Alkane reactions and cracking

Key idea: Alkanes burn in oxygen and undergo chlorine substitution in UV light. Cracking uses heat and a catalyst to turn large alkane molecules into smaller alkanes and alkenes.

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Methane can burn, a chlorine atom can replace one of its hydrogen atoms, and a refinery can turn larger hydrocarbons into smaller ones. These are chemical changes: the atoms are rearranged, but none disappear. This lesson helps you distinguish the reactions and use atom conservation to complete cracking equations.

Start with hydrocarbon structures: an alkane has only single carbon–carbon bonds, while an alkene has a carbon–carbon double bond. You also need to balance an equation without changing the formulae of substances. The crude-oil lesson explains the separate physical process of fractional distillation.

Alkanes: combustion and substitution

Alkanes contain only strong C-C and C-H single bonds. They do not react readily with acids, alkalis or most other reagents under ordinary laboratory conditions. Combustion and substitution are two important reactions to learn.

Combustion. Alkanes burn in plenty of oxygen to form carbon dioxide and water, which is why they are good fuels:

C₃H₈ + 5O₂ → 3CO₂ + 4H₂O

Substitution by chlorine. In ultraviolet (UV) light, such as sunlight, methane reacts with chlorine. One chlorine atom takes the place of one hydrogen atom:

CH₄ + Cl₂ → (UV light) CH₃Cl + HCl

The products are chloromethane and hydrogen chloride. This is a substitution reaction: one atom is replaced by another. UV light starts this reaction under the conditions studied here. Further substitution can replace more hydrogen atoms; the equation shows the first substitution.

Methane and chloromethane

Methane is a carbon with four hydrogens. Chloromethane is a carbon with three hydrogens and one chlorine. The carbon still has four single bonds.

Scroll across the figure to read all labels.

Displayed structures of methane and chloromethane; in chloromethane one hydrogen has been replaced by chlorineDisplayed structures of methane and chloromethane; in chloromethane one hydrogen has been replaced by chlorine
Substitution swaps one hydrogen for one chlorine. The carbon keeps four single bonds, and the removed hydrogen leaves as hydrogen chloride.
View figure data
Atoms bonded to the carbon
MoleculeMolecular formulaAtoms bonded to carbon
methaneCH₄4 H
chloromethaneCH₃Cl3 H and 1 Cl

Check your understanding 1 Track what is replaced in substitution

For the first reaction of methane with chlorine, choose the condition and what happens to a hydrogen atom. Then identify the second product alongside chloromethane.

Reaction condition
What happens to one methane hydrogen?
Second product

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CH₄ + Cl₂ → (UV light) CH₃Cl + HCl. One chlorine replaces one methane hydrogen; the other chlorine forms hydrogen chloride with the removed hydrogen. All atoms balance, and carbon still has four single bonds.

Check your understanding 2 Balance methane’s complete combustion

For one methane molecule, complete the coefficients in CH₄ + ? O₂ → ? CO₂ + ? H₂O. The oxygen supply is plentiful.

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CH₄ + 2O₂ → CO₂ + 2H₂O. Carbon and hydrogen enter carbon dioxide and water. The next activity asks for the full equation and comparison with substitution.

Check your understanding 3 Burning methane

Write a balanced equation for methane burning in plenty of oxygen. Explain how the products differ from those in its first substitution with chlorine.

Work on paper or in the optional notes. Compare the full balanced combustion equation with both first-substitution products and how their atoms are rearranged.

Show answer

CH₄ + 2O₂ → CO₂ + 2H₂O. Complete combustion forms carbon dioxide and water; all carbon and hydrogen enter these products. The first chlorine substitution instead replaces one hydrogen and forms chloromethane and hydrogen chloride.

Cracking changes molecules

Cracking breaks large alkane molecules into smaller ones. The large molecules are heated and passed over a catalyst. The products are smaller alkanes and alkenes, and sometimes hydrogen:

C₁₀H₂₂ → C₈H₁₈ + C₂H₄ C₂H₆ → C₂H₄ + H₂

Every carbon and hydrogen atom in the large molecule ends up in a product, so the atoms balance on each side.

Cracking redistributes the atomsHigh temperature and a catalyst are used in catalytic cracking. In the first model equation, C10H22 forms C8H18 plus C2H4, retaining ten carbon and twenty-two hydrogen atoms. In a separate example, C2H6 forms C2H4 plus H2, retaining two carbon and six hydrogen atoms. These examples do not specify the full mixture from an industrial cracker.High temperature + catalystC₁₀H₂₂C₈H₁₈+C₂H₄Larger alkaneSmaller alkaneAlkeneAtom totals on each side: 10 C and 22 HC₂H₆C₂H₄+H₂AlkaneAlkeneHydrogenAtom totals on each side: 2 C and 6 H
Cracking redistributes the atomsHigh temperature and a catalyst are used in catalytic cracking. In the first model equation, C10H22 forms C8H18 plus C2H4, retaining ten carbon and twenty-two hydrogen atoms. In a separate example, C2H6 forms C2H4 plus H2, retaining two carbon and six hydrogen atoms. These examples do not specify the full mixture from an industrial cracker.High temperature + catalystC₁₀H₂₂Larger alkaneC₈H₁₈+C₂H₄Smaller alkaneAlkeneAtom totals on each side: 10 C and 22 HC₂H₆AlkaneC₂H₄+H₂AlkeneHydrogenAtom totals on each side: 2 C and 6 H
Two model equations show different possible products. The first gives a smaller alkane and an alkene; the second gives an alkene and hydrogen. Both conserve carbon and hydrogen atoms.

Crude oil gives more large molecules than people need, and fewer small molecules than people need. These illustrative shares compare supply and demand for the same total amount:

FractionsShare of crude oil supplied / %Share of demand / %
small molecules (refinery gas, petrol, naphtha)2545
medium molecules (kerosene, diesel)3535
large molecules (fuel oil, bitumen)4020

Cracking turns some of the surplus large molecules into the smaller molecules that are in demand. It is also how alkenes such as ethene are manufactured, and ethene is the starting material for many plastics. This is why cracking is essential to a refinery.

Check your understanding 4 Read the supply and demand before choosing the process

Use the illustrative supply/demand table above. Find demand minus supply for small-molecule fractions, and supply minus demand for large-molecule fractions. Enter both differences in percentage points, then choose the process that can change large molecules into smaller hydrocarbons.

Unit: percentage points
Unit: percentage points
Process that can change large molecules into smaller hydrocarbons

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Small fractions have a shortfall of 20 percentage points; large fractions have a surplus of 20 percentage points. Cracking can turn some surplus large molecules into smaller ones, including useful alkenes. The table describes shares of a common total; it does not specify one exact cracking equation or industrial product mixture.

Complete a cracking equation

In a model equation, cracking gives an alkene and one other product. Use the supplied formulae to account for the carbon and hydrogen atoms. An atom balance checks the proposed products; it does not predict the full product mixture from an industrial cracker.

Guided practice 1

Find the missing alkene

About 5 min

Problem

In one possible reaction, an alkane cracks to form C₆H₁₄ and one alkene Y: C₉H₂₀ → C₆H₁₄ + Y. First find the carbon and hydrogen counts in Y and name the alkene. Construct and check the complete equation in the next activity.

Account for both elements

Name of Y

Hints

Hint 1

Carbon atoms

There are nine carbon atoms before the reaction. Six are in the known product.
Hint 2

Hydrogen atoms

Do the same subtraction for hydrogen. Check that the formula fits an alkene.
Show solution step by step
  1. Account for carbon

    Method

    Three carbon atoms remain for Y.

    Reason

    Each atom must appear in one of the products.

    Working

    Answer

    9 − 6 = 3 carbon atoms.
  2. Account for hydrogen

    Method

    Six hydrogen atoms remain for Y.

    Reason

    The known product uses fourteen of the twenty hydrogen atoms.

    Working

    Answer

    20 − 14 = 6 hydrogen atoms, so Y is C₃H₆: propene.
  3. Check both elements

    Method

    The equation balances.

    Reason

    C₃H₆ fits the formula of the three-carbon alkene.

    Working

    Answer

    C₉H₂₀ → C₆H₁₄ + C₃H₆. Carbon: 9 = 6 + 3. Hydrogen: 20 = 14 + 6.

Check your understanding 5 Construct and check the complete cracking equation

For C₉H₂₀ → C₆H₁₄ + Y, construct the complete equation with Y’s formula. Name Y and show that both atom totals balance. Work on paper or in optional notes.

Show answer

C₉H₂₀ → C₆H₁₄ + C₃H₆. Y is propene. Carbon: 9 = 6 + 3. Hydrogen: 20 = 14 + 6. Both elements balance and the remaining C₃H₆ fits the alkene specified. An atom balance validates this proposed equation; it does not identify the full industrial cracking mixture.

Check your understanding 6 Find the second missing product independently

For the model equation C₁₂H₂₆ → C₁₀H₂₂ + ?, find the carbon and hydrogen counts in the missing molecule and name it.

Product name

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The missing molecule is ethene, C₂H₄. Now write the complete equation, check both totals and explain a use of the product.

Check your understanding 7 Crack a C₁₂ alkane

Complete the model cracking equation C₁₂H₂₆ → C₁₀H₂₂ + ?. Name the missing product, check both atom totals and explain one use of the product.

Work on paper or in the optional notes. Compare the full equation, both atom totals and how ethene can be used to make a plastic.

Show answer

The atoms left over are 12-10 = 2 C and 26-22 = 4 H, so the product is ethene, C₂H₄. The equation is C₁₂H₂₆ → C₁₀H₂₂ + C₂H₄: 12 C and 26 H on each side. Ethene makes plastics such as poly(ethene).

Distillation or cracking?

A learner says: “The refinery needs more small molecules, so it should make its fractionating column cooler to break the large molecules.” Cooling can condense a vapour, but it does not break hydrocarbon molecules into smaller ones. Fractional distillation separates existing molecules; cracking changes them.

Check your understanding 8 Correct the refinery’s proposed solution

A refinery needs more small molecules than the crude oil supplies. A learner suggests cooling the fractionating column more to break the large molecules. Explain the effect of cooling, the process needed to change the molecules and why that helps the refinery. Work on paper or in optional notes.

Show answer

Cooling condenses vapour and can affect where existing fractions are collected, but does not break hydrocarbon molecules into smaller ones. Fractional distillation is physical separation by boiling range. Cracking uses heat and a catalyst to break large alkane molecules into smaller alkanes and alkenes. It can use surplus large fractions to supply more small molecules, and its alkenes provide feedstock for plastics. Every atom remains in a product; exact products depend on the reaction, not on the supply table alone.

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