Professional Documents
Culture Documents
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.
prefix suffix
The principal nomenclature used in organic chemistry, and which forms the basis of
most IUPAC3preferred names, is substitutive nomenclature.
prefix
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
Parent Hydrocarbon
The parent hydrocarbon can be
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:
Key Concepts
A single covalent bond joins one carbon atom in the chain to another carbon
atom.
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
Alkanes are hydrocarbons, that is, alkanes are compounds containing ONLY carbon
and hydrogen atoms.
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
..
..
..
.
.
.
.
.
.
..
..
..
Lewis Structure
(electron dot diagram)
C-H
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
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
eth
ane
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
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)
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 2: Write a skeleton molecular formula using the symbols for carbon (C) and hydrogen (H)
CH
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
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
|
H
|
H
|
H
|
H
|
H
Key Concepts
(i) A prefix which tells us how many carbon atoms are in the chain (alk).
1
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:
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".
Example
H-
H
|
C
H
|
C
|
H
-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.
Number each carbon atom along the longest carbon chain so that the double
bonded carbon atoms have the lowest possible number.
H-
H
|
C1
|
H
H
|
C2
H
|
C3
H
|
C4
|
H
-H
OR
H-
H
|
C4
|
H
H
|
C3
H
|
C2
H
|
C1
|
H
-H
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-
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
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 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
C1
C2
C3
C4
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).
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
Write a skeletal molecular formula using the symbols for carbon and
hydrogen:
C H
Write the number of carbon atoms as a subscript number to the right of the
symbol for carbon
Cn H
Cn H y
Write the molecular formula for the molecule with the systematic IUPAC name of
but-1-ene.
H
|
H
|
-
H
|
-
|
H
-H
|
H
Write a skeletal molecular formula using the symbols for carbon and
hydrogen:
C H
H
|
C1
C2
H
|
-
C3
H
|
-
|
H
C4
-H
|
H
Write the number of carbon atoms as a subscript number to the right of the
symbol for carbon
C4 H
H3
H4
H5
|
H1-
|
-
|
-
|
H8
-H6
|
H7
C4H8
The general molecular formula for a straight-chain alkene is C nH2n
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
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".
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
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".
H
|
C
|
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.
H-
H
|
C1
|
H
C2
C3
H
|
C4
|
H
-H
OR
H
|
C4
|
H
H-
C3
C2
H
|
C1
|
H
-H
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-
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
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.
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.
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
C1
C2
C3
C4
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
Write a skeletal molecular formula using the symbols for carbon and hydrogen:
C
Write the number of carbon atoms as a subscript number to the right of the symbol
for carbon
CnH
Write the number of hydrogen atoms as a subscript number to the right of the
symbol for carbon
CnHy
C
|
H
H
|
-
-H
|
H
Write a skeletal molecular formula using the symbols for carbon and hydrogen:
C
C1
C2
H
|
C3
C4
|
H
-H
|
H
Write the number of carbon atoms as a subscript number to the right of the symbol
for carbon
C4H
H3
|
-
|
H5
-H4
|
H6
Write the number of hydrogen atoms as a subscript number to the right of the
symbol for carbon
C4H6
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 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
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)
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.
Charge
on Ion
1+
No.
electrons
gained or
lost
1e lost
Example
Lewis
Structure
(electron
dot
diagram)
H+
2+
3+
4+
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+
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
Li+
OR
Each lithium atom loses one electron to form 2 cations Li+ (2 electrons in total are lost)
2Li+
OR
Li+
Li+ OR
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 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)
OR
ammonia, NH3
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)
OR
oxygen molecule, O2
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).
OR
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
Group
2
(alkali
earth
metals)
1
(Alkali
metals)
13
14
15
16
18
except
(Halogens) Helium
(Noble
Gases)
Lewis
Structure
(electron
dot
diagram)
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.
Charge
on Ion
No.
electrons
gained or
lost
Example
Lewis
Structure
(electron
dot
diagram)
1e lost
H+
2+
3+
4+
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+
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
Li+
OR
Each lithium atom loses one electron to form 2 cations Li+ (2 electrons in total are lost)
2Li+
OR Li+
Li+ OR
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 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)
OR
ammonia, NH3
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)
OR
oxygen molecule, O2
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).
OR
(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.
Cl
Br
Name of Element
fluorine
chlorine
bromine
iodine
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
The functional groups you are most likely to meet during an introductory chemistry
course are:
type
formula
nomenclature
carboxylic
acids
esters
-CO-O-C
aldehydes
ketones
alcohols
OH
amines
NH2
amides
CO-NH2
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.
-OH
Numbering of the carbon chain begins with the carbon atom of the carboxyl functional
group.
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 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.
||
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
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