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Chapter 22: Hydrocarbon Compounds

Lesson 22.1: Hydrocarbons
- Fewer than 200 years ago, it was thought that only living organisms could synthesize the carbon
compounds found in their cells. So, these compounds were classified as organic compounds, and
the study of these compounds was known as organic chemistry.
- A German chemist, Friedrich Wohler (1800-1882), refuted this idea in 1828. He was able to use
inorganic substances to synthesize urea an organic compound found in urine.
- A hydrocarbon is an organic compound that contains only carbon and hydrogen.
- Methane CH4 is the major component of natural gas. It is some-times called marsh gas because
it is formed by the action of bacteria on decaying plants in swamps and other marshy areas.

- Because carbon has four valence electrons, a carbon atom always forms four covalent bonds.

- The ability of carbon to form stable carbon-carbon bonds is one reason that carbon can form so
many different compounds.

- Hydrocarbons are nonpolar molecules.

- The attractions between nonpolar molecules are weak van der Waals forces. So hydrocarbons
with low molar masses tend to be gases or liquids that boil at a low temperature.
- An alkane (CnH2n+2) is a hydrocarbon in which there are only single covalent bonds.
- The carbon atoms in an alkane can be arranged in a straight chain or in a chain that has branches.
- Ethane C2H6 is the simplest straight-chain alkane.

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- The straight-chain alkanes are an example of a homologous series.
- A group of compounds forms a homologous series if there is a constant increment of change in
molecular structure from one compound in the series to the next.

- The boiling points of the straight-chain alkanes increase as the number of carbons in the chain
increase. The melting points increase in a similar way.

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- An atom or group of atoms that can take the place of a hydrogen atom on a parent hydrocarbon
molecule is called a substituent.
- The longest continuous carbon chain of a branched-chain hydrocarbon is called the parent
alkane.
- All other carbon atoms or groups of carbon atoms are regarded as substituents.

- A hydrocarbon substituent that is derived from an alkane is called an alkyl group (CnH2n+1).

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- Alkyl groups are named by removing the -ane ending from the parent hydrocarbon name and
adding -yl.
- The three smallest alkyl groups are the methyl group (-CH3) the ethyl group (-CH2CH3)
and the propyl group(-CH2CH2CH3).
- When a substituent alkyl group is attached to a straight-chain hydrocarbon, branches are formed.
- An alkane with one or more alkyl groups is called a branched-chain alkane.
- If the carbon in question has only one carbon attached to it, then the carbon is a primary carbon.
- If two carbons are attached to the carbon in question, the carbon is a secondary carbon.
- If three carbons, a tertiary carbon; and if four carbons, a quaternary carbon.

- Isooctane is the standard for determining octane ratings of the mixtures of hydrocarbons that
make up gasoline.
- A gasoline's octane rating is a measure of its ability to prevent engine knock, which is the sound
an internal combustion engine makes when gasoline ignites too soon. Knocking reduces a
vehicle's performance and can eventually lead to engine damage.

Naming Branched-Chain Alkanes

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- To reconstruct the structural formula:

1. First, find the root word (ending in -ane) in the hydrocarbon name.
2. Then, draw the longest carbon chain to create the parent hydrocarbon, and number the
carbons on the chain.
3. Next, identify the substituent groups in the hydrocarbon name. Attach the substituents to the
numbered parent chain at the proper positions.
4. Complete the structural formula by adding hydrogens as needed

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