Hydrocarbons and Simple Alkanes
Australia's Lytton refinery in Brisbane processed 109,000 barrels of crude oil every single day in 2020, turning a thick black liquid into 50 different products.
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Q1 · Petrol, natural gas, candle wax, and butter all burn, what do you think these substances have in common at the molecular level that makes them flammable?
Q2 · Why do you think the length of a hydrocarbon molecule (e.g. short chain vs long chain) might change how it behaves, for instance whether it is a gas, liquid, or solid at room temperature?
● Know
- The general formula for alkanes: CnH(2n+2)
- The names and formulas of the first five alkanes (methane to pentane)
- How boiling point changes with chain length
● Understand
- Why alkanes are called 'saturated' hydrocarbons
- Why longer-chain alkanes have higher boiling points
- What makes alkanes a homologous series
● Can do
- Write molecular formulas for alkanes given the number of carbons
- Name alkanes from their formula
- Predict and explain the trend in boiling points
When crude oil is pumped out of the ground, it is a viscous black liquid with a strong smell, it looks nothing like the clear petrol you pump at a service station, yet both contain the same family of molecules. Crude oil is a mixture of hydrocarbonsorganic compounds containing only carbon and hydrogen atoms. It formed over 300 million years from the remains of marine microorganisms (phytoplankton and zooplankton) that died, sank to the ocean floor, and were compressed under heat and pressure deep in the Earth's crust. This process takes millions of years, making crude oil a non-renewable resource. Because it formed from ancient living organisms, it is also classified as a fossil fuel.
Crude oil is not a pure substance, it contains hundreds of different hydrocarbon molecules, ranging from methane (CH₄, 1 carbon) to asphalt-like molecules with 50+ carbons. This mixture means crude oil cannot be used directly; it must be separated by refining. The physical process that achieves this separation is fractional distillation, which exploits the fact that different-sized hydrocarbon molecules have different boiling points, directly related to chain length and the strength of intermolecular forces between molecules.
Bass Strait crude oil (produced offshore Victoria by Esso and BHP) is a light, low-sulfur crude, it contains a higher proportion of shorter-chain hydrocarbons (petrol and kerosene fractions) than heavy Middle Eastern crudes. This makes it more valuable because refiners get more high-demand products per barrel.
Australia produces about 300,000 barrels of crude oil per day domestically (mostly Bass Strait and NW Shelf), but imports roughly 90% of its total petroleum needs. Viva Energy's Geelong refinery in Victoria and Ampol's Lytton refinery in Queensland are the last two operating oil refineries in Australia.
Fractional distillation separates crude oil by exploiting differences in boiling point between different hydrocarbon fractions. The crude oil is first heated to about 400 °C in a furnace, converting most of it to vapour. The vapour enters the bottom of a tall fractionating column, which is hot at the bottom and progressively cooler towards the top. As vapours rise through the column, they cool. Each fraction condenses at the temperature corresponding to its boiling point and is collected at that height. Short-chain molecules (fewer carbons) have weaker intermolecular forces, lower boiling points, and condense high up; long-chain molecules condense lower down.
The column is not perfectly clean, each fraction is a range of hydrocarbon chain lengths, not a single compound. This is acceptable because the fractions are defined by their intended use: petrol-range hydrocarbons (5–10 carbons), kerosene-range (10–16 carbons), diesel-range (14–20 carbons). The consistency required for each application is achieved by further refining and blending after the column. The key principle is: boiling point increases with chain length, because longer chains have more surface area for intermolecular (van der Waals) forces, more energy is needed to separate them.
In a fractionating column at 200 °C and 0.5 m height: kerosene fraction (C₁₀–C₁₆, boiling point 150–250 °C) condenses and flows out. At 300 °C and 0.1 m height: diesel (C₁₄–C₂₀, boiling point 200–300 °C) condenses. At the very bottom, bitumen (C₄₀+, mp above 300 °C) flows out as a liquid residue.
Viva Energy's Geelong refinery processes about 130,000 barrels of crude oil per day through its fractionating columns, producing petrol, jet fuel, diesel, and bitumen for road paving used across Victoria and NSW. The bitumen fraction, the heaviest, highest-boiling fraction, paves approximately 20,000 km of Australian roads per year.
Each fraction from the fractionating column has a characteristic carbon chain length range, boiling point range, and set of applications. LPG (liquefied petroleum gas, 1–4 carbons): boiling point below 0 °C, stored under pressure as liquid, used for cooking gas and camping stoves. Petrol (5–10 carbons): boiling point 40–200 °C, volatile liquid, used in car engines. Kerosene (10–16 carbons): 150–250 °C, used for jet fuel (aviation turbine fuel, ATF) and heating. Diesel (14–20 carbons): 200–300 °C, higher viscosity, used in trucks, trains, and ships.
The heavier fractions, heavy fuel oil (20–70 carbons), power large ships and industrial boilers. Bitumen (70+ carbons) is the solid-like residue used in road surfacing. Carbon chain length controls viscosity, longer chains make thicker liquids, as well as flash point (minimum temperature for ignition). Petrol ignites below 0 °C (extremely flammable); diesel ignites above 55 °C (less flammable, safer for trucks). These differences are not arbitrary, they arise directly from the molecular chain lengths of each fraction.
Jet A-1 aviation fuel (kerosene fraction, C₁₀–C₁₆) has a flash point of 38 °C and freezes at −47 °C. At Qantas's Sydney airport fuel farm, jet A-1 is stored in tanks holding over 100 million litres, pumped to aircraft through underground lines. The narrow boiling point range ensures consistent fuel performance across all aircraft types.
Sydney Airport consumes about 2.5 billion litres of jet A-1 per year, Australia's largest single site of petroleum product consumption. The fuel arrives by pipeline from Ampol's Lytton refinery in Queensland, flowing 750 km in the same pipeline that supplies diesel for NSW trucks and LPG for Queensland households.
Each fraction from the fractionating column has a characteristic carbon chain range and boiling point range. has 1–4 carbons and is stored under pressure for cooking and camping stoves. Petrol has 5–10 carbons and is used in car . has 10–16 carbons and is used as jet fuel. The heaviest residue, , has 70+ carbons and is used to surface roads.
At the start of this lesson, you heard that every time you travel by car, plane, or ship, you're burning the compressed remains of microscopic sea creatures that died 300 million years ago, and that a single industrial process, fractional distillation, transforms crude oil into every liquid fuel, plastic, and lubricant we use today.
Now that you've worked through the lesson, how has your understanding of hydrocarbons and alkanes shifted? Can you now explain what crude oil actually is at the molecular level, and why different alkanes come out of the distillation column at different points?
Q1. Write the molecular formula and state the number of hydrogen atoms in hexane (6 carbons). Use the general formula CnH(2n+2).
Q2. Explain the trend in boiling points for methane, propane, and octane. Why does natural gas (mainly methane) exist as a gas at room temperature while candle wax (long chains) is a solid?
Q3. Construct a table comparing the first four alkanes (methane to butane): name, formula, number of carbons, number of hydrogens, state at room temperature, and approximate boiling point.