Classification of Organic Compounds

Organic
Compounds

Hydrocarbons

Aliphatic

Aromatic

Hydrocarbon Derivatives

Halogen
Containing

Oxygen
Containing

Nitrogen
Containing

Classification of Organic Compounds

Hydrocarbons

Aliphatic

Saturated

Unsaturated

Aromatic

Benzenes

Polycyclic
Benzene

Classification of Organic Compounds

Aliphatic

Saturated

Alkanes

Unsaturated

Alkenes

Alkynes

Alkanes
are compounds that contain only C-C
and C-H bonds
generally come from fossil fuels,
particularly natural gas and crude oil
Formula is always CnH2n+2

Structural Formulas
Alkanes are written with structural formulas that are
expanded to show each bond (Lewis Structure).
condensed to show each carbon atom and hydrogen atoms
attached to that carbon.
Expanded (Lewis)
H

Condensed

CH4 , methane

H
5

Expanded and Condensed Structures

Structural Formulas
Condensed formulas are written for expanded
structural formula by showing each carbon and the
attached hydrogen atoms.
Expanded
Condensed
H H H H

HC C C C H

H H H H

CH3CH2CH2CH3

Alkane Nomenclature

the names of all

organic compounds
stem from the names
of the alkanes

Alkane Nomenclature
Straight chain alkanes are
alkanes in which all the carbon
atoms line up in a row.
Called unbranched or normal

Alkane Nomenclature
Unbranched/ Normal Alkanes

#C

Name

#C

Name

1
2
3
4
5
6
7
8
9
10

Methane
Ethane
Propane
Butane
Pentane
Hexane
Heptane
Octane
Nonane
Decane

11
12
13
14
15
16
17
18
19
20

Undecane
Dodecane
Tridecane
Tetradecane
Pentadecane
Hexadecane
Heptadecane
Octadecane
Nonadecane
Eicosane

Alkane Nomenclature

Propane

Butane

Pentane

Condensed Structural Formula

Actually Zig-Zag Structures
All Carbons sp3 Hybridized

Heptane

Alkane Nomenclature
Name the smaller rows that
branch off of the larger rows as
if they were little independent
alkanes of their own, better
known as alkyl groups.

Alkane Nomenclature
Alkyl group: Methyl

Hexane or n-hexane

Alkyl Group Nomenclature

Unbranched Alkyl Groups

#C

Name

#C

Name

1
2
3
4
5
6
7
8
9
10

Methyl
Ethyl
Propyl
Butyl
Pentyl
Hexyl
Heptyl
Octyl
Nonyl
Decyl

11
12
13
14
15
16
17
18
19
20

Undecyl
Dodecyl
Tridecyl
Tetradecyl
Pentadecyl
Hexadecyl
Heptadecyl
Octadecyl
Nonadecyl
Eicosyl

Alkane Nomenclature

The carbons in an alkane

are sometimes classified
by how many other
carbon atoms are stuck
to them.

Alkane Nomenclature
Classified by the connection site
a carbon at the end of a chain (primary alkyl
group)
a carbon in the middle of a chain (secondary alkyl
group)

16

Alkane Nomenclature
Classified by the connection site
a carbon with three carbons attached to it (tertiary alkyl
group)
a quaternary (4) carbon atom has four other carbon
atoms bonded to it.

17

Alkane Nomenclature

Alkane Nomenclature

butyl group or n-butyl

Alkane Nomenclature

sec-butyl group

Alkane Nomenclature

tert-butyl group

Alkane Nomenclature
To name alkanes, we use the
system thats approved by
the International Union of
Pure and Applied Chemistry
(IUPAC) for just this
purpose.

Alkane Nomenclature
To name alkanes, we use the
system thats approved by
the International Union of
Pure and Applied Chemistry
(IUPAC) for just this
purpose.

Alkane Nomenclature: Rule 1

The root name for an alkane is based on
the longest unbroken chain of carbon
atoms (called the parent chain).
Derivative of heptane

Alkane Nomenclature: Rule 1a

When there are two longest

chains of equal length, use
the chain with the greater
number of substituents as
the main chain.

CH3

CH3CHCH2
CHCHCH2CH3
CH3 CHCH3
CH3

Which is correct?

Correct, 7-Carbon chain w/ 4

substituents

Alkane Nomenclature: Rule 2

Assign numbers to each of the carbon atoms
in this chain, beginning with the side thats
nearest the first point of branching.

Correct numbering

Alkane Nomenclature: Rule 3

Identify the names of the substituent groups
and number them according to their position
on the chain.
4-ethyl

3-methyl

Alkane Nomenclature: Rule 4

Write the names of the substituents
alphabetically, followed by the name of the
parent alkane.

4-ethyl-3-methylheptane

Another example!

2,3-dimethylhexane

More Problems!
Problem 1: Write the name of the compound
here.

Problem 2: Draw the 2,3,4-trimethylheptane

molecule.

More Problems!
Problem 3: Write the name of the compound.

More Problems!
If the numbers turn out the same way
numbering it in both directions, the correct way
to number it is by putting the alphabetically
first substituent at the position with the lowest
number.

Correct
numbering

More Problems!
Problem 3: Write the name of the compound.

3-ethyl-4-methylhexane

CH3

CH3CHCH2
CHCHCH2CH3
CH

CHCH3
CH3

Which is correct?

Correct, 7-Carbon chain w/ 4

substituents

CH3

CH3CHCH2
CHCHCH2CH3
CH3 CHCH3
CH3

Derivative of heptane

3-ethyl-2,4,5-trimethylheptane

More Problems
Give the structures:
a. 4-isopropyloctane
b. 5-tert-butyldecane.

4-isopropyloctane

5-tert-butyldecane

Haloalkanes
Haloalkanes can be named just like
alkanes, with the halogen atom
treated as a substituent. Halogen
substituents are named fluoro-,
chloro-, bromo-, and iodo-.
When more than one halogen is
present in the parent chain, they must
be named alphabetically.

Haloalkanes
2-bromobutane

1,2-difluoropropane

Complex Substituents
Complex alkyl groups are named by
a systematic method using the
longest alkyl chain as the base alkyl
group.
The base alkyl group is numbered
beginning with the carbon atom
(the head carbon) bonded to the
main chain.

Complex Substituents
The substituents on the base alkyl group are listed with
appropriate numbers, and parentheses are used to set
off the name of the complex alkyl group.

A (1-ethyl-2-methylpropyl)
group
A propyl
group

Complex Substituents
A propyl
group

3-ethyl-5-(1-ethyl-2-methylpropyl)nonane

5-(1,2,2-trimethylpropyl)nonane