Organic

Chemistry

UNIVERSITY OF SOMALIA
Isomers
• (structural) isomers: compounds with the
same molecular formula but different structure
(arrangement of atoms)
• How about C5H12? The isomers are:

Pentane 2-methyl-butane 2,2-dimethyl propane

 Nomenclature Practice
Name this compound

CH3
H3C1 2 CH3 9 carbons = nonane
3 4 5
6
Cl 7
8
H3C9

Step #1: For a branched hydrocarbon, the longest

continuous chain of carbon atoms gives the root name
for the hydrocarbon
 Nomenclature Practice
Name this compound

CH3
9 carbons = nonane
H3C1 2 CH3
3 4 5
6 CH3 = methyl
Cl 7
8 chlorine = chloro

H3C9

Step #2: When alkane groups appear as substituents, they are named
by dropping the -ane and adding -yl.
 Nomenclature Practice
Name this compound

CH3
9 carbons = nonane
H3C1 2 CH3
3 4 5
6 CH3 = methyl
Cl 7
8 chlorine = chloro

H3C9

1 9 NOT 9 1

Step #3: The positions of substituent groups are

specified by numbering the longest chain of carbon
atoms sequentially, starting at the end closest to the
branching.
 Nomenclature Practice
Name this compound

CH3
9 carbons = nonane
H3C1 2 CH3
3 4 5
6 CH3 = methyl
Cl 7
8 chlorine = chloro

H3C9

2-chloro-3,6-dimethylnonane

Step #4: The location and name of each substituent are

followed by the root alkane name. The substituents are
listed in alphabetical order (irrespective of any prefix),
and the prefixes di-, tri-, etc. are used to indicate
multiple identical substituents.
 Naming Practice!!!

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

choose the correct ending

ene
 CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

determine the longest carbon chain with

the double bond
ene
 CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

assign numbers to each carbon

ene
 CH2 CH2 CH3
1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3

assign numbers to each carbon

ene
 CH2 CH2 CH3
1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3

attach prefix (according to # of carbons)

1-hexene
ene
 CH2 CH2 CH3
ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
determine name for side chains
1-hexene
 CH2 CH2 CH3
ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
attach name of branches alphabetically
2-ethyl-4-methyl-4-methyl-1-hexene
 CH2 CH2 CH3
ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
group similar branches
2-ethyl-4-methyl-4-methyl-1-hexene
CH3 CH CH2 CH3 CH3
propene CH3 CH CH C CH3

CH3 CH CH CH3
2,4-dimethyl-2-pentene
2-butene 2,4-dimethyl pent-2-tene
 CH3 CH3

CH2 CH C CH2 CH3 CH3 C CH CH2

CH3 CH2 CH3

a) 3,3-dimethyl-1-pentene b) same

CH3

CH3 C C CH CH CH3

CH3
c) 4,5 dimethyl-2-hexene
 Examples

5 4 3 2 1
CH3 CH2 CH2 CH CH3 parent alkane

CH3
alkyl group

2-methylpentane
 Examples

1 2 3 4
CH3 CH CH CH3
CH3 CH3
2,3-dimethylbutane

CH3
4 3 2 1
CH3 CH2 C CH3
CH3
2,2-dimethylbutane
 Examples

CH3 CH3
7 6 5 3 1
CH3 CH CH2 CH CH CH CH3
4 2
CH3 CH3

2,3,4,6-tetramethylheptane

Note: Number the chain so that the substituents get the lowest
possible numbers.
 Examples

2 1
CH2 CH3

CH3 CH CH2 CH2 CH3

3 4 5 6

3-methylhexane

Caution: Be careful to choose the longest chain as the parent alkane.

 Examples

CH2 CH3
8 7 6 5 4 3 2 1
CH3 CH2 CH2 CH2 C CH CH CH3
CH3 Cl CH3

3-chloro-4-ethyl-2,4-dimethyloctane

Note: Substituents are listed in alphabetical order.

 Draw the Compounds
• 3-ethylpentane
1 2 3 4 5
CH3 CH2 CH CH2 CH3
CH2 CH3

• 2,2,4-trimethylpentane
CH3
1 2 3 4 5
CH3 C CH2 CH2 CH3
CH3 CH3
 Skeletal structure
• A common method used by organic chemists to
simplify the drawings of larger molecules is to use a
skeletal structure (also called a line-angle structure).
In this type of structure, carbon atoms are not
symbolized with a C, but represented by each end of
a line or bend in a line. Hydrogen atoms are not
drawn if they are attached to a carbon.
• Other atoms besides carbon and hydrogen are
represented by their elemental symbols.
Draw the skeletal structures for these four
molecules:
Identify the chemical formula of
the molecule represented here:
Naming of alkenes