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Chemistry LibreTexts

12.2: Structures and Names of Alkanes

Skills to Develop

  • To identify and name simple (straight-chain) alkanes given formulas and write formulas for straight-chain alkanes given their names.

We begin our study of organic chemistry with the hydrocarbons, the simplest organic compounds, which are composed of carbon and hydrogen atoms only. As we noted, there are several different kinds of hydrocarbons. They are distinguished by the types of bonding between carbon atoms and the properties that result from that bonding. Hydrocarbons with only carbon-to-carbon single bonds (C–C) and existing as a continuous chain of carbon atoms also bonded to hydrogen atoms are called alkanes (or saturated hydrocarbons). Saturated, in this case, means that each carbon atom is bonded to four other atoms (hydrogen or carbon)—the most possible; there are no double or triple bonds in the molecules.

The word saturated has the same meaning for hydrocarbons as it does for the dietary fats and oils: the molecule has no carbon-to-carbon double bonds (C=C).

We previously introduced the three simplest alkanes—methane (CH4), ethane (C2H6), and propane (C3H8) and they are shown again in Figure \(\PageIndex{1}\).

12.1.jpg

Figure \(\PageIndex{1}\): The Three Simplest Alkanes

The flat representations shown do not accurately portray bond angles or molecular geometry. Methane has a tetrahedral shape that chemists often portray with wedges indicating bonds coming out toward you and dashed lines indicating bonds that go back away from you. An ordinary solid line indicates a bond in the plane of the page. Recall that the VSEPR theory correctly predicts a tetrahedral shape for the methane molecule (Figure \(\PageIndex{2}\)). 

12.2.jpg

Figure \(\PageIndex{2}\): The Tetrahedral Methane Molecule

Methane (CH4), ethane (C2H6), and propane (C3H8) are the beginning of a series of compounds in which any two members in a sequence differ by one carbon atom and two hydrogen atoms—namely, a CH2 unit. The first 10 members of this series are given in Table \(\PageIndex{1}\).

Table \(\PageIndex{1}\): The First 10 Straight-Chain Alkanes
Name Molecular Formula (CnH2n + 2) Condensed Structural Formula Number of Possible Isomers
methane CH4 CH4
ethane C2H6 CH3CH3
propane C3H8 CH3CH2CH3
butane C4H10 CH3CH2CH2CH3 2
pentane C5H12 CH3CH2CH2CH2CH3 3
hexane C6H14 CH3CH2CH2CH2CH2CH3 5
heptane C7H16 CH3CH2CH2CH2CH2CH2CH3 9
octane C8H18 CH3CH2CH2CH2CH2CH2CH2CH3 18
nonane C9H20 CH3CH2CH2CH2CH2CH2CH2CH2CH3 35
decane C10H22 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 75

Consider the series in Figure \(\PageIndex{3}\). The sequence starts with C3H8, and a CH2 unit is added in each step moving up the series. Any family of compounds in which adjacent members differ from each other by a definite factor (here a CH2 group) is called a homologous series. The members of such a series, called homologs, have properties that vary in a regular and predictable manner. The principle of homology gives organization to organic chemistry in much the same way that the periodic table gives organization to inorganic chemistry. Instead of a bewildering array of individual carbon compounds, we can study a few members of a homologous series and from them deduce some of the properties of other compounds in the series.

12.3.jpg

Figure \(\PageIndex{3}\): Members of a Homologous Series. Each succeeding formula incorporates one carbon atom and two hydrogen atoms more than the previous formula.

The principle of homology allows us to write a general formula for alkanes: CnH2n + 2. Using this formula, we can write a molecular formula for any alkane with a given number of carbon atoms. For example, an alkane with eight carbon atoms has the molecular formula C8H(2 × 8) + 2 = C8H18.

Key Takeaway

  • Simple alkanes exist as a homologous series, in which adjacent members differ by a CH2 unit.