An infinite variety of compounds can be assembled from only carbon and hydrogen

atoms. Such hydrocarbons are the simplest organic compounds, but they are also of
prime economic importance because they include the constituents of petroleum and
natural gas.

Propane, butane, and isobutane are all hydrocarbons with only single covalent bonds
between carbon atoms. These hydrocarbons that lack double bonds, triple bonds, or
ring structures make up the class called alkanes. See Table 1.

As the number of carbon atoms increases, so does the number of ways that they can be
connected to form different isomers. You should realize that isomers are defined by the
pattern of bonding between the carbons.

The two molecules in Figure 1 are not different isomers; they are both butane. Despite
the crooked carbon chain of the molecule on the right, it still has the same condensed
structural formula, as shown in Figure 2.

Figure 1. Both molecules are the same isomer of butane.

 Figure 2. The condensed structural
formula of butane.

An alkene is a hydrocarbon with at least one double bond between carbons. The
simplest alkene is ethylene, C 2H 4. See Figure 3.

Figure 3. Ethylene—an alkene.

As is the case with the alkanes, each carbon atom in an alkene has precisely four
bonds to fill its valence orbitals with eight electrons.

Another simple alkene is propene, C 3H 6. In Figure 4, propene demonstrates that

alkenes can (and usually do) contain single bonds between some carbons. The
existence of any double bond between carbons is the defining character.

Figure 4. Propene—one double and one single bond.

A hydrocarbon with a triple bond between carbons is an alkyne, and the simplest
compound in this class is acetylene, C 2H 2, as shown in Figure 5.

Figure 5. Acetylene—an alkyne.

Once again, each carbon has exactly four bonds. Of course, the triple bond between
carbons allows each carbon to bond to only one more atom. In acetylene, the single
bond is to hydrogen, but in other alkynes, the single bond is to another carbon. Table 2
compares three hydrocarbons that contain the same number of carbon atoms.

IUPAC retains these common, nonsystematic names: *Ethylene is the nonsystematic

name for ethene; **acetylene is the nonsystematic name for ethyne. These common
names are generally accepted by IUPAC.

Look at the third column of the chart and appreciate the diminishing hydrogen content of
the compounds as the number of carbon‐carbon bonds increases. Organic compounds
with multiple carbon‐carbon bonds readily react with hydrogen gas.

The hydrogenation reaction is possible only for compounds with double or triple bonds,
and such compounds are said to be unsaturated hydrocarbons.The addition of the
hydrogen to the carbon atoms that were double‐ or triple‐bonded converts the
unsaturated compound to a saturated hydrocarbonwith only single bonds.

It is possible for long chains of carbons to loop around and form a closed ring structure.
If you take the linear isomer of hexane in Figure 6 and delete the two hydrogens on the
ends, the chain can form a hexagonal structure, as shown in Figure 7.

Figure 6. Hexane.
Figure 7. Cyclohexane.

Cyclohexane contains only single bonds and is representative of the simplest type of
cyclic hydrocarbons.

A ring structure may possess double bonds, as in the following portrayal of the well‐
known hydrocarbon benzene, which has the composition C 6H 6. See Figure 8.

Figure 8. Benzene.

The two representations of the benzene ring differ in the location of the three double
bonds. The arrows between the structures represent hypothetical transitions between
the two possible configurations. Only one variety of benzene exists with all six carbon‐
carbon bonds having the same length and strength, so it seems best to regard the six
extra electrons of the double bonds as being delocalized over the entire ring structure.
Substances with benzene‐like rings are called aromaticcompounds.

 Show the three isomers of pentane as condensed structural formulas.

 Write a balanced molecular reaction for the hydrogenation of acetylene to a
saturated alkane. How many liters of hydrogen gas are needed to react
completely with 100 liters of acetylene?