HYDROCARBONS

Hydrocarbons are compounds made of only the elements carbon and hydrogen
Hydrocarbons

Aliphatic

Alkanes

Aromatic

Alkenes

Alkynes

Alkanes: Saturated Hydrocarbons

1. Saturated hydrocarbons: Hydrocarbons that have no double or triple bonds.
or
Hydrocarbons that have maximum number of hydrogen atoms per carbon.
2. Alkanes are hydrocarbons that contain only single bonds.
a) Acylic alkanes contain linear and branched chains of carbon atoms. Molecular
formula is CnH2n+2
b) Cycloalkanes contain carbons joined in one or more rings. General formula is
CnH2n
Names and Molecular Formulas of Alkanes
Name

M.Formula

Name

M.Formula

Methane

CH4

Hexane

C6H14

Ethane

C2H6

Heptane

C7H16

Propane

C3H8

Octane

C8H18

Butane

C4H10

Nonane

C9H20

Pentane

C5H12

Decane

C10H20

Structural Isomerism
Isomers are different compounds with identical molecular formulas. The phenomenon is called
isomerism. Example:
C4H10
CH3CH2CH2CH3

CH3CHCH3
CH3

n-butane

isobutane

Structural or constitutional isomers are isomers that differ in the sequence of atoms bonded to each
other.
C5H12

CH3
CH3CH2CH2CH2CH3
n-pentane

CH3

CH3CHCH2CH3

CH3CCH3

isopentane

CH3
neopentane

Other example of structural isomers:

CH3CH2OH

CH3-O-CH3

M.Formula C2H6O

Number of Possible Structural Isomers of Alkanes

Name

Molecular Formula

Number of isomers

Methane

CH4

Ethane

C2H6

Propane

C3H8

Butane

C4H10

Pentane

C5H12

Hexane

C6H14

Decane

C10H22

75

Eicosane

C20H42

366,319

Classes of Carbons and Hydrogens

C
C C

C C

10 carbon

C
C C C

20carbon

30 carbon

Example:

10 10
CH3CH3
CH3CH2 C
H
0

20

10

C CH3
CH3

30

40
10

H C C

1 H

C
H C C

C
H C C
C

20 H

30 H

Example:

30 10
H
CH3CH2 C

CH3

CH3
10 20
10

C
C C C
C

40 carbon

Alkyl Groups
An alkyl group is an alkane from which a hydrogen has been removed. The symbol is
-H

CH4

CH3-

Methane
CH3CH3

Methyl
-H

CH3CH2-

Ethane

Ethyl
CH3CH2CH2-

-H
CH3CH2CH3

n-propyl

Propane

-H
CH3CHCH3
isopropyl
-H

CH3CH2CH2CH3

CH3CH2CH2CH2n-butyl

-H

n-butane

CH3CHCH2CH3
sec-butyl (secondary)
CH3
CH3CH

-H

CH3
isobtane

CH3
CH3CH
CH2-

-H

isobutyl
CH3
CH3CCH3
tert-butyl or t-butyl (tertiary)

Nomenclature of Alkanes
Common names:
isobutane
isopentane
neopentane
IUPAC names:
International Union of Pure and Applied Chemistry
Step 1: Find the parent carbon chain and add the suffix (functional group present)
C
C

C-C-C-C-C-C-C-C
C

C
=

C CC
C-C-C-C-C-C
C C
C

8 Cs

Octane

C
C C
C-C-C-C-C
C-C-C-C

If there are two chains of equal length, pick the chain with more substituent.
substituent

substituent

C
C-C-C-C-C-C-C
C

substituent

C
C-C-C-C-C-C-C
C
C

Correct

Incorrect

7 Cs and 2 substituent

7Cs and 1 substituent

Step 2: Number the atoms in the carbon chain. Give the substituent the lower number

C
C
3
C-C-C-C-C-C
1 2

4 5 6

C
C
4
C-C-C-C-C-C
6 5

3 2 1

CH3 at C2,C3 and C5

CH3 at C2, C4 and C5

Assign the lower number alphabetically to the first substituents

1 2 3 4 5 6 7

7 6 5 4 3 2 1

C-C-C-C-C-C-C
C C methyl
ethyl
C

C-C-C-C-C-C-C
C C methyl
ethyl
C

-Ethyl at C3

-Methyl at C3

-Methyl at C5

-Ethyl at C5

Correct

Incorrect

Step 3: Name and number the substituents

C-C
6

C-C-C-C-C-C-C-C
7 8
1 2 3 4 5
C
di-

for two

tri-

for three

tetra-

for four

dimethyl

identical groups

Step 4: Combine substituent names and numbers + parent + suffix

Alphabetize the name of substituents, ignoring all prefix except iso, as in isopropyl and isobutyl.
Separate numbered by commas and separate numbers from letters by hyphens.

C-C
6

C-C-C-C-C-C-C-C
7 8
1 2 3 4 5
C
Substituents names and numbers

parent

5-ethyl-2,6-dimethyl

oct

Alphabetize

8Cs

E for ethyl
M for methyl
Answer: 5-ethyl-2,6-dimethyloctane
Naming Cycloalkanes
Step 1: Find the parent cycloalkane

CH3

CH2CH3
6Cs cyclohexane

sufix
ane

an alkane

Step 2: Name and number the substituent. No number is needed to indicate the location of a
single substituent

CH3 Methylcyclohexane

For rings with more than one substituent, give the second substituent the lower
number

CH3
6
5

CH3

3 CH
3

1,3-dimethylcyclohexane
Correct

1
4

6
5 CH3

1,5-dimethylcyclohexane
Incorrect

With two different substituents, assign the lower number to the substituent
alphabetically

CH2CH3

CH2CH3

3 CH
3
1-ethyl-3-methylcyclohexane

1 CH3
3-ethyl-1-methylcyclohexane

Correct

Incorrect

Containing both a ring and a long chain carbon atoms

1
2

5
4

4 Cs
6 Cs

6 Cs

4 Cs

butylcyclohexane

1-cyclobutylhexane

Geometric Isomerism in Cycloalkanes

The lack of free rotation of single-bonded carbons in a ring produces a kind of
isomerism called geometric isomerism.
For example :
H

CH3

CH3 H

CH3 CH3
cis-1,2-dimethylcyclopropane

trans-1,2-dimethylcyclopropane

H
H
Br

H
CH3

CH3
H

Br

cis-1-bromo-3-methylcyclohexane

Source of alkanes
1. Natural gas
-methane (60%-80%)
-ethane, propane and butane
2. Petroleum
gasoline

C5H12-C12H26

kerosene

C12H26-C16H34

diesel fuel

C15H32-C18H38

Physical Properties of Alkanes

1. Alkanes from C1 to C4 are gasses
C5 to C17 are liquids
>C18 are wax-like solids

trans-1-bromo-3-methylcyclohexane

2. Alkanes are nonpolar compounds. Their characteristic known as like

dissolves like rule. Nonpolar compounds are soluble in other nonpolar
solvents. Polar compounds are generally soluble in other polar solvents.
Alkanes are soluble in organic solvents. Alkanes are insoluble in water.
3. Boiling Points (bp)
a) Alkanes have low bps compared to more polar compounds of comparable size
CH3CH2CH3

CH3C-H

CH3CH2OH

MW= 44

MW =44

MW = 46

BP= -42oC

BP=21oC

BP=79oC

Van der Wall forces

Dipole-dipole

(weak)

attraction

Hydrogen bonding (strong)

b) Bp increases as the numbers of carbons increases because of increased surface

area
CH3CH2CH2CH3
BP = 0oC

CH3CH2CH2CH2CH3
BP = 36oC

CH3CH2CH2CH2CH2CH3
BP = 69oC

Increasing surface area

Increasing bp
c) The bp of isomers decrease with branching because of decreased surface area

CH3
CH3C-CH3
CH3
BP = 10oC

CH3
CH3CHCH2CH3
BP = 30oC
Increasing surface area
Increasing bp
Increasing branching

CH3CH2CH2CH2CH3
BP = 36oC

Reactions of Alkanes
1. Combustion: is a rapid oxidation that takes place at high temperature,
converting alkanes to carbon dioxide and water.
+

CnH2n+2

CH3CH2CH3

nCO2

excess O2

5O2

flame

3CO2

(n+1)H2O

4H2O

heat

heat

2. Halogenation: is the typical substitution reaction of alkanes.

H
C
H

H
C
X

heat

X2

or
UV light

HX

(X2 =Cl2 or Br2)

CH4

Cl2

heat
or UV

CH3CH3 +

CH3CH2CH3

Cl2

heat
or UV

CH3Cl

Cl2

HCl

heat
or UV

CH3CH2CH2Cl

CH3CH2Cl

HCl

HCl

Mechanism of halogenation of alkanes

1. Chain-initiation step

Cl

Cl

2Cl

2. Chain-propargation step

Cl

H
C H
H

H-Cl

3. Chain-terminating step
Cl

H
C
H

H
C
H

Cl

Cl2

H
C H
H

H H
H C C H
H H

Cl

H
H C Cl
H

or

or