Naming Branched-Chain Alkanes

Key Concepts
Naming Branched-Chain Alkanes:

Name of a branched-chain alkane is made up of two parts:

alkyl alkane
branch name stem name
prefix suffix

Name the longest alkane carbon chain (stem) first.

Identify the branches (side chains).

Name each branch (side chain).

Name
Number of carbon atoms in branch (side chain) Structure
(alkyl)
-stem-
|
1 H-C-H methyl
|
H

-stem-
|
H-C-H
2 | ethyl
H-C-H
|
H
 -stem-
|
H-C-H
|
3 H-C-H propyl
|
H-C-H
|
H

Number the carbon atoms making up the stem so that the branches have the lowest possible
numbers.

Separate the number of the stem carbon atom from the name of the branch by a hyphen (-).

If two or more identical branches are present:

(i) Use the prefixes di, tri, tetra, etc before the branch name.

number of identical branches prefix

2 di
3 tri
4 tetra

(ii) Indicate the location of the stem carbon atoms to which each branch is attached by
writing the numbers separated by a comma (,) in ascending order.
(iii) Separate the final number from the prefix of the branch name by a hyphen (-).

If two or more different branches (side chains) are present:

(i) Identify and name each branch (side chain).
(ii) Indicate the location of the stem carbon atoms to which each branch is attached by
writing the number then a hyphen and then the name of the branch.
(ii) Write the names of the branches in alphabetical order (ignoring any di, tri, tetra, etc
prefix) separating numbers from letters by a hyphen.

Branch name(s) added as a prefix to the name of the stem.

Drawing the structure1 of branched-chain alkanes:

Divide the name into the name of the branches and the name of the stem.

Draw the straight chain alkane stem.

 Number the carbon atoms making up the stem's chain.

Break the rest of the name up into individual branch names.

Determine the number of identical branches (if any).

Determine the location of the carbon atom on the stem to which each branch (side chain) is
attached.

Note the locations of the branches on the numbered stem chain you have already drawn.

Draw the required number of carbon atoms for each branch at the specified location along
the stem's carbon chain.

Complete the structure by adding a hydrogen atom at the end of any vacant covalent bond.

Molecular formula of branched-chain alkanes:2

Draw the structure of the branched-chain alkane.

Write a skeletal molecular formula using the symbols for carbon and hydrogen:

C H

Count the number of carbon atoms in total in the structure.

total number of carbon atoms = n

Write the number of carbon atoms as a subscript number to the right of the symbol for
carbon

CnH

Count the number of hydrogen atoms in total in the structure.

total number of hydrogen atoms = y

Write the number of hydrogen atoms as a subscript number to the right of the symbol for
carbon

CnHy
 The general molecular formula for a branched-chain alkane is CnH2n+2

where n = number of carbon atoms in the carbon chain

Examples: Naming a Branched-Chain Alkane

Name the molecule shown below:
H H
| |
H H H-C-H H-C-H H H
| | | | | |
H- C - C - C - C - C - C -H
| | | | | |
H H H-C-H H H H
|
H-C-H
|
H

Step 1. Name the longest alkane carbon chain (stem) first.

H H
| |
H H H-C-H H-C-H H H
| | | | | |
H- C - C - C - C - C - C -H
| | | | | |
H H H-C-H H H H
|
H-C-H
|
H

6 carbon atoms in the longest carbon chain.

6 carbon atoms prefix = hex

Only single bonds between carbon atoms in the chain

suffix = ane

Name of longest alkane carbon chain, stem, is hexane

Step 2. Identify the branches (side chains).

H H
| |
H H H-C-H H-C-H H H
| | | | | |
H- C - C - C - C - C - C -H
| | | | | |
H H H-C-H H H H
|
H-C-H
|
H

Step 3. Name each branch (side chain).

H H
methyl methyl
| |
H H H-C-H H-C-H H H
| | | | | |
H- C - C - C - C - C - C -H
| | | | | |
H H H-C-H H H H
|
H-C-H
|
ethyl
H

Step 4. Number the carbon atoms making up the stem so that the branches have the lowest
possible numbers.

H H
methyl methyl
| |
H H H-C-H H-C-H H H
| | | | | |
H- C - C2 -
1
C3 - C4 - C - C6
5
-H
| | | | | |
H H H-C-H H H H
|
H-C-H
|
ethyl
H
Step 5. Separate the number of the stem carbon atom from the name of the branch by a hyphen
(-).

H H
3-methyl 4-methyl
| |
H H H-C-H H-C-H H H
| | | | | |
H- C1 - C2 - C3 - C4 - C5 - C6 -H
| | | | | |
H H H-C-H H H H
|
H-C-H
|
3-ethyl
H

Step 6 (a) Branch name(s) added as a prefix to the name of the stem.

More than 1 branch is present, go to step 6 (b)

Step 6 (b) If two or more identical branches are present:

(i) Use the prefixes di, tri, tetra, etc before the branch name.

Two methyl branches

dimethyl

(ii) Indicate the location of the stem carbon atoms to which each branch is attached by writing
the numbers in ascending order separated by a comma (,).
3,4

(iii) Separate the final number from the prefix of the branch name by a hyphen (-).
3,4-dimethyl

Step 6 (c) If two or more different branches (side chains) are present:
(i) Identify and name each branch (side chain).

1 x ethyl
2 x methyl named above as 3,4-dimethyl

(ii) Indicate the location of the stem carbon atoms to which each branch is attached by writing
the number then a hyphen and then the name of the branch.
3-ethyl
3,4-dimethyl

(ii) Write the names of the branches in alphabetical order (ignoring any di, tri, tetra, etc prefix)
separating numbers from letters by a hyphen.
3-ethyl-3,4-dimethyl
Write the complete name by adding the prefix (name of all the branches) to the suffix (name of
the stem alkane)

3-ethyl-3,4-dimethylhexane

Examples: Drawing the Structure of a Branched-Chain

Alkane
Draw the structure of 2,2-dimethylpropane.

Step 1: Divide the name of the branched-chain alkane into two parts:

general name: alkyl alkane

branch name stem name
prefix suffix
example 2,2-dimethyl propane

Step 2: Draw the straight chain alkane stem

stem = propane

prefix = number of carbon atoms in chain = 3 (prop)

suffix = type of bonds between carbon atoms in chain = single bonds (ane)

| | |
- C - C - C -
| | |

Note that each carbon atom can make 4 covalent bonds and that we are drawing in all 4 bonds,
even the ones that are not joining two carbon atoms together in the chain.

Step 3: Number the carbon atoms in the stem

| | |
- C1 - C2 - C3 -
| | |

Step 4: Break the the branch name up into individual branch (side chain) names:

2,2-dimethyl

Only one type of branch (side chain): methyl

 Methyl branches contain only 1 carbon atom.

Step 5: Determine the number of identical branches (side chains):

2,2-dimethyl

There are two methyl groups: di

Step 6: Determine the location of the carbon atom on the stem to which each branch (side chain)
is attached:

2,2-dimethyl

Both methyl branches are attached to carbon number 2 along the stem: 2,2-

Step 7: Identify the location of each branch along the stem:

| | |
- C1 - C2 - C3 -
| | |

Both methyl branches (side chains) will be attached to C2

Step 5: Draw in the required number of carbon atoms for each branch at the specified location
along the stem's carbon chain:

|
-C-
| | |
- C1 - C2 - C3 -
| | |
-C-
|

Notice that we are still drawing in all 4 covalent bonds for each carbon atom, even when the
bond is not between two carbon atoms.

Step 6: Complete the structure by placing a hydrogen atom (H) at the end of any vacant covalent
bond:

H
|
H-C-H
H H
|
| |
 H- C - C - C -H
| |
|
H H
H-C-H
|
H

Examples: Writing the Molecular Formula of Branched-

Chain Alkanes
Write the molecular formula for 2-methylpropane.

Step 1: Draw the structure of the branched alkane molecule.

H
|
H-C-H
H H
|
| |
H- C - C - C -H
| | |
H H H

Step 2: Write a skeleton molecular formula using the symbols for carbon (C) and hydrogen (H)

CH

Step 3: Count the total number of carbon atoms in the branched-chain alkane molecule.

H
|
H-C1-H
H H
|
| |
H- C2 - C3 - C4 -H
| | |
H H H

There are a total of 4 carbon atoms in the molecule.

Step 4: Write the number of of carbon atoms into the skeleton molecular formula as a subscript
number to the right of the symbol for carbon (C).

C4H
Step 5: Count the total number of hydrogen atoms in the branched-chain alkane molecule.

H4
|
H3-C-H5
H2 H6
|
| |
H1- C - C - C -H7
| | |
H10 H9 H8

There are a total of 10 hydrogen atoms in the molecule.

Step 6: Write the number of of hydrogen atoms into the skeleton molecular formula as a
subscript number to the right of the symbol for hydrogen (H).

C4H10

Step 7: Check that your completed molecular formula makes sense (CnH2n+2)

when n = 4
2n + 2 = (2 x 4) + 2 = 8 + 2 = 10
So, C4H10 is the molecular formula for the alkane
Introduction to the IUPAC System for Naming
Carbon Compounds

Key Concepts
Nomenclature is a system of rules by which the names of compounds are formed.

For nomenclature purposes, all compounds containing carbon are said to be organic
compounds.

When naming organic compounds, punctuation marks are used for specific purposes:1:

(i) the first letter of the name is not a capital letter unless the name occurs at the beginning
of a sentence
Example: Acetone is the preferred IUPAC name for propan-2-one.

(ii) commas (,) are used to separate one number from another number
Example: the numbers 1 and 2 are written as 1,2

(iii) hyphens (-) are used to separate a number from a letter

Example: 2-methylpropane and propan-2-ol

(iv) there are no spaces (gaps) between letters unless the compound is a

(a) carboxylic acid: a space between alkanoic and acid

Example: butanoic acid
 (b) salts: a space between the names of the cation and the anion
Example: sodium butanoate

(c) acid halides: a space between name derived from carboxylic acid (alkanoyl) and the
halogen (halide)
Example: butanoyl chloride

(d) ester : a space between name derived from alcohol (alkyl) and that derived from
alkanoic acid (alkanoate)
Example: ethyl butanoate

(e) acid anhydride: a space between alkanoic and anhydride

Example: acetic anhydride

Hydrocarbon molecules, those made up of only carbon and hydrogen atoms, are the basis
upon which the name of an organic molecule is constructed.

The name of the hydrocarbon used as the basis for the construction of the name of an
organic molecule is referred to as the parent hydrocarbon2.

The name of the parent hydrocarbon is made up of a prefix and a suffix:

parent hydrocarbon
prefix suffix

The principal nomenclature used in organic chemistry, and which forms the basis of most
IUPAC3 preferred names, is substitutive nomenclature.

Substitutive nomenclature is based on the concept of different atoms, or groups of atoms,

substituting for the atoms on a parent hydrocarbon molecule.
These atoms, or groups of atoms, are known as substituents.

The name of an organic compound containing a substituent is constructed by modifying the

name of the parent hydrocarbon using prefixes and suffixes:

organic compound name

prefix parent hydrocarbon suffix

Note that the prefixes and/or suffixes themselves may include infixes (numbers which tell
us the location of the substituent).
 For simple organic compounds containing only one type of functional group:

(i) Prefixes are modified by branches (side chains) and by the presence of halogens

(ii) Suffixes are modified by the presence of the functional groups OH, C=O, COOH, NH2

The construction of substitutive names using the parent hydrocarbon as a foundation

requires the application of 4 general rules:

1. numbering (of the longest carbon chain)

2. locants (location of structural features along the chain)

3. multiplying prefixes (di, tri, tetra etc)

4. alphanumerical order (ascending alphabetical order by first letter)

Important exceptions to the use of substitutive names as preferred IUPAC names

(i) anhydrides : functional class nomenclature is preferred

example: acetic anhydride is the preferred name for CH3-CO-O-CO-CH3

(ii) esters: functional class nomenclature is preferred

example: methyl propanoate is the preferred IUPAC name for CH3-CH2-CO-O-CH3

(iii) polymers : the name of the repeating unit can be based on either its source or its
structure

Note the preferred IUPAC spelling for the following elements:

(i) Name of the element with the symbol S is sulfur (not sulphur).
(ii) Name of the element with the symbol Al is aluminium (not aluminum).
(iii) Name of the element with the symbol Cs is caesium (not cesium).

Parent Hydrocarbon
The parent hydrocarbon can be

a chain of carbon atoms (called an acyclic aliphatic compound4 )

a ring of carbon atoms (called an alicyclic or aliphatic cyclic compound)

a benzene ring (called an aromatic compound5)

The prefix for the name of an aliphatic parent hydrocarbon is determined by the number of carbon
atoms in the chain or ring.
The prefix for the first four hydrocarbons in the series is based on a traditional name and the prefix
has been retained.
Prefixes for aliphatic parent hydrocarbons containing more than four carbon atoms are based on
multiplying prefixes (that is, the multiplying prefix with the final "a" removed, eg, penta becomes
pent).

Number of carbon
1 2 3 4 5 6 7 8 9 10
atoms:

met pro
Prefix: eth but pent hex hept oct non dec
h p

retained names multiplying prefix

The suffix of an aliphatic parent hydrocarbon is determined by the nature of the covalent bonding
between carbon atoms in the chain or the ring:

single covalent bonds : suffix ane (see naming straight-chain alkanes)

double bond(s) : suffix ene (see naming straight-chain alkenes)

triple bond(s) : suffix yne (see naming straight-chain alkynes)

When one double or triple bond is present, an infix is required to tell us the location of the double
or triple bond.
The infix is a number which is separated from the prefix and the suffix by a hyphen:

prefix-infix-suffix

If more than one double or triple bond is present in the parent hydrocarbon,
(i) an "a" may be added to the prefix of the parent hydrocarbon for euphonic reasons

buta, penta

(ii) a multiplying prefix (di, tri, tetra, etc) is also required and is added to the beginning of the
suffix, in addition to an infix to describe the loction of each double or triple bond:
prefix-infix-multiplyingsuffix

If both double and triple bonds are present in the parent hydrocabon, an enyne molecule, then the
en suffix is written before the yne suffix (that is, written in alphabetical order).
However, when numbering the carbon chain, the triple bond takes precedence over the double
bond, so the set of locants will be chosen to give the triple bond(s) the lowest number(s) in
preference to the double bond(s).

prefix-infix-multiplyingen-infix-multiplyingyne

If the aliphatic compound is a ring rather than a chain, cyclo is added to the beginning if the prefix:

cycloprefix-infix-multiplyingsuffix

Substituents
A substituent is an atom, or group of atoms, that substitutes for one or more hydrogen atoms on the
parent hydrocarbon.

A substituent can be an alkyl group, a halogen atom or other functional group.

Alkyl groups (unbranched acyclic alkane-based hydrocarbons attached to a parent

hydrocarbon)

Alkyl groups are hydrocarbons that are themselves attached to the parent hydrocarbon
molecule. The alkyl groups "branch off" the main "stem" of the parent, so these alkyl
groups are often referred to as branches (or alternatively as side-chains). The presence of
alkyl groups modifies the name of the parent hydrocarbon by adding a prefix to it.

The prefix attached to the name of the parent hydrocarbon to represent a branch or side-
chain ends in yl.

Alkyl groups can thought of a straight chain alkane in which a hydrogen atom (H.)6 has
been removed. This hydrogen atom can be removed from a terminal (end) carbon atom, or
from a non-terminal carbon atom.

(i) Removal of one hydrogen atom from a terminal (end) carbon atom of the alkane
Named by removing the "ane" from the alkane and replacing it with yl to make alkyl:

alkane alkyl group alkyl group

(Lewis Structure) (Lewis Structure) (Valence Structure)
H H H
.. .. |
H: C :H . C :H - C -H
remove H.
.. .. |
H H H
methane methyl methyl

(ii) Removal of one hydrogen atom form a non-terminal carbon atom of an alkane.
Named by dropping the final e of alkane then inserting an infix for the location of the
 missing hydrogen atom followed by a hyphen and the yl ending to make alkan-infix-yl:

alkane alkyl group alkyl group

(Lewis Structure) (Lewis Structure) (Valence Structure)
H H H H H H H H H H H H
.. .. .. .. .. .. .. .. | | | |
H: C : C : C : C :H H: C : C : C : C :H H- C - C - C - C -H
remove H.
.. .. .. .. .. .. . .. | | | |
H H H H H H H H H H
butane butan-2-yl butan-2-yl

Alkyl groups are written in ascending alphabetical order, using an infix to identify the
location of each alkyl group, and a muliplying prefix if there is more than one of each type
of alkyl group:

example: infix-multiplyingethyl-infix-multiplyingmethyl-infix-multiplyingpropyl

and all of this is added as a prefix to the name of the parent hydrocarbon.

Halogen atoms as substituents.

A halogen atom (fluorine, chlorine, bromine or iodine atom) can replace any or all of the
hydrogen atoms on a parent hydrocarbon molecule.
When naming an organic molecule containing halogen substituents, the halogen is named
by dropping the "ine" ending on the name of the element and adding "o" as an ending.

Symbol for halogen F Cl Br I

Name of Element fluorine chlorine bromine iodine
Prefix Used in Nomenclature fluoro chloro bromo iodo

These "halo" names are written in alphabetical order, preceded by an infix to identify the
location of each halogen atom along the chain, as well as a multiplying prefix if more than
one type of halogen is present:

infix-multiplyingbromo-infix-multiplyingchloro-infix-multiplyingfluoro-infix-
multiplyingiodo

and all of this is then added as a prefix to the name of the parent hydrocarbon.
Note that if the compound contains both alkyl substituents and halogen substituents, then
the names of all these substituents are placed in alphabetical order
 Example: infix-multiplyingbromo-infix-multiplyingchloro-infix-multiplyingethyl-infix-multiplyingflouro-infix-multiplyingmethyl

Functional (or characteristic) groups as substituents

An organic molecule may contain:

(i) only one type of functional group
(ii) more than one type of functional group

(i) Organic molecules in which only one type of functional group is present.

When only one type of functional group is present in an organic molecule, then the
functional group modifies the suffix attached to the name of the parent hydrocarbon:

parent hydrocarbon functional group suffix

alkan suffix

The functional groups you are most likely to meet during an introductory chemistry course
are:

type formula nomenclature

carboxylic acids COOH (terminal C atom) oic acid (suffix) (see naming alkanoic acids)

(functional naming rather than substitutive naming is preferred)

esters -CO-O-C (see esters and esterification)

aldehydes C=O (terminal C atom) al (suffix) (see naming alkanals)

ketones C=O (non-terminal C atom) one (suffix) (see naming alkanones)

alcohols OH ol (suffix) (see naming straight-chain alkanols)

amines NH2 amine (suffix) (see naming amines)

amides CO-NH2 amide (suffix) (see naming amides)

Notice that these functional groups will modify the suffix of the parent hydrocarbon as
shown in the table above.
If only one type of functional group is present in the organic molecule, an infix is not
required when naming carboxylic acids or aldehydes as the functional group will also be
defined as attached to the first carbon atom in the chain or ring.
If only one type of functional group is present, but only one atom of carbon is present in the
parent hydrocarbon, no infix is required since the functional group can only be attached to
 the first carbon atom by definition. Similarly, if the molecule contains 2 carbon atoms
which are otherwise identical except that one is attached to the functional group, then the
infix may not be required.

When the suffix is added directly to the name of the parent hydrocarbon, the name of the
parent hydrocarbon may be changed by removal of the final "e" from a parent alkane,
alkene or alkyne, if the suffix to be added begins with a vowel or the letter "y"
Example: ethanol not ethaneol but, ethane-1,2-diol is preferred to ethan-1,2-diol

(ii) The construction of the name of an organic molecule that includes more than one
functional (characteristic) group relies on the principle of seniority of classes.
The order of seniority is used to choose a parent hydrocarbon.
The senior parent structure has the maximum number of substituents corresponding to the
principal characteristic (functional) group in accord with the seniority of classes and
suffixes shown in the table below:

seniority compound class

1 Radicals
2 Radical anions
3 Radical cations
4 Anions
5 Zwitterions
6 Cations
7 Acids
8 Anhydrides
9 Esters
10 Acid halides and pseudohalides
11 Amides
12 Hydrazides
13 Imides
14 Nitriles
15 Aldehydes and chalcogen analogues
16 Ketones, pseudoketones and heterones.
17 Hydroxy compounds and chalcogen analogues
18 Hydroperoxides (peroxols)
19 Amines
20 Imines

Within the same class, the preferred IUPAC nomenclature gives seniority to a ring over a
chain.
 The most senior class is used to construct the suffix for the parent hydrocarbon.
Other less senior functional groups are then used to construct modifying prefixes (including
infixes and multiplying prefixes) to add to the name of the parent hydrocarbon.

Construction of Substitutive Names: Numbering Rule

(i) If only one structural feature is present, the longest carbon chain is numbered so that the locant
is assigned the lowest possible number.
This locant is cited as an infix, that is, placed immediately in front of the feature being named.

(ii) If more than one structural feature is present, the longest carbon chain is numbered so that
locants are assigned to each structural feature in order of decreasing seniority.

For simple organic molecules you are likely to encounter in an introductory chemistry course, the
lowest locants are assigned in the following order:

1st characteristic (functional) group cited as the suffix

2nd unsaturation (double bond "ene" or triple bond "yne")

3rd detachable alphabetized prefixes (alkyl groups)

Example,

numbering from left to right or numbering from right to left

H H H OH H CH3 H H H H OH H CH3 H
| | | | | | | | | | | | | |
H- C1 - C2 = C3 - C4 - C5 - C6 - C7 -H H- C7 - C6 = C5 - C4 - C3 - C2 - C1 -H
| | | | | | | | | |
H H H H H H H H H H
st st
1 : characteristic group cited as suffix: 1 : characteristic group cited as suffix:
OH locant is 4 OH locant is 4
2nd: unsaturation: double bond locant is 2 2nd: unsaturation: double bond locant is 5
3rd: detachable alphabetized prefixes: 3rd: detachable alphabetized prefixes:
methyl locant is 6 methyl locant is 2

Since both numbering methods result in the OH group having a locant of 4, we move on to
compare the locants for the double bond.
Numbering from left to right results in the lowest locant for the double bond, so the preferred
numbering is from left to right.
The name of the molecule is therefore 6-methylhept-2-en-4-ol

Construction of Substitutive Names: Locant Rule

Locants are arabic numbers (1, 2, 3 etc) indicating the location of a structural feature, such as a
functional group, alkyl group or unsaturation (double or triple bond), on a parent hydrocarbon.
Numbers are assigned to carbon atoms in a chain in ascending order as described above in the
section "Numbering".

H Cl CH3 H H
| | | | | Locant for the hydroxy (hydroxyl) group, is 1
H- C - C - C - C - C1 -OH
5 4 3 2
Locant for the methyl group, is 3
| | | | | Locant for the chlorine atom, is 4
H H H H H

Locants are placed immediately before that part of the name to which they relate, forming the basis
of the infix of a name7.
Example:

1-ol
3-methyl
4-chloro

If more than one of the same structural feature is present, then a locant must be included for each
and every feature.
For multiple instances of structural features with the same seniority, the lowest set of locants is
used.
The lowest set of locants is defined as the set that, when compared term by term with other locant
sets, each cited in order of increasing value, has the lowest term at the point of difference.

Example:

H CH3 CH3 H H H CH3 CH3 H H

| | | | | | | | | |
H- C1 - C2 - C3 - C4 - C5 -H H- C5 - C4 - C3 - C2 - C1 -H
| | | | | | | | | |
H H H H H H H H H H
Numbering from left to right produces Numbering from right to left produces
the locant set 2,3 for the methyl groups the locant set 3,4 for the methyl groups
Compare the two sets side by side
first term in second term in
set set
first set Point of difference occurs at the beginning of the
(left to 2 3 sets.
right) 2 (first set) is less than 3 (second set)
second set
(right to 3 4 first set of locants is preferred
left)
Locants should always be included in the IUPAC name unless:

the compound is an alkanoic acid or alkanedioc acid

example: CH3-CH2-CH2-COOH is named as butanoic acid (not butan-1-oic acid)
example: HOOC-CH2-CH2-COOH is named as butanedioc acid (not as butane-1,4-dioic
acid)

the compound is an alkanal

example: CH3-CH2-CHO is propanal (not propan-1-al)

the compound contains only one carbon atom

example: CH3Cl is chloromethane (not 1-chloromethane)

the compound contains only two carbon atoms and only one functional group is present
example: CH3-CH2-OH is named ethanol (not ethan-1-ol)

the compound results from the single substitution of a hydrogen atom on a benzene ring or
cyclic alkane

example: H Br named as bromobenzene (not 1-bromobenzene)

all substitutable positions are completely substituted

example: CF3-CF2-CF2-COOH is named heptafluorobutanoic acid (not 2,2,3,3,4,4,4-
heptafluorobutanoic acid)

Construction of Substitutive Names: Multiplying Prefixes

When more than one instance of the same structural feature is present in a molecule, a multiplying
prefix is used which tells us how many there are.
multiplying Prefixes
numbe
(1) 2 3 4 5 6 7 8 9 10
r
prefix (hen) di tri tetra penta hexa hepta octa nona deca

numbe
11 20 30 40 50 60 70 80 90 100
r
triacont tetracont pentacont hexacont heptacont octacont nonacont
prefix hendeca icosa hecta
a a a a a a a

numbe
101 200 300 400 500 600 700 800 900 1000
r
henhect
prefix dicta tricta tetracta pentacta hexacta heptacta octacta nonacta kilia
a
numbe
1001 2000 3000 4000 5000 6000 7000 8000 9000
r
prefix henkilia dilia trilia tetralia pentalia hexalia heptalia octalia nonalia

There must be as many numbers representing the locants of each feature as are indicated by the
multiplying prefix.
Example: the infix 1,1- requires the multiplying prefix di because there are two numbers
Example: the infix 2,2,3,5- requires the multiplying prefix tetra because there are four numbers

Example: 2,2-dimethylbutane tells us there are two methyl groups (dimethyl) and that both methyl
groups are attached to the second carbon atom (2,2-) in the chain.

Note that a multiplying prefix is not required if there is only one instance of a particular structural
feature
Example: 2-chlorobutane (not 2-chlorohenbutane and not 2-chloromonobutane)

Construction of Substitutive Names: Alphanumerical Order

Simple prefixes, that is, prefixes describing atoms and unsubstituted substituents, are arranged
alphabetically.

For the substituents you are likely to meet during your introductory chemistry course, the order of
citation will be:

order of citation first second third fourth fith sixth seventh

substituent bromo chloro ethyl fluoro iodio methyl propyl

The addition of a multiplying prefix (di, tri, tetra etc) to the beginning of the name of the
substituent does NOT change the order of citation:
example: tetrabromo would still be cited before dichloro

1
Parenthese (), brackets [] and braces {} are also used when naming oganic molecules.
While you will probably not be needing these in an introductory chemistry course, you might need them when writing a linear (condensed
structural) formula :
(i) parentheses (round brackets) used when a functional group is attached to part of a chain
example: CH3-CH(OH)-CO-CH3 is the linear formula for 3-hydroxybutan-2-one.
(ii) brackets [square brackets] used when a group is repeated in a chain
example: CH3-[CH2]68-CH3 is the linear formula for heptacontane

2
More correctly we should refer to the parent hydride rather than the parent hydrocarbon since other atoms can substitute for carbon within the
parent structure.

3
IUPAC is the abbreviation for the International Union of Pure and Applied Chemistry.
IUPAC nomenclature began in 1892 when an international assembly of Chemists met in Geneva, Switzerland, to try to come up with a rational
system for naming organic molecules.
The rules for naming organic compounds are still being developed.
The most recent document for referral is "Preferred names in the nomenclature of organic compounds" (Draft 7 October 2004).
This document supercedes 'Nomenclature of Organic Chemistry, 1979 Edition' and 'A Guide to IUPAC Nomenclature of Organic Compounds,
Recommendations 1993'.
The current document recognises that there is more than one way to systematically name organic compounds, and develops rules for assigning
"preferred IUPAC names", but any other name, as long as it is unambiguous and follows the principles of the IUPAC recommendations is
acceptable as a "general IUPAC name".
As a result, there are examples of "preferred IUPAC" names that are based on the tradition of use, rather than a system of naming. Examples of
these traditional names that students may be expected to know are acetone, acetic acid and its derivatives such as ethyl acetate and acetic
anhydride, formic acid and its derivatives such as ethyl formate.

4
The term aliphatic comes from the Greek aleiphatos meaning "fat". Early Chemists did not know the structure of a fat, but they did know that
compounds containing long hydrocarbon chains behaved in a similar way to fats. So compounds containing hydrocarbon chains came to be
known as aliphatic compounds.

5
Benzene is a member of a class of compounds known as aromatic compounds. It was noted that many compounds containing benzene had a
distinctive odour or aroma, so historically they came to be known as aromatic compounds.

6
Note that this is a hydrogen atom, that is the nucleus of the hydrogen atom as well as its valence electron, also known as monohydrogen
Removal of the hydrogen atom's valence electron would produce a positively charged hydrogen ion, H +, known as a hydron (or a proton if the
original hydrogen atom was 1H)
Addition of an electron to the hydrogen atom would produce a negatively charged hydrogen ion, H-, known as hydride ("ide" indicating a
negatively charged ion)

7
Except in the case of the traditional contracted names when locants are added at the front of the name.
Naming Straight-Chain Alkenes

Key Concepts
Alkenes are hydrocarbons in which there is a double bond between two carbon atoms1:

C=C

The systematic IUPAC2 name of all simple straight-chain alkenes ends in "ene".

The systematic IUPAC name of a straight-chain alk-n-ene is made up of three parts3:

(i) A prefix which tells us how many carbon atoms are in the chain (alk).

No. carbon atoms 1 2 3 4 5 6 7 8 9 10

Prefix meth eth prop but pent hex hept oct non dec

(ii) An infix which is a number that tells us the location of the double bond (-n-)

(ii) The suffix ene telling us that a double bond is present within the chain.

Note that the preferred IUPAC name4 may not be the same as the systematic IUPAC name:

The preferred IUPAC name for the compound H2C=CH2 is ethylene rather than the
systematic IUPAC name ethene.

Naming Straight-Chain Alkenes:

Identify the longest carbon chain containing the double bond.

Determine the prefix for the name of the alkene based on the number of carbon atoms in the
chain.

Number each carbon atom along the longest carbon chain so that the double bonded carbon
atoms have the lowest possible number.

Determine the infix for the name of the alkene based on the location of the double bond
 (use the lowest number out of the two carbon atoms joined by the double bond).

Note that the infix may not be required if the longest carbon chain contains only two or
three carbon atoms.

Determine the suffix for the name of the alkene. All straight chain alkenes containing one
double bond will end in "ene".

Write the name for the alkene in the form of prefix-infix-suffix

Example

Give the systematic IUPAC name for this alkene:

H H H H
| | | |
H- C - C = C - C -H
| |
H H

Identify the longest carbon chain containing the double bond.

H H H H
| | | |
H- C - C = C - C -H
| |
H H

Determine the prefix for the name of the alkene based on the number of carbon atoms in the
chain.

Longest carbon chain contains four carbon atoms.

prefix is but

Number each carbon atom along the longest carbon chain so that the double bonded carbon
atoms have the lowest possible number.

numbering from left to right numbering from right to left

H H H H H H H H
| | | | | | | |
H- C1 - C2 = C3 - C4 -H OR H- C4 - C3 = C2 - C1 -H
| | | |
H H H H
location of double bond: C2 location of double bond: C2

In this case the double bond occurs between C2 and C3 in both cases.

Determine the infix for the name of the alkene based on the location of the double bond
(use the lowest number out of the two carbon atoms joined by the double bond).

H H H H
| | | |
H- C - C2 = C - C -H
| |
H H

infix is -2-

Determine the suffix for the name of the alkene.

All straight chain alkenes containing one double bond will end in "ene".

Suffix is ene

Write the systematic IUPAC name for the alkene in the form of prefix-infix-suffix

Systematic IUPAC name is but-2-ene

Another systematic name is 2-butene

Drawing the structure5 of straight-chain alkenes:

Break the systematic IUPAC name of the alkene into its three parts:

alk -n- ene

prefix infix suffix

Determine the number of carbon atoms in the longest carbon chain using the prefix.

Draw a chain of carbon atoms of the required length using dashes to represent a single
covalent bond between each pair of carbon atoms.

Number the carbon atoms in the chain from left to right.

Determine the location of the double bond using the infix.

We know there is a double bond because the molecule's name has the suffix ene.
 Draw a second dash, a second covalent bond, between the carbon with the same number as
the infix, and the carbon atom with a number equal to the infix + 1 (that is, the adjacent
carbon atom on the right hand side if you have numbered your carbon chain from left to
right).

Draw dashes around each carbon atom in the chain such that each carbon atom makes 4
bonds.
Note that the carbon atoms involved in the double bond have already used 2 out of the 4
possible bonds in making the double bond!

Complete the structure by placing a hydrogen atom (H) at the end of all the vacant dashes.

Example:

Draw the structure for the molecule with the systematic IUPAC name of hex-2-ene.

Break the systematic IUPAC name of the alkene into its three parts:

hex -2- ene

prefix infix suffix

Determine the number of carbon atoms in the longest carbon chain using the prefix.

Prefix is hex so there are 6 carbon atoms in the longest carbon chain.

Draw a chain of carbon atoms of the required length using dashes to represent a single
covalent bond between each pair of carbon atoms.

C - C - C - C - C - C

Number the carbon atoms in the chain from left to right.

C1 - C2 - C3 - C4 - C5 - C6

Determine the location of the double bond using the infix.

We know there is a double bond because the molecule's name has the suffix ene.

Infix is 2, so this is the location of the double bond.

C - C2 - C - C - C - C

Draw a second dash, a second covalent bond, between the carbon with the same number as
the infix, and the carbon atom with a number equal to the infix + 1 (that is, the adjacent
 carbon atom on the right hand side if you have numbered your carbon chain from left to
right).

The double bond will occur between C2 and C3 (C2+1=3).

C - C2 = C3 - C - C - C

Draw dashes around each carbon atom in the chain such that each carbon atom makes 4
bonds.
Note that the carbon atoms involved in the double bond have already used 2 out of the 4
possible bonds in making the double bond!

| | | | | |
- C - C = C - C - C - C -
| | | |

Complete the structure by placing a hydrogen atom (H) at the end of all the vacant dashes.

H H H H H H
| | | | | |
H- C - C = C - C - C - C -H
| | | |
H H H H

Molecular formula of straight-chain alkenes:6

Draw the structure of the straight-chain alkene.

Write a skeletal molecular formula using the symbols for carbon and hydrogen:

C H

Count the number of carbon atoms in total in the structure.

total number of carbon atoms = n

Write the number of carbon atoms as a subscript number to the right of the symbol for
carbon

CnH

Count the number of hydrogen atoms in total in the structure.

 total number of hydrogen atoms = y

Write the number of hydrogen atoms as a subscript number to the right of the symbol for
carbon

CnHy

The general molecular formula for a straight-chain alkene is CnH2n

where n = number of carbon atoms in the carbon chain

Example:

Write the molecular formula for the molecule with the systematic IUPAC name of but-1-ene.

Draw the structure of the straight-chain alkene.

H H H H
| | | |
H- C = C - C - C -H
| |
H H

Write a skeletal molecular formula using the symbols for carbon and hydrogen:

C H

Count the number of carbon atoms in total in the structure.

H H H H
| | | |
H- C1 = C2 - C3 - C4 -H
| |
H H

total number of carbon atoms = n = 4

Write the number of carbon atoms as a subscript number to the right of the symbol for
carbon
 C4H

Count the number of hydrogen atoms in total in the structure.

H2 H3 H4 H5
| | | |
H1- C = C - C - C -H6
| |
H8 H7

total number of hydrogen atoms = y = 8

Write the number of hydrogen atoms as a subscript number to the right of the symbol for
carbon

C4H8

The general molecular formula for a straight-chain alkene is CnH2n

where n = number of carbon atoms in the carbon chain

When n = 4 = number of carbon atoms in alkene, then, the number of hydrogen atoms in
the alkene will equal 2 x 4 = 8

Summary Table for the Nomenclature of Simple Straight-

Chain Alkenes
no. C
Systematic IUPAC Molecular
atoms Other Names Structure
Name Formula
(n)
H H
ethylene | |
2 ethene (preferred IUPAC C2H4 C = C
| |
name) H H

H H
1-propene | |
3 prop-1-ene propene C3H6 C = C - C -H
| | |
propylene H H H

4 but-1-ene 1-butene C4H8 H H H

| | |
 C = C - C - C -H
| | | |
H H H H
H H H H
| | | |
but-2-ene 2-butene C4H8 H- C - C = C - C -H
| |
H H

H H H H
| | | |
pent-1-ene 1-pentene C5H10 C = C - C - C - C -H
| | | | |
H H H H H
5 H H H H H
| | | | |
pent-2-ene 2-pentene C5H10 H- C - C = C - C - C -H
| | |
H H H

H H H H H
| | | | |
hex-1-ene 1-hexene C6H12 C = C - C - C - C - C -H
| | | | | |
H H H H H H
H H H H H H
| | | | | |
6 hex-2-ene 2-hexene C6H12 H- C - C = C - C - C - C -H
| | | |
H H H H
H H H H H H
| | | | | |
hex-3-ene 3-hexene C6H12 H- C - C - C = C - C - C -H
| | | |
H H H H

H H H H H H
| | | | | |
hept-1-ene 1-heptene C7H14 C = C - C - C - C - C - C -H
| | | | | | |
H H H H H H H
H H H H H H H
| | | | | | |
7 hept-2-ene 2-heptene C7H14 H- C - C = C - C - C - C - C -H
| | | | |
H H H H H
H H H H H H H
| | | | | | |
hept-3-ene 3-heptene C7H14 H- C - C - C = C - C - C - C -H
| | | | |
H H H H H

8 H H H H H H H
| | | | | | |
oct-1-ene 1-octene C8H16 C = C - C - C - C - C - C - C -H
| | | | | | | |
H H H H H H H H
oct-2-ene 2-octene C8H16 H H H H H H H H
| | | | | | | |
H- C - C = C - C - C - C - C - C -H
 | | | | | |
H H H H H H
H H H H H H H H
| | | | | | | |
oct-3-ene 3-octene C8H16 H- C - C - C = C - C - C - C - C -H
| | | | | |
H H H H H H
H H H H H H H H
| | | | | | | |
oct-4-ene 4-octene C8H16 H- C - C - C - C = C - C - C - C -H
| | | | | |
H H H H H H