11.1 - Hydrocarbons & Homologous Series

Hydrocarbons and homologous series

• Organic chemistry is the chemistry of compounds that contain carbon.
• A hydrocarbon is a compound made up of hydrogen and carbon only.
  • Methane (CH₄) is a hydrocarbon. Ethanol is not, because it contains oxygen.

Why there are so many carbon compounds

• A carbon atom forms four covalent bonds, and it bonds readily to other carbon atoms.
• Carbon atoms join end to end into chains (short or long) and into rings.
• Each carbon uses its remaining bonds to join to hydrogen atoms or atoms of other elements.

Homologous series

• A homologous series is a family of similar compounds.
• Members of the same homologous series share:
  • The same general formula.
  • Each member differs from the next by a CH₂ unit.
  • A gradual change in physical properties (melting and boiling points rise as molecules get bigger, because larger molecules have stronger intermolecular forces).
  • Similar chemical properties (they react in similar ways).
  • The same functional group.

Functional groups

• A functional group is an atom or group of atoms in a molecule that determines how it reacts.
• Every member of a homologous series has the same functional group, so they all react similarly.
  • Alkenes have a carbon-carbon double bond (C=C). Alcohols have an -OH group.

Alkanes

• Every bond in an alkane is a single bond, and an alkane has no functional group.
• Because they lack a functional group, alkanes are much less reactive than other organic families. They burn readily but take part in few other reactions.

The alkanes

• Alkanes are the simplest homologous series of hydrocarbons.
• Every carbon-carbon bond is a single bond, and all other bonds are to hydrogen atoms.
• An alkane holds as many hydrogen atoms as its carbon framework can, making it saturated.

The first four alkanes

Each alkane has one more carbon atom and two more hydrogen atoms than the one before it (the CH₂ step).

Ways to write an alkane

• Molecular formula - Shows the actual number of atoms of each element in a molecule (e.g. propane is C₃H₈).
• Structural formula - Shows the arrangement of atoms along the chain without drawing every bond (e.g. propane is CH₃CH₂CH₃).
• Displayed formula - Shows every atom and every covalent bond as a line.

When drawing a displayed formula, check that every carbon atom has four bonds and every hydrogen atom has one.

Recognising an alkane

• A name ending in -ane.
• A structure containing only carbon and hydrogen with single C-C bonds only.

General formulae of homologous series

• A general formula is an algebraic formula describing every member of a homologous series.
• The letter n represents the number of carbon atoms in the molecule.

The four general formulae to learn

• Alkanes and alkenes are hydrocarbons, so their formulae contain only carbon and hydrogen.
• Alcohols and carboxylic acids contain oxygen, written in their functional group at the end.

Using a general formula

Substitute the number of carbon atoms for n:

• Alkane with 3 carbons: n = 3, hydrogens = (2 × 3) + 2 = 8, giving C₃H₈.
• Alkene with 3 carbons: n = 3, hydrogens = 2 × 3 = 6, giving C₃H₆.

For formulae containing functional groups:

• Alcohol - n is the total number of carbons. For n = 2: hydrogens = (2 × 2) + 1 = 5 in the chain, giving C₂H₅OH (2 carbons total).
• Carboxylic acid - The -COOH group already contains one carbon, so n counts the remaining carbons. For ethanoic acid (2 carbons total), n = 1: hydrogens = (2 × 1) + 1 = 3, giving CH₃COOH.

Identifying the series from a formula

Compare a molecular formula to the general formulae:

• C₅H₁₂ fits C_nH_2n+2 ((2 × 5) + 2 = 12), so it is an alkane.
• C₄H₈ fits C_nH_2n (2 × 4 = 8), so it is an alkene.

The alkenes

• Alkenes are hydrocarbons that contain a carbon-carbon double bond (C=C).
• Every other bond in the molecule is a single bond.
• The double bond is the alkenes' functional group.

Why alkenes are unsaturated

• Because two bonds are shared between two carbons in the C=C double bond, each of those carbons has one fewer bond available for hydrogen.
• An alkene therefore has two fewer hydrogen atoms than the alkane with the same number of carbons (e.g. ethane is C₂H₆; ethene is C₂H₄).
• Compounds containing double bonds that could hold more hydrogen atoms are unsaturated.

The first three alkenes

There is no alkene with one carbon atom, because a C=C double bond requires at least two carbons.

Two forms of butene

• With an unbranched chain of four carbon atoms, butene (C₄H₈) exists in two structural forms:
  1. In but-1-ene, the double bond is between the first and second carbons.
  2. In but-2-ene, the double bond is between the second and third carbons.
• The number indicates the position of the double bond, counting from the end that gives the lowest number.

Recognising an alkene

• A name ending in -ene.
• A structure containing a carbon-carbon double bond (C=C).