name, the
substituents are cited in alphabetical order before the ending -
benzene. The carbon of the benzene ring bearing the
substituent with alphabetical priority becomes carbon 1.
Benzene Derivatives with Three or More Substituents
When more than two groups are present on the benzene ring, their
positions are indicated with numbers. The ring is numbered in such
a way as to obtain the lowest possible numbers for the carbon atoms
that have substituents. If there is a choice of numbering systems
(two systems give the same lowest set), then the group that comes
first alphabetically is given the lower number.
END of LECTURE 10