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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 IUPAC3preferred 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:

prefix

organic compound name


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:
a. numbering (of the longest carbon chain)
b. locants (location of structural features along the chain)
c. multiplying prefixes (di, tri, tetra etc)
d. 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 atoms:

10

Prefix:

meth

eth

prop

but

pent

hex

hept

oct

non

dec

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)

Key Concepts

Alkanes are hydrocarbons


(compounds containing ONLY carbon and hydrogen)

A single covalent bond joins one carbon atom in the chain to another carbon
atom.

The name of an alkane is made up of two parts:

(i) a prefix or stem (first part of the name, alk)


(ii) a suffix (last part of the name, ane)

The suffix when naming an alkane is always "ane"

The prefix or stem is dependent on the number of carbon atoms in the chain
of carbon atoms:

Number of
carbon atoms:

10

Prefix:

meth

eth

prop

but

pent

hex

hept

oct

non

dec

The general molecular formula for a straight chain alkane is C nH2n+2

where n = number of carbon atoms in the carbon chain


Bonding Concepts

Alkanes are hydrocarbons, that is, alkanes are compounds containing ONLY carbon
and hydrogen atoms.

Each carbon atom in the alkane molecule has 4 valence electrons.


.

Each hydrogen atom in the alkane molecule has 1 valence electron.

Each carbon atom in the alkane molecule makes 4 covalent bonds by sharing
a valence electron with another atom to make an octet of electrons (4
electron pairs).
Lewis Structure
(electron dot diagram)
.

Valence Structure

|
.

.
.

Each carbon atom can covalently bond to hydrogen atoms and to other
carbon atoms:
C-C

Lewis Structure

.
C
.

.
.

.
C
.

.
C
.

.
.

Valence Structure

.
C
.

.
C
.

.
C
.

In a straight chain alkane there are only single covalent bonds made up of
one pair of electrons joining one carbon atom to another carbon atom.
Lewis Structure
(electron dot diagram)
.

.
.

Valence Structure

.
.

In order to complete the octet of electrons around each carbon atom, any
unpaired electron will pair up with the valence electron from an atom
of hydrogen.

.
.

Valence Structure

..

..

..

.
.

.
.

.
.

..

..

..

Steps for Naming Straight Chain Alkanes

Lewis Structure
(electron dot diagram)

C-H

The name of an alkane is made up of two parts:

(i) a prefix or stem (first part of the name) : alk


(ii) a suffix (last part of the name) : ane

The name of a straight chain alkane always ends in the suffix ane

The first part of the name of a straight chain alkane, its prefix or stem, is
determined by the number of carbon atoms in the chain:

Number of
carbon atoms:

10

Prefix:

meth

eth

prop

but

pent

hex

hept

oct

non

dec

Step 1: Write the general name for your organic (carbon) compound (alkane)
Step 2: Number the carbon atoms in the carbon chain from left to right (or from right to left).
Step 3: Use the table of prefixes above to convert the number of carbon atoms to a prefix
Step 4: Substitute the alk prefix in the general name for the prefix determined by the number of
carbon atoms.
Example

Name the straight chain alkane shown below:


H
|
H

H
|
-

|
H

|
H

Step 1: Write the general name for your organic (carbon) compound
alkane (the name of straight chain alkanes always ends in "ane")

Step 2: Number the carbon atoms in the carbon chain from left to right (or from right to left).
H
|
H

C1
|
H

H
|
-

C2
|
H

Step 3: Use the table of prefixes above to convert the number of carbon atoms to a prefix
Number of carbon atoms:

Prefix:

eth

Step 4: Substitute the alk prefix in the general name for the prefix determined by the number of
carbon atoms.
General name :

alk

ane

Name of this alkane :

eth

ane

Steps for Drawing the Structure of Straight Chain Alkanes

Step 1: Divide the name of the straight chain alkane into a prefix and a suffix

Step 2: The suffix "ane" tells us that there are ONLY single covalent bonds between the carbon
atoms in the chain.
Step 3: Use the table above to convert the prefix to the number of carbon atoms in the carbon
chain
Step 4: Draw the required number of carbon atoms in a line with a dash (-) between each pair of
carbon atoms to represent the single covalent bond
Step 5: Place more dashes (- or | ) to represent other covalent bonds around each carbon atom so
that each carbon atom is surrounded by 4 dashes (covalent bonds)
Step 6: Place a hydrogen atom (H) at the end of any covalent bond (dash) that is not used to
bond to a carbon atom (C)
Example

Draw a structure1 for the straight chain alkane butane.

Step 1: Divide the name of the straight chain alkane into a prefix and a suffix
name: butane

prefix is but
suffix is ane
Step 2: The suffix ane tells us that there are ONLY single covalent bonds between the carbon
atoms in the chain.

Step 3: Use the table above to convert the prefix to the number of carbon atoms in the carbon
chain
Number of carbon atoms:

Prefix:

but

Step 4: Draw the required number of carbon atoms in a line with a dash (-) between each pair of
carbon atoms to represent the single covalent bond
C1

C2

C3

C4

Step 5: Place more dashes (- or | ) to represent other covalent bonds around each carbon atom so
that each carbon atom is surrounded by 4 dashes (covalent bonds)
|
-

Step 6: Place a hydrogen atom (H) at the end of any covalent bond (- or |) that is not used to
bond to a carbon atom (C)

Steps for Writing the Molecular Formula of Straight Chain Alkanes

A molecular formula tells us the number of atoms of each element present in a


molecule of the compound.

For an alkane, only two elements are present, carbon (C) and hydrogen (H).
When writing the molecular formula of an alkane, the number of carbon atoms is written before
the number of hydrogen atoms, that is, C is written before H
Step 1: Draw the structure of the alkane molecule.
Step 2: Write a skeleton molecular formula using the symbols for carbon (C) and hydrogen (H)

Step 3: Count the number of carbon atoms in the straight chain.


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).
Step 5: Count the number of hydrogen atoms in the straight chain.
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).
Step 7: Check that your completed molecular formula makes sense (CnH2n+2)
Example

Write the molecular formula for propane.

Step 1: Draw the structure of the alkane molecule.


propane
prefix or stem: prop means there are 3 carbon atoms (C) in the chain
suffix: ane means there are only single covalent bonds between carbon atoms in the chain (CC)
structure of propane:

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

Step 3: Count the number of carbon atoms in the straight chain.

C1
|

C2
|

C3
|

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).
C3H

Step 5: Count the number of hydrogen atoms in the straight chain.

H1

H2

H3

H4

H8

H7

H6

H5

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).
C3H8

Step 7: Check that your completed molecular formula makes sense (CnH2n+2)
propane: 3 carbon atoms so n=3
general alkane formula: CnH2n+2
for n=3: C3H2x3+2 which is C3H8
Animated YouTube Tutorial
Examples
Name

no. C atoms
(n)

no. H atoms
(2n + 2)

Formula
CnH2n+2

Structure
H
|

methane

(2 x 1) + 2 = 4

CH4

H-

-H

|
H

H
|

ethane

(2 x 2) + 2 = 6

C2H6

H-

C
|
H

H
|
-

C
|
H

-H

H
|

propane

(2 x 3) + 2 = 8

C3H8

H-

H
|

|
H

(2 x 4) + 2 = 10

C4H10

H-

(2 x 5) + 2 = 12

C5H12

H-

hexane

(2 x 6) + 2 = 14

C6H14

H-

H
|

H
|

- C

|
H

|
H

(2 x 7) + 2 = 16

C7H16

H
|

(2 x 8) + 2 = 18

C8H18

|
H

-H

|
H

H
|

H
|

- C - C

- C

|
H

H
|

|
H

H
|

-H

|
H

H
|

H
|

|
H

|
H

H
|

H
|

|
H

H
|

|
H

H
|

-H

|
H

H
|

H
|

|
H

H
|

|
H

H
|

|
H

H
|

|
H

H
|

|
H

H
|

H
|

|
H

H
|

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

H
|

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

octane

-H

C - C - C - C - C - C

H
|

H
|

H
|

|
H

heptane

H
|

|
H

H
|

C
|
H

H
|

|
H

pentane

|
H

H
|

butane

H
|

|
H

|
H

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

|
H

|
H

|
H

|
H

|
H

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).
1

No. carbon atoms


Prefix

meth eth prop but pent hex hept oct non

10
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
|
C
|
H

H-

H
|
C

H
|
C
|
H

-H

Identify the longest carbon chain containing the double bond.


H
|
C
|
H

H-

H
|
C

H
|
C

H
|
C

H
|
C
|
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

H-

H
|
C1
|
H

H
|
C2

H
|
C3

location of double bond: C2

numbering from right to left

H
|
C4
|
H

-H

OR

H-

H
|
C4
|
H

H
|
C3

H
|
C2

H
|
C1
|
H

-H

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
|
C
|
H

H
|
C2

H
|
C

infix is -2-

Determine the suffix for the name of the alkene.

H
|
C
|
H

-H

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-infixsuffix

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

prefix

infix

-n-

ene
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
prefix

-2-

ene

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.

C5

C6

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


-

C1

C2

C3

C4

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

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).

C2

C3

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

H-

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!
|

H
|
-

H
|
=

H
|
-

|
H

C
|
H

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
Cn H

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

Cn H y

The general molecular formula for a straight-chain alkene is C nH2n

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
|
-

|
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
|

C1

C2

H
|
-

C3

H
|
-

|
H

C4

-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
C4 H

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


H2

H3

H4

H5

|
H1-

|
-

|
-

|
H8

-H6

|
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 C nH2n

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
atoms
(n)

Systematic
IUPAC Name

ethene

prop-1-ene

but-1-ene

Other Names

ethylene
(preferred
IUPAC name)

Molecular
Formula

Structure

H
|

C2H4

H
|

|
H

|
H

H
|

1-propene
propene
propylene

C3H6

1-butene

C4H8

H
|

|
H

|
H

H
|
C

|
H

H
|
=

-H

H
|
-

-H

|
H

|
H
H
|

but-2-ene

2-butene

C4H8

H-

|
H

H
|

|
H

H
|

H
|

|
H

|
H

H
|

pent-1-ene

1-pentene

C5H10

H
|

|
H
H
|

2-pentene

C5H10

H
|

H-

|
H

H
|

|
H

H
|

C6H12

|
H

H
|

|
H
H
|

hex-2-ene

2-hexene

C6H12

H
|

|
H

H
|

C6H12

H
|

H
|

hept-1-ene

1-heptene

C7H14

H
|

|
H

|
H

H
|

H
|

H
|

|
H

|
H

|
H

H
|

H
|

H
|

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

H
|

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

H
|

3-hexene

|
H

H
|

|
H

|
H

hex-3-ene

-H

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

H
|

C - C = C - C - C

H
|

1-hexene

-H

|
H

H
|

|
H

hex-1-ene

H
|

C = C - C - C - C
|
H

pent-2-ene

-H

|
H

H
|

|
H

H
|

H
|

H
|

H
|

|
H

H
|

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

|
H

|
H

|
H

|
H

|
H

|
H

H
|

hept-2-ene

2-heptene

C7H14

H
|

H
|

H
|

H
|

3-heptene

C7H14

H
|

C8H16

C8H16

|
H

oct-4-ene

3-octene

C8H16

4-octene

C8H16

|
H

H
|

H
|

H
|

H
|

H
|

H
|

H
|

|
H

|
H

H
|

H
|

H
|

|
H
H
|

|
H
H
|

|
H
H
|

|
H
H
|

|
H
H
|

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

H
|

oct-3-ene

H
|

H
|

|
H

|
H

|
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
|

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

H
|

|
H

|
H

|
H

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

H
|

2-octene

|
H

|
H

H
|

|
H

oct-2-ene

H
|

|
H

|
H

H
|

1-octene

H
|

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

oct-1-ene

H
|

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

hept-3-ene

H
|

|
H

|
H

|
H

|
H

|
H

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

Key Concepts

Alkynes are hydrocarbons in which there is a triple bond between two carbon atoms1:
CC

The systematic IUPAC2 name of all simple straight-chain alkynes ends in "yne".

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


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

No. carbon atoms

meth eth prop but pent hex hept oct non

Prefix

10
dec

(ii) An infix which is a number that tells us the location of the triple bond (-n-)
(ii) The suffix yne telling us that a triple bond is present within the chain.

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

molecular
formula

structure

systematic IUPAC
name

trivial
name

Preferred IUPAC
Name

C2H2

H-C C-H

ethyne

acetylene

acetylene

Naming Straight-Chain Alkynes:

Identify the longest carbon chain containing the triple bond.

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

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

Determine the infix for the name of the alkyne based on the location of the triple
bond (use the lowest number out of the two carbon atoms joined by the triple 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 alkyne. All straight chain alkynes containing
one triple bond will end in "yne".

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

Example: Naming a Straight-Chain Alkyne


Give the systematic IUPAC name for this alkyne:
H-

H
|
C
|

H
|
C
|

-H

Identify the longest carbon chain containing the triple bond.


H
|
C
|
H

H-

H
|
C
|
H

-H

Determine the prefix for the name of the alkyne 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 triple bonded
carbon atoms have the lowest possible number.

numbering from left to right

H-

H
|
C1
|
H

C2

C3

numbering from right to left

H
|
C4
|
H

-H

OR

location of triple bond: C2

H
|
C4
|
H

H-

C3

C2

H
|
C1
|
H

-H

location of triple bond: C2

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

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

H-

H
|
C
|
H

C2

infix is -2-

Determine the suffix for the name of the alkyne.

H
|
C
|
H

All straight chain alkynes containing one double bond will end in "yne".
Suffix is yne

-H

Write the systematic IUPAC name for the alkyne in the form of prefix-infix-suffix
Systematic IUPAC name is but-2-yne
Another systematic name is 2-butyne

Drawing the structure5 of straight-chain alkynes:

Break the systematic IUPAC name of the alkyne into its three parts:
alk

prefix

-n-

infix

yne
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 triple bond using the infix.


We know there is a triple bond because the molecule's name has the suffix yne.

Draw a second and then a third dash, a second and third 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 triple bond have already used 3 out of
the 4 possible bonds in making the triple bond!

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

Example: Drawing the Structure of a Straight-Chain Alkyne


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

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

prefix

infix

-2-

yne
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.
-

C5

C6

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


-

C1

C2

C3

C4

Determine the location of the triple bond using the infix.


We know there is a triple bond because the molecule's name has the suffix yne.
Infix is 2, so this is the location of the triple bond.

C2

Draw a second and a third dash, a second and third 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 triple bond will occur between C2 and C3 (C2+1=3).

C2

C3

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

H-

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 triple bond have already used 3 out of
the 4 possible bonds in making the triple bond!
|

C
|

H
|
-

C
|

H
|
-

C
|

H
|
-

C
|

-H

Molecular formula of straight-chain alkynes:6

Draw the structure of the straight-chain alkyne.

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

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 alkyne is CnH2n-2


where n = number of carbon atoms in the carbon chain

Example: Writing the Molecular Formula of a Straight-Chain Alkyne


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

Draw the structure of the straight-chain alkyne.


H
|
H-

C
|
H

H
|
-

-H

|
H

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

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


H
|
H-

C1

C2

H
|

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
|
H1-

H3
|
-

|
H5

-H4

|
H6

total number of hydrogen atoms = y = 6

Write the number of hydrogen atoms as a subscript number to the right of the
symbol for carbon
C4H6

The general molecular formula for a straight-chain alkyne is CnH2n-2


where n = number of carbon atoms in the carbon chain
When n = 4 = number of carbon atoms in alkyne, then, the number of hydrogen
atoms in the alkyne will equal 2 x 4 -2 = 8 - 2 = 6

Animated Tutorial
Summary Table for Naming Straight-Chain Alkynes

no. C
atoms
(n)

Systematic
IUPAC Name

Other
Names

Molecular
Formula

ethyne

acetylene
(preferred
IUPAC name)

C2H2

Structure

H-

-H

H
|

prop-1-yne

1-propyne
propyne

C3H4

H-

-H

|
H

H
|

but-1-yne

1-butyne

C4H6

H-

H
|

|
H

2-butyne

C4H6

H-

H
|
-

|
H

1-pentyne

C5H8

H-

H
|

H
|

pent-2-yne

2-pentyne

C5H8

H-

hex-1-yne

1-hexyne

C6H10

H
|

|
H

|
H

H
|

H
|

C - C C - C - C
|
H

-H

C C - C - C - C
|
H

C
|
H

H
|

pent-1-yne

-H

|
H

H
|

but-2-yne

|
H

H
|

H
|

-H

-H

|
H

H
|

H
|

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

H
H
|

hex-2-yne

2-hexyne

C6H10

C6H10

C7H12

2-heptyne

C7H12

H
|

C7H12

C8H14

3-octyne

C8H14

|
H

|
H

H
|

H
|

H
|

H
|

|
H

|
H

|
H

H
|

H
|

H
|

|
H

H
|

H
|

|
H

H
|

H
|

|
H

H
|

|
H

|
H

|
H

|
H

|
H

H
|

H
|

H
|

H
|

H
|

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

oct-3-yne

H
|

H- C C - C - C - C - C - C - C -H

H
|

2-octyne

H
|

|
H

|
H

|
H

oct-2-yne

|
H

|
H

H
|

H
|

C8H14

H
|

|
H

8
1-octyne

H
|

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

oct-1-yne

H
|

H- C - C C - C - C - C - C -H

H
|

3-heptyne

|
H

H- C C - C - C - C - C - C -H

|
H

hept-3-yne

|
H

|
H

H
|

hept-2-yne

H
|

|
H

|
H

H
|

H- C - C - C C - C - C -H

H
|

1-heptyne

H
|

H
|

|
H

hept-1-yne

|
H

H
|

3-hexyne

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

hex-3-yne

H
|

|
H
H
|

|
H

|
H

|
H

|
H

H
|

H
|

H
|

H
|

H- C - C - C C - C - C - C - C -H

oct-4-yne

4-octyne

C8H14

|
H

|
H

H
|

H
|

|
H
H
|

|
H

|
H

|
H

H
|

H
|

H
|

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

|
H

|
H

|
H

|
H

|
H

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 ensuffix 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 sidechains). 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
(Lewis Structure)

H
..
H:
C
..
H
methane

:H

alkyl group
(Lewis Structure)

remove H.

H
..
.
C
..
H
methyl

:H

alkyl group
(Valence Structure)

H
|
C
|
H

-H

methyl

Lewis Structures (electron dot diagrams)


Lewis Structures of Atoms

The chemical symbol for the atom is surrounded by a number of dots corresponding to the
number of valence electrons.

Number
of
Valence
Electrons

Example

Lewis
Structure
(electron
dot

Group
Group
Group
18
2
1
Group Group Group Group Group 17 except
Hydrogen
Helium (alkali
(Alkali
13
14
15
16 (Halogens) Helium
earth
metals)
(Noble
metals)
Gases)

diagram)

Lewis Structures for Ions of Elements

The chemical symbol for the element is surrounded by the number of valence electrons present
in the ion.
The whole structure is then placed within square brackets, with a superscript to indicate the
charge on the ion.

Atoms will gain or lose electrons in order to achieve a stable, Noble Gas (Group 18), electronic
configuration.

Negative ions (anions) are formed when an atom gains electrons.

Positive ions (cations) are formed when an atom loses electrons.

Charge
on Ion

1+

No.
electrons
gained or
lost

1e lost

Example

Lewis
Structure
(electron
dot
diagram)

H+

2+

3+

4+

2e lost 3e lost 4e lost

4-

3-

2-

4e
3e
2e
gained gained gained

1-

1e gained

Group
Group
2 2+
1+
Group Group Group Group Group Group 17 H(alkali
3+
4+
432(Alkali
13
14
14
15
16
(Halogens) (hydride)
earth
metals)
metals)

OR H+ OR Li+

OR
Be2+

OR B3+ OR C4+

Lewis Structures for Ionic Compounds

The overall charge on the compound must equal zero, that is, the number of electrons lost by
one atom must equal the number of electrons gained by the other atom.

The Lewis Structure (electron dot diagram) of each ion is used to construct the Lewis Structure
(electron dot diagram) for the ionic compound.

Examples
Lithium fluoride, LiF

Lithium atom loses one electron to form the cation Li+

Fluorine atom gains one electron to form the anion F-

Lithium fluoride compound can be represented as

Li+

OR

Lithium oxide, Li2O

Each lithium atom loses one electron to form 2 cations Li+ (2 electrons in total are lost)

Oxygen atom gains two electrons to form the anion O2-

Lithium oxide compound can be represented as

2Li+

OR

Li+

Li+ OR

Lewis Structures for Covalent Compounds

In a covalent compound, electrons are shared between atoms to form a covalent bond in order
that each atom in the compound has a share in the number of electrons required to provide a
stable, Noble Gas, electronic configuration.

Electrons in the Lewis Structure (electron dot diagram) are paired to show the bonding pair of
electrons.

Often the shared pair of electrons forming the covalent bond is circled

Sometimes the bond itself is shown (-), these structures can be referred to as valence
structures.

Examples
hydrogen fluoride, HF

Hydrogen atom has 1 valence electron

Fluorine atom has 7 valence electrons

Hydrogen will share its electron with fluorine to form a bonding pair of electrons (covalent bond)
so that the hydrogen atom has a share in 2 valence electrons (electronic configuration of
helium) and fluorine has a share in 8 valence electrons (electronic configuration of neon)

Lewis Structure (electron dot diagram) for hydrogen fluoride

OR

Valence Structure for hydrogen fluoride

ammonia, NH3

Nitrogen atom has 5 valence electrons

Hydrogen atom has 1 valence electron

Each of the 3 hydrogen atoms will share its electron with nitrogen to form a bonding pair of
electrons (covalent bond) so that each hydrogen atom has a share in 2 valence electrons
(electronic configuration of helium) and the nitrogen has a share in 8 valence electrons (electron
configuration of neon)

Lewis Structure (electron dot diagram) for ammonia

OR

Valence Structure for ammonia

oxygen molecule, O2

Each oxygen atom has 6 valence electrons

Each oxygen will share 2 of its valence electrons in order to form 2 bonding pairs of electrons (a
double covalent bond) so that each oxygen will have a share in 8 valence electrons (electronic
configuration of neon).

Lewis Structure (electron dot diagram) for the oxygen molecule

OR

Valence structure for the oxygen molecule

Lewis Structures (electron dot diagrams)


Lewis Structures of Atoms

The chemical symbol for the atom is surrounded by a number of dots corresponding to the
number of valence electrons.

Number
of
Valence
Electrons
Example

Hydrogen Group Helium Group Group Group Group Group Group 17

Group

2
(alkali
earth
metals)

1
(Alkali
metals)

13

14

15

16

18
except
(Halogens) Helium
(Noble
Gases)

Lewis
Structure
(electron
dot
diagram)

Lewis Structures for Ions of Elements

The chemical symbol for the element is surrounded by the number of valence electrons present
in the ion.
The whole structure is then placed within square brackets, with a superscript to indicate the
charge on the ion.

Atoms will gain or lose electrons in order to achieve a stable, Noble Gas (Group 18), electronic
configuration.

Negative ions (anions) are formed when an atom gains electrons.

Positive ions (cations) are formed when an atom loses electrons.


1+

Charge
on Ion
No.
electrons
gained or
lost

Example

Lewis
Structure
(electron
dot
diagram)

1e lost

H+

2+

3+

4+

2e lost 3e lost 4e lost

4-

3-

2-

4e
3e
2e
gained gained gained

1-

1e gained

Group
Group
2 2+
1+
Group Group Group Group Group Group 17 H(alkali
3+
4+
432(Alkali
13
14
14
15
16
(Halogens) (hydride)
earth
metals)
metals)

OR H+ OR Li+

OR
Be2+

OR B3+ OR C4+

Lewis Structures for Ionic Compounds

The overall charge on the compound must equal zero, that is, the number of electrons lost by
one atom must equal the number of electrons gained by the other atom.

The Lewis Structure (electron dot diagram) of each ion is used to construct the Lewis Structure
(electron dot diagram) for the ionic compound.

Examples
Lithium fluoride, LiF

Lithium atom loses one electron to form the cation Li+

Fluorine atom gains one electron to form the anion F-

Lithium fluoride compound can be represented as

Li+

OR

Lithium oxide, Li2O

Each lithium atom loses one electron to form 2 cations Li+ (2 electrons in total are lost)

Oxygen atom gains two electrons to form the anion O2-

Lithium oxide compound can be represented as

2Li+

OR Li+

Li+ OR

Lewis Structures for Covalent Compounds

In a covalent compound, electrons are shared between atoms to form a covalent bond in order
that each atom in the compound has a share in the number of electrons required to provide a
stable, Noble Gas, electronic configuration.

Electrons in the Lewis Structure (electron dot diagram) are paired to show the bonding pair of
electrons.

Often the shared pair of electrons forming the covalent bond is circled

Sometimes the bond itself is shown (-), these structures can be referred to as valence
structures.

Examples
hydrogen fluoride, HF

Hydrogen atom has 1 valence electron

Fluorine atom has 7 valence electrons

Hydrogen will share its electron with fluorine to form a bonding pair of electrons (covalent bond)
so that the hydrogen atom has a share in 2 valence electrons (electronic configuration of
helium) and fluorine has a share in 8 valence electrons (electronic configuration of neon)

Lewis Structure (electron dot diagram) for hydrogen fluoride

OR

Valence Structure for hydrogen fluoride

ammonia, NH3

Nitrogen atom has 5 valence electrons

Hydrogen atom has 1 valence electron

Each of the 3 hydrogen atoms will share its electron with nitrogen to form a bonding pair of
electrons (covalent bond) so that each hydrogen atom has a share in 2 valence electrons
(electronic configuration of helium) and the nitrogen has a share in 8 valence electrons (electron
configuration of neon)

Lewis Structure (electron dot diagram) for ammonia

OR

Valence Structure for ammonia

oxygen molecule, O2

Each oxygen atom has 6 valence electrons

Each oxygen will share 2 of its valence electrons in order to form 2 bonding pairs of electrons (a
double covalent bond) so that each oxygen will have a share in 8 valence electrons (electronic
configuration of neon).

Lewis Structure (electron dot diagram) for the oxygen molecule

OR

Valence structure for the oxygen molecule

(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-infixyl:

alkane
(Lewis Structure)

alkyl group
(Lewis Structure)

alkyl group
(Valence Structure)

H H H H
..
.. ..
..
H: C : C : C : C :H
..
.. ..
..
H H H H
butane

H H H
.. .. ..
H: C : C : C :
remove H.
.. .. .
H H
butan-2-yl

H
H H H
..
|
|
|
C :H H- C - C - C ..
|
|
|
H
H H
butan-2-yl

H
|
C -H
|
H

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

Cl

Br

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-infixmultiplyingiodo

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-infixmultiplyingmethyl

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)

esters

-CO-O-C

(functional naming rather than substitutive naming is


preferred)
(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)

Naming Straight-Chain Alkanoic Acids


Key Concepts

Alkanoic acids are organic molecules containing only carbon (C), hydrogen (H) and
oxygen (O) atoms.

Alkanoic acids belong to the group of organic compounds known as carboxylic acids.

All alkanoic acids contain the carboxyl1 (COOH) functional group.


O
||

-OH

A straight-chain alkanoic acid consists of a chain of 1 or more carbon atoms joined to


each other by single covalent bonds, with an OH and a =O functional group attached to
a terminal (end) carbon atom in the chain.

Numbering of the carbon chain begins with the carbon atom of the carboxyl functional
group.

The systematic IUPAC name2 of an alkanoic acid is made up of two parts:


(i) a prefix or stem
(the name of the parent hydrocarbon (the alkane chain) without the "e"
ending,alkan)
(ii) a suffix
(last part of the name, oic acid)

The suffix when naming a straight-chain alkanoic acid is always "oic acid"

The prefix or stem is dependent on the number of carbon atoms in the longest chain of
carbon atoms (the parent hydrocarbon, or parent alkane):

Number of
carbon atoms:

10

Prefix:

meth

eth

prop

but

pent

hex

hept

oct

non

dec

The general molecular formula for a straight-chain alkanoic acid is CnH2nO2

where n = number of carbon atoms in the carbon chain


Steps for Naming Straight Chain Alkanoic Acids

The systematic IUPAC name of an alkanoic acid is made up of two parts:


(i) a prefix or stem (first part of the name, the name of the parent alkane without
the "e" ending) : alkan
(ii) a suffix (last part of the name indicating the presence of the COOH functional
group) : oic acid

The name of a straight chain alkanoic acid always ends in the suffix oic acid

The first part of the name of a straight chain alkanoic acid, its prefix or stem, is
determined by the number of carbon atoms in the parent alkane chain:

Number of
carbon atoms:

10

Prefix:

meth

eth

prop

but

pent

hex

hept

oct

non

dec

Step 1: Identify the longest carbon chain containing the COOH (carboxyl) functional group.
Step 2: Number each carbon atom along the longest carbon chain so that the carbon atom of
the COOH (carboxyl) functional group has the number 1.
Step 3: Determine the prefix for the name of the alkanoic acid based on the number of
carbon atoms in the chain.
(The name of the parent alkane without the "e" ending)
Step 4: Determine the suffix for the name of the alkanoic acid.
All straight chain alkanoic acids containing one COOH (carboxyl) functional group will end in
"oic acid".
Step 5: Write the name for the alkanoic acid in the form of prefixsuffix
Example: 1 Carbon Atom
Name the straight chain alkanoic acid shown below:
O
||
H-

OH

Step 1: Identify the longest carbon chain containing the COOH (carboxyl) functional group.

O
||
H-

OH

Step 2: Number each carbon atom along the longest carbon chain so that the carbon atom of
the COOH (carboxyl) functional group has the number 1.
O
||
H-

C1

OH

Step 3: Determine the prefix for the name of the alkanoic acid based on the number of
carbon atoms in the chain.
(The name of the parent alkane without the "e" ending)
Longest carbon chain has 1 carbon atom.
Parent hydrocarbon is methane.
Prefix is methan
Step 4: Determine the suffix for the name of the alkanoic acid.
All straight chain alkanoic acids containing one COOH (carboxyl) functional group will end in
"oic acid".
Suffix is oic acid
Step 5: Write the name for the alkanoic acid in the form of prefixsuffix
Systematic IUPAC name is methanoic acid
(Preferred IUPAC name is formic acid.)
Example: 2 Carbon Atom Chain
Name the straight chain alkanoic acid shown below:
H
|
H-

O
||
-

OH

|
H
Step 1: Identify the longest carbon chain containing the COOH (carboxyl) functional group.
H
|
H-

O
||
-

OH

|
H
Step 2: Number each carbon atom along the longest carbon chain so that the carbon atom of
the COOH (carboxyl) functional group has the number 1.
H
|
H-

O
||

C2

C1

OH

|
H
Step 3: Determine the prefix for the name of the alkanoic acid based on the number of
carbon atoms in the chain.
(The name of the parent alkane without the "e" ending)
Longest carbon chain has 2 carbon atoms.
Parent hydrocarbon is ethane.
Prefix is ethan
Step 4: Determine the suffix for the name of the alkanoic acid.
All straight chain alkanoic acids containing one COOH (carboxyl) functional group will end in
"oic acid".
Suffix is oic acid
Step 5: Write the name for the alkanoic acid in the form of prefixsuffix
Systematic IUPAC name is ethanoic acid
(Preferred IUPAC name is acetic acid.)
Example: 3 Carbon Atom Chain
Name the straight chain alkanol shown below:
H
|
H-

C
|
H

H
|
-

C
|
H

H
|
-

OH

|
H

Step 1: Identify the longest carbon chain containing the COOH (carboxyl) functional group.
H
|

H
|

O
||

H-

|
H

OH

|
H

Step 2: Number each carbon atom along the longest carbon chain so that the carbon atom of
the COOH (carboxyl) functional group has the number 1.
H
|
H-

C3
|
H

H
|
-

C2

O
||
-

C1

OH

|
H

Step 3: Determine the prefix for the name of the alkanoic acid based on the number of
carbon atoms in the chain.
(The name of the parent alkane without the "e" ending)
Longest carbon chain has 3 carbon atoms.
Parent hydrocarbon is propane.
Prefix is propan
Step 4: Determine the suffix for the name of the alkanoic acid.
All straight chain alkanoic acids containing one COOH (carboxyl) functional group will end in
"oic acid".
Suffix is oic acid
Step 5: Write the name for the alkanoic acid in the form of prefixsuffix
Systematic IUPAC name is propanoic acid
(Preferred IUPAC name is also propanoic acid.)
Steps for Drawing the Structure3 of Straight Chain Alkanoic Acids
Step 1: Break the systematic IUPAC name of the alkanoic acid into its two parts:
alkanoic acid
prefix

suffix

Step 2: Determine the number of carbon atoms in the longest alkane carbon chain using
theprefix.
Step 3: Draw a chain of carbon atoms of the required length using dashes to represent a
single covalent bond between each pair of carbon atoms.

Step 4: For the "oic acid" suffix, on the first carbon atom, draw 2 vertical lines connected to
an O atom (representing the double bonded oxygen atom), and a horizontal dash to the OH
group (covalently bonded hydroxyl group).
Step 5: Place dashes representing single covalent bonds around the other carbon atoms in
the chain so that each of these carbon atoms is surrounded by 4 dashes.
Step 6: Complete the structure by placing a hydrogen atom (H) at the end of all the vacant
dashes.
Example
Draw a structure for butanoic acid.
Step 1: Break the systematic IUPAC name of the alkanoic acid into its two parts:
butanoic acid
prefix

suffix

Step 2: Determine the number of carbon atoms in the longest alkane carbon chain using
theprefix.
Prefix is butan, therefore this alkanoic acid has 4 carbon atoms in the chain.
Step 3: 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

Step 4: For the "oic acid" suffix, on the first carbon atom, draw 2 vertical lines connected to
an O atom (representing the double bonded oxygen atom), and a horizontal dash to the OH
group (covalently bonded hydroxyl group).
O
||
HO-

Step 5: Place dashes representing single covalent bonds around the other carbon atoms in
the chain so that each of these carbon atoms is surrounded by 4 dashes.
O
||
HO-

|
-

|
-

|
-

Step 6: Complete the structure by placing a hydrogen atom (H) at the end of all the vacant
dashes.
O

||
HO-

|
-

|
-

|
H

|
-

|
H

-H

|
H

Steps for Writing the Molecular Formula of Straight Chain Alkanoic Acids
A molecular formula tells us the number of atoms of each element present in a molecule of the
compound.
For a straight-chain alkanoic acid, only three elements are present, carbon (C), hydrogen (H)
and oxygen (O).
When writing the molecular formula of an alkanoic acid, the number of carbon atoms is written
before the number of hydrogen atoms which is written before the number of oxygen atoms,
that is, C is written before H which is written before O4.
A straight chain alkanoic acid will always have 2 oxygen atoms.
CxHyO2
Step 1: Draw the structure of the alkanoic acid molecule.
Step 2: Write a skeleton molecular formula using the symbols for carbon (C), hydrogen (H)
and oxygen (O).
CHO
Step 3: Count the number of carbon atoms in the alkanoic acid 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).
Step 5: Count the number of hydrogen atoms in the alkanoic acid 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).
Step 7: Count the number of oxygen atoms in the alkanoic acid molecule.
Step 8: Write the number of of oxygen atoms into the skeleton molecular formula as a
subscript number to the right of the symbol for oxygen (O).
Note: if only one carboxyl (COOH) group is present, the number of oxygen atoms is 2, and
the subscript 2 is included in the molecular formula.
Step 9: Check that your completed molecular formula makes sense (C nH2nO2)
Example
Write the molecular formula for pentanoic acid.

Step 1: Draw the structure of the alkanoic acid molecule.


O

||
HO-

|
-

|
-

-H

Step 2: Write a skeleton molecular formula using the symbols for carbon (C), hydrogen (H)
and oxygen (O).
CHO
Step 3: Count the number of carbon atoms in the alkanoic acid molecule.
O

H
||

HO-

H
|

C1

H
|

C2

C3

H
|

C4

C5

-H

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).
C5H O
Step 5: Count the number of hydrogen atoms in the alkanoic acid molecule.
O

H2
||

HO-

H3
|

H4
|

H5
|

|
-

H10

H9

H8

H7

-H6

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).
C5H10O
Step 7: Count the number of oxygen atoms in the alkanoic acid molecule:
O2

||
HO1-

|
-

|
-

-H

Step 8: Write the number of of oxygen atoms into the skeleton molecular formula as a
subscript number to the right of the symbol for oxygen (O).
2 oxygen atoms are present in this molecule.
Molecular formula for pentanoic acid is C5H10O2
Step 9: Check that your completed molecular formula makes sense (C nH2nO2)
n = number of carbon atoms = 5
number of hydrogen atoms = 2 x n = 2 x 5 = 10
number of oxygen atoms = 2
Summay Table: Molecular Formula, Structure and Name of Some Alkanoic Acids
no. C atoms Molecular Formula
(n)
CnH2nO2
1

O
||

CH2O2
H

H
|

C2H4O2

Preferred IUPAC Name


(alternative name)

Structure

formic acid
(methanoic acid)

OH

O
||

OH

acetic acid
(ethanoic acid)

- OH

propanoic acid
(propionic acid)

|
H

C3H6O2

H
|

H
|

O
||

- C

- C

- C

|
H

|
H

H
|

C4H8O2

H
|

O
||

- C - C - C

- C

|
H

H
|

|
H

|
H

- OH

butanoic acid
(butyric acid)

H
|

C5H10O2

H
|

H
|

C6H12O2

|
H

H
|

|
H

H
|

- OH

pentanoic acid

|
H

H
|

H
|

O
||
- OH

hexanoic acid

H - C - C - C - C - C - C - C - OH

heptanoic acid

H
|

C7H14O2

O
||

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

H
|

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

H
|

|
H

|
H

H
|

|
H

|
H

H
|

|
H

|
H

H
|

|
H

|
H

H
|

|
H

H
|

O
||

|
H

H H H H H H H O
| | | | | | | ||

C8H16O2

H - C - C - C - C - C - C - C - C - OH

octanoic acid

| | | | | | |
H H H H H H H

H H H H H H H H O
| | | | | | | | ||

C9H18O2

H - C - C - C - C - C - C - C - C - C - OH

nonanoic acid

| | | | | | | |
H H H H H H H H

H H H H H H H H H O
| | | | | | | | | ||

10

C10H20O2

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

decanoic acid