ORGANIC CHEMISTRY

-Organic molecules
contain only C, H, O, N
and sometimes S and P

-56 204 570 organic

substances have been
recorded
What allows for the diversity of organic compounds?
-Carbon can make 4 bonds
-The 4 bonds can be a combination of single, double,
and triple bonds

methane, CH4 methanal, CH2O

ethanenitrile, CH3CN
Naming Hydrocarbons
 What’s in a Name
Assembled from components that describe various
features of the molecule.

root suffix

Functional
Number of group
carbons in the
longest chain

Ex: methane

Ex: butanol
 Root Name = Longest Chain
• The longest continuous chain of carbons containing
the principal functional group defines the root name.

• Other groups attached to this chain are called

substituents.
Longest Carbon Chain Name
meth- = 1 carbon
eth- =2
prop- =3
but- =4
pent- =5
hex- =6
hept- =7
oct- =8
non- =9
dec- = 10
undec- = 11
dodec- = 12
Just FYI…
13 trideca- 30 triaconta- 500 pentacta- 7000 heptalia-

14 tetradeca- 40 tetraconta- 600 hexacta 8000 octalia-

15 pentadeca 50 pentaconta- 700 heptacta- 9000 nonalia-

16 hexadeca- 60 hexaconta- 800 octacta-
17 heptadeca 70 heptaconta- 900 nonacta-
18 octadeca- 80 octaconta- 1000 kilia-
19 nonadeca- 90 nonaconta- 2000 dilia-
20 icosa- 100 hecta- 3000 trilia-
21 heneicosa 200 dicta- 4000 tetralia-

22 docosa 300 tricta- 5000 pentalia-

23 tricosa 400 tetracta- 6000 hexalia-

 Principal Functional Group =
Suffix
• The principal functional group is used to define the
class the compound belongs to e.g. an alkene, alcohol,
etc.
• Determines the suffix of molecule’s name

• Refer to ‘Families of Organic Compounds’ handout

 Basic Naming Rules
The IUPAC systematic name of an organic compound can
be constructed based on a series of steps and rules:

1. Identification of the principal functional group and

substituents

2. Identification of the longest continuous chain

containing the principal functional group.

3. Assign locants (i.e. numbers) to the principal

functional group and substituents.
First Set of Functional
Groups:

HYDROCARBONS
 Hydrocarbons:

When an organic molecule is composed only of hydrogen and

carbon, it is called a hydrocarbon:

_________: Hydrocarbons with single bonds

_________: Hydrocarbons with double bond(s)

_______: Hydrocarbons with triple bond(s)

-Characterized by C-C single bonds

-Also known as _________________

-empirical formula = ________

 CnH2n+2, n=8
= ______
Properties:
-Hydrophobic (does not mix with water and other polar
substances)

-Generally low boiling points (due to weak London Dispersion

Forces)

- Longer alkane molecules have higher boiling points

Some IUPAC* names of alkanes:

ethane propane butane

All alkanes have the suffix “____”

*International Union of Pure and Applied Chemistry

 ALKANES
IUPAC naming system:
Molecular
formula Condensed Structural Formula Name

CH4 CH4 methane

C2H6 CH3CH3 ethane
C3H8 CH3CH2CH3 propane
C4H10 CH3CH2CH2CH3 butane
C5H12 CH3CH2CH2CH2CH3 pentane
C6H14 CH3CH2CH2CH2CH2CH3 hexane
C7H16 CH3CH2CH2CH2CH2CH2CH3 heptane
C8H18 CH3CH2CH2CH2CH2CH2CH2CH3 octane
C9H20 CH3CH2CH2CH2CH2CH2CH2CH2CH3 nonane
C10H22 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 decane
 ALKANES
IUPAC naming system:

Name the following alkanes:

1 2 3 4 5 6 1 2 3 4 5 6 7 8 9
 Substituents: Branches in
Chains
Not all alkanes are straight chains. Some alkanes
have alkyl side groups (alkyl substituents) attached.
-CH3 methyl
Ex:
-C2H5 ethyl
-C3H7 propyl methyl group

-C4H9 butyl
-C5H11 pentyl
-C6H13 hexyl
-C7H15 heptyl
-C8H17 octyl

name:
IUPAC naming system:
For alkanes with side groups…

Substituent(s) prefix suffix

family
Branches Number of
carbons in the
longest chain

Ex: 2-methylbutane
 Assigning Locants (i.e.
numbering)
• The numbers that define the positions of the principal
functional group and substituents are called locants.

• Compounds are numbered from one end of the longest

continuous chain.

• The locants are assigned such that the principal

functional group gets the lowest possible locant
IUPAC naming system:
Name the following branched alkanes

1 2 3 4 5 1 2 3 4 5

2-methylpentane 3-methylpentane

When there is ambiguity, the substituent

must be numbered according to the carbon
atom that it is attached to
(aim to get the lowest possible number)
First Point of Difference:
Which name is incorrect?

1 2 3 4 5 5 4 3 2 1

2-methylpentane 4-methylpentane

Aim for the lowest possible number when

counting.
For alkanes with multiple branches of the same kind
attached to the main chain….

• give each branch a number.

• list the numbers in ascending order.
• give the branch name a multiplying prefix (i.e.
di, tri, tetra, etc.) to indicate the number of
identical branches.
• put commas between numbers, and hyphens
between numbers and letters. No space!

Ex: 4,6-dimethylhept ane

 IUPAC naming system:
Name the following branched alkane

1. Find the longest

continuous chain
CH3 - CH - CH3
of C atoms |
(parent chain)
CH3 - CH - CH2
2. Identify any |
substitutents
CH3
IUPAC naming system:
For alkanes with multiple, but different kinds of
branched groups…

• name the branched groups in alphabetical

order.
• give the branch name a number to indicate
which carbon in the main chain it is bonded
with.
• put commas between numbers, and hyphens
between numbers and letters.

Ex: 4-ethyl-6-methylhept ane

 CH3
|
CH2 - CH2
|
CH2 - CH - CH2 - CH3
|
CH - CH3
|
CH3
 Numbering (con’t)
• If numbering a functional group results in a "tie" then the
first point of difference rule. The first time a difference
in numbering occurs, then the method that gives the
lower number at this first difference is used.

• In the event that there is no first point of difference then

alphabetisation is used.
IUPAC naming system:
Name the following branched alkane

The order of
substituents in the
name is based on
alphabetical order
Drawing alkanes:
3 types of diagrams—all showing the same molecule

Structural diagram

Condensed diagram CH3CH2CH2CH2CH2CH3

Line diagram
Drawing alkanes:
Line diagrams:

2 4 6

1 3 5

Every end or point on a line diagram

represents a carbon atom. Hydrogen
atoms are not shown.
Drawing alkanes:
Draw the following alkanes using line diagrams

2-methylbutane 3-ethyl-3,4-dimethylheptane
 Nomenclature of Alkanes

Write the structure of 3-ethyl-2-methylpentane.

 No First Point of Difference
• In the event that there is no first point of difference then
alphabetisation is used to determine numbering.
• Name this alkane: 3-ethyl-6-methyloctane

2 4 8 NOT
1 7 3 5 6 7 1 6-ethyl-3-methyloctane
5
8 6 4 3 2

• Two branches occur at C-3 and C-6, regardless of how the parent
chain is numbered
 2 4 8
1 7 3 5 6 7 1
5
8 6 4 3 2

This time, there is a first point of difference at C-4

6-ethyl-3,4-dimethyloctane
 Condensed Diagrams
• Bonds are (usually) not drawn. Only atoms
are drawn
• Entire molecule is written in one line (even
branches)
• Repeated fragments are simplified with
brackets
• Branches are also indicated with brackets.
Structural diagram
Condensed diagram

CH3CH2CH2CH2CH2CH3

CH3(CH2)4CH3
Condensed diagram
 CH3
|
CH2 - CH2
| BE CAREFUL! A bracket to
CH2 - CH - CH2 - CH3 indicate a branch can be easily
confused with a repeated
| fragment. Typically brackets
such as (CH3) indicate a
CH - CH3 branch, while brackets such as
| (CH2) indicate a repeated
fragment that’s part of a main
CH3 chain

1 2 3 4 5 6 7
CH3CH(CH3)CH(CH2CH3)CH2CH2CH2CH3

CH3CH(CH3)CH(CH2CH3)(CH2)3CH3
 It is common practice to
draw the multiple bond in
the condensed formula, but
the bond can be omitted
when its placement will be
obvious

OH

O Br

O
CYCLOALKANES
-Ring-like structures of alkanes

-empirical formula = CnH2n

 CnH2n, n=6
= C6H12
IUPAC naming system:

Name the following alkanes:

cyclobutane cyclooctane cyclopentane

The prefix “cyclo” is added to the alkane name

IUPAC naming system:

Name the following alkanes:

CH3CH2CH2
CH CH2

CH2 CH2

propylcyclobutane

Numbering the lcoation is not required, since the number is implied

 3
3

1 1
1 1
3 3

If there are several substituents, the numbering of ring carbons then continues
in a direction (clockwise or counter-clockwise) that affords the second
substituent the lower possible location number

If two different substituents are present on the ring, they are listed in
alphabetical order, and the first cited substituent is assigned to carbon #1.
 2 3

1 4

6 5

The disubstituted carbon becomes #1 because the total locator

numbers are thereby kept to a minimum. The methyl substituent is
then located on carbon #2 (clockwise numbering), and the ethyl
group is located on #4
IUPAC naming system:

Draw the following alkanes using line structures:

1,1-dipropylcyclopropane 1-ethyl-1,2,5-trimethylcyclopentane
HALOALKANES
-Alkanes with halogen atoms

-Also known as alkyl halides

IUPAC naming system:

Halogen groups: -F fluoro

-Cl chloro
-Br bromo
-I iodo

Just like alkyl substituents, the halogens are placed at the

beginning of the name, and are ordered alphabetically.
IUPAC naming system:

Name the following haloalkanes:

STRUCTURAL ISOMERS
Compounds with the same molecular formula
but with different bonding arrangements are
structural isomers.

Butane isomers Pentane isomers

Ex: Structural isomers of hexane + boiling points

Changing the structure affects the boiling point

This structure can easily stack and form more London Dispersion Forces
with neighbouring hexane molecules
Draw all of the structural isomers of heptane using
line structures:
The longer the chain, the greater the number of
structural isomers

Number of Carbon Atoms Number of Isomers

4 2
5 3
6 5
7 9
8 18
9 35
10 75
12 355
15 4347