HYDROCARBON

Hydrocarbon - an organic compound consisting entirely of hydrogen and carbon.

With relation to chemical terminology, aromatic hydrocarbons or arenes, alkanes, alkenes and alkyne-
based compounds composed entirely of carbon or hydrogen are referred to as "pure" hydrocarbons.
Other hydrocarbons with bonded compounds or impurities of sulphur or nitrogen, are referred to as
"impure".

Hydrocarbons are referred to as consisting of a "backbone" or "skeleton" composed entirely of carbon

and hydrogen and other bonded compounds, and lack a functional group that generally facilitates
combustion without adverse effects. The majority of hydrocarbons found naturally occur in crude oil.

TYPES OF HYDROCARBONS
The classifications for hydrocarbons defined by IUPAC nomenclature of organic chemistry are as follows:

Saturated hydrocarbons (alkanes) or acyclic alkanes

The most simple of the hydrocarbon species and are composed entirely of single bonds and are
saturated with hydrogen; they are the basis of petroleum fuels and are either found as linear or
branched species of unlimited number. The general formula: CnH2n+2 (assuming non-cyclic
structures).

Unsaturated hydrocarbons have one or more double or triple bonds between carbon atoms.
Those with one or more double bonds are called alkenes, with the formula CnH2n (assuming
non-cyclic structures). Those containing triple bonds are called alkynes, with general formula
CnH2n-2.

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Cycloalkanes are hydrocarbons containing one or more carbon rings to which hydrogen atoms
are attached. The general formula for a saturated hydrocarbon containing one ring is CnH2n.

Aromatic hydrocarbons, also known as arenes, are hydrocarbons that have at least one aromatic
ring.

CH3 CH2CH3

benzene methylbenzene ethylbenzene

Hydrocarbons can be gases (e.g. methane and propane), liquids (e.g. hexane and benzene), waxes or low
melting solids (e.g. paraffin wax and naphthalene) or polymers (e.g. polyethylene, polypropylene and
polystyrene).

In simple chemistry, as per valence bond theory, the carbon atom must follow the "4-hydrogen rule",
which states that the maximum number of atoms available to bond with carbon is equal to the number
of electrons that are attracted into the outer shell of carbon. In terms of shells, carbon consists of an
incomplete outer shell, which comprises 4 electrons, and thus has 4 electrons available for covalent or
dative bonding.
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Alkane Homolog

Types of Carbon
primary (1°) carbon : Carbon bonded to one carbon

C C

secondary (2°) carbon: Carbon bonded to two carbon

C
C C

tertiary (3°) carbon: Carbon bonded to three carbon

C
C C
C
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quaternary (4°) carbon: Carbon bonded to four carbon

C
C C C
C

Type of Hydrogen
H - primary (1°), secondary (2°) & tertiary (3°)

Primary (1°) hydrogen: Hydrogen bonded to primary carbon

Secondary (2°) hydrogen: Hydrogen bonded to secondary carbon

Tertiary (3°) hydrogen: Hydrogen bonded to tertiary carbon

Examples:
1o
1o H
1o
H 1o
1o
1o
H C1o H o
H C1o H o 2
o 1

2
o 1 Ho H H
Ho o H H 1 2o
1 3 2o Ho C C4o C C H o
Ho C C C C H o 1 1
1 1 Ho H2o H o
Ho Ho Ho H o 1 1
o 1
1
1 3 2 H C H
H 1o 4
 Alkyl Groups
- removing one hydrogen atom from an alkane
- or substituent groups
- Name: replace -ane ending of alkane with -yl ending

Draw structure for isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl and neopentyl.

Structural Isomerism
Isomers are different compounds with identical molecular formulas. Structural or constitutional isomers
are isomers that differ in the sequence of atoms bonded to each other.

Example:
Isomers for butane (C4H10)

CH3CH2CH2CH3 CH3
CH3CHCH3
n-butane Isobutene
(2-methylpropane)

Draw all possible isomer structures for pentane (C5H12) and hexane (C6H14).
Other example of structural isomers:

C2H6O

CH3CH2OH CH3-O-CH3
ethanol dimethylether
(methoxymethane)

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Alkene Substituents

Cis-Trans Isomerism
Cis, trans nomenclature only works for disubstituted double bonds

Cis : Similar groups on same side of double bond

Trans : Similar groups on opposite sides of double bond

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IUPAC NOMENCLATURE
(International Union of Pure and Applied Chemistry)

STEP 1: Determine the main chain

• Find the longest continuous chain of carbon atoms, and name it.
• Use the chain with greater number of substituents as the main chain.
• Substituents can be an alkyl groups, hydroxyl groups (-OH), halogen (-Cl,-Br,-I,-F), phenyl groups
etc.

STEP 2 & 3 : Numbering the Main Chain and naming the substituent groups
• number the longest chain, start with the end of the chain nearest to a substituent
• substituted carbons always get the lowest possible number

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STEP 4: Organizing multiple groups
• when two or more substituents are present, list them in alphabetical order.
• when two or more of the same alkyl groups or other substituent) are present, use the prefixes
di-, tri-, tetra-, hexa- etc.
• follow the alphabet of the alkyl groups, NOT the prefixes di-, tri-, tetra- (IGNORE alphabet of the
prefixes)
• When both directions lead to the same lowest number for one of the substituents, choose the
direction that gives the lowest possible number to the remaining substituents.
• If the same number is obtained in both directions, follow the alphabet of the substituent.

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How to give number to the main chain…

How to arrange the substituents…

Examples:

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Compound with complex substituent group:

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Name the following compounds using IUPAC system:

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Nomenclature of Cycloalkane
 no number is needed for a single substituent on a ring
 may be cycloalkyl attachment to chain.
 if more than one substituent, arrange in alphabetical order
 give number to the carbon of the ring
 choose the “best” combination of numbers
 If the branch has a branch, number the carbons from the point of attachment.
 Name the branch off the branch using a locator number.
 Parentheses are used around the complex branch name.

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