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Oil Hydrocarbon)

Oil Hydrocarbon)

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HYDROCARBONS

the term hydrocarbon to the standard chemical one; elsewhere in this text usage will vary, as it does
in the real world.

below.

In each of these compounds, and indeed in every carbon compound (except a few highly unstable
ones created only in laboratories), every carbon atom forms four bonds. Similarly, hydrogen always
forms one bond; oxygen and sulfer, two bonds; and nitrogen, three bonds. Carbon atoms like to
form bonds with each other, creating long chains and ring structures. This unique property of
carbon is responsible for the existence of literally millions of different organic compounds.
Writing the detailed structure of a simple molecule like methane is no problem, especially if one has
to do it only occasionally. If one wants to draw large molecules, however, the explicit inclusion of
every atom and every bond becomes extremely tedious. Several different types of shorthand have
therefore developed to facilitate drawing organic molecules.
One common convention is to represent all the hydrogen atoms attached to a given carbon atom by
a single H, using a subscript on the H to denote the total number of hydrogens around that atom.
The structures of methane and ethane are thus represented by CH4 and CH3CH3 respectively.
We can make other logical simplifications for longer carbon chains. The following representations
of n-pentane are equivalent: CH3CH2CH2CH2CH3 or CH3(CH2)3CH3.

In chemical terms a hydrocarbon is a compound containing only the elements carbon and hydrogen.
Petroleum and natural gas are themselves often referred to as "hydrocarbons," but that usage is
incorrect trom the chemist's point of view because those materials often contain substantial amounts
of nitrogen, sulfur, oxygen, trace metals, and other elements. In this chapter we restrict the usage of

Examples of hydrocarbons are methane, ethane, and cyclohexane, whose structures are shown

Organic Chemistry - 14

An even quicker shorthand that uses no letters at all has evolved. Each carbon atom is represented
by a point, and carbon-carbon bonds are shown as lines connecting those points. Hydrogen atoms
and bonds to hydrogen atoms are not shown at all. Because we know that each carbon atom forms
four bonds and each hydrogen atom forms one bond, simple inspection shows how mant' hydrogen
atoms each carbon atom must have. For example, n-pentane and cyclohexane are represented by the
line structures shown below.

The zigzag configuration illustrated for n-pentane is
adopted to show clearly each carbon atom.
The simplest series of hydrocarbons has linear structures;
these molecules are called n-alkanes or nparains. The
letter n stands for normal, and indicates that there is no
branching in the carbon chain. We have ahready
encountered n-pentane; the names of the other nine
simplest n-alkanes are given in the following table. Note
that the name of each compound ends in -ane, as in "alkane." The first four names are irregular, but
the prefixes denoting the number of carbon atoms in the other alkanes are derived from Greek
numbers.

Names and formulas of the ten smallest n-alkanes

Methane

CH4

CH4

Ethane

C2H6

CH3CH3

Propane

C3H8

CH3CH2CH3

Butane

C4H10

CH3 (CH2)2 CH3

Pentane

C5H12

CH3 (CH2)3 CH3

Hexane

C6H14

CH3 (CH2)4 CH3

Heptane

C7H16

CH3 (CH2)5 CH3

Octane

C8H18

CH3 (CH2)6 CH3

Nonane

C9H20

CH3 (CH2)7 CH3

Decane

C10H22

CH3 (CH2)8 CH3

Carbon atoms need not always bond together in a linear arrangement. Branching can occur, giving
rise to a vast number of possible structures.
The term methyl, which we used earlier, is the adjectival form of the word methane. In the case of 2-
methylhexane (C7H16) the basic structure is hexane; a CH3 (methyl) group is attached to the second
carbon atom. Other adjectival forms are made by dropping the -ane ending and adding yl (for
example, ethyl and propyl).
Among the most important branched hydrocarbons in organic geochemistry are the isoprenoids.
Regular isoprenoids consist of a straight chain of carbon atoms with a methyl branch on every
fourth carbon. Isoprenoids ranging in length from six to forty carbon atoms have been found in
petroleum and rocks.

We have also seen that carbon atoms can be arranged in rings. These cyclic compounds (called
naphthenes) are named by counting the number of carbon atoms in the ring and attaching the prefix
cyclo.
All the compounds mentioned above are called saturated hydrocarbons or saturates, because they
are saturated with respect to hydrogen. That is, no more hydrogen can be incorporated into the
molecule without breaking it apart.
Another important group of hydrocarbons is the unsaturates, which, in contrast, are able to
combine with additional hydrogen. Many unsaturated compounds have carbon-carbon double

Organic Chemistry - 15

bonds; these compounds are called alkenes. Examples are ethene (C2H4) , propene (C3H6), and
cyclohexene (C6H10), the structures of which are shown below. They are named in a similar manner
to the alkanes, except that the ending -ene indicates the presence of a double bond.

Because alkenes are highly reactive, they do not long persist in geologic environments. In the
laboratory they are readily converted to alkanes by the addition of hydrogen in the presence of a
catalyst. By hydrogenation ethene thus reacts to form ethane.

A variety of reactions, including hydrogenafion, converts alkenes to alkanes and cyclic compounds
during diagenesis.
Aromatics form an extremely important class of unsaturated hydrocarbons. At first glance
aromatics appear to be nothing more than cyclic alkenes containing several double bonds, but they
actually have completely different chemical properties from alkenes and are unusually stable.
Although they are unsaturated, they do not add hydrogen easily. Their stability permits aromatics to
be important constituents of oils and sediments.
Aromatics possess a system of alternating single and double bonds within a cyclic structure. A
simplified notation for drawing these molecules permits us to represent the double-bond system by a
circle within the ring. The circle indicates that the electrons in the double bonds are delocalized;
that is, they are free to move throughout the cyclic system instead of being held between two
particular carbon atoms. It is this delocalization of electrons which makes aromatic compounds
very stable.
Some aromatic molecules are very large. Polycyclic aromatic hydrocarbons having fused ring
structures are quite common. The extreme case is graphite, which is an almost-endless sheet of
aromatic rings.
The hydrocarbons we discussed so far are relatively simple molecules. Although they are very
important constituents of petroleum, these compounds are quite different trom the majority of the
organic molecules found in living organisms. Most biological molecules are larger and more

degradation of biogenic molecules. In fact, some complex hydrocarbons that are found in fossil
organic material can be related directly to individual biological precursors.

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