Alkenes
Alkenes: unsaturated hydrocarbons—cracking, bromine water test, and key addition reactions (hydrogenation, hydration, polymerisation).
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The core idea
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Learning objectives
- describe the alkenes as a homologous series of unsaturated hydrocarbons with the general formula CnH2n
- draw the structures of branched and unbranched alkenes, C2 to C4, and name the unbranched alkenes ethene to butene
- describe the manufacture of alkenes and hydrogen by cracking hydrocarbons and recognise that cracking is essential to match the demand for fractions containing smaller molecules from the refinery process
- describe the difference between saturated and unsaturated hydrocarbons from their molecular structures and by using aqueous bromine
- describe the reactions of alkenes (exemplified by ethene) in terms of combustion, polymerisation (see also 11.4(b)), and the addition with bromine, steam and hydrogen
- state the meaning of polyunsaturated when applied to food products
- describe the manufacture of margarine by the addition of hydrogen to unsaturated vegetable oils to form a solid product.
Alkenes are not “just hydrocarbons”. They are tested through: (1) the C = C double bond (unsaturation), (2) bromine water test, (3) cracking as a source, and (4) addition reactions (hydrogenation/hydration/polymerisation).
1. Definition
A. Alkene
An alkene is an unsaturated hydrocarbon containing a carbon-carbon double bond, C = C. Alkenes with one double bond form a homologous series with general formula CₙH₂ₙ.
B. Unsaturated hydrocarbon
An unsaturated hydrocarbon is a hydrocarbon that contains at least one C = C bond.
C. Addition reaction
An addition reaction is a reaction where atoms add across a C = C double bond to form a single product.
2. Key Ideas
- General formula (for one C = C): CₙH₂ₙ.
- There is no “methene”: you need at least two carbon atoms to have C = C.
- Alkenes are more reactive than alkanes because the C = C bond can undergo addition reactions.
- Bromine water test: alkene decolourises red-brown bromine water to colourless (alkane does not, under normal conditions).
- Cracking breaks long-chain alkanes into shorter alkanes and alkenes (and hydrogen may also be produced).
- Complete combustion of ethene forms carbon dioxide and water.
- Addition polymerisation makes polymers like poly(ethene) from many alkene monomers.
- Polyunsaturated means a molecule contains more than one C = C bond.
Alkanes (contrast with substitution): Alkanes
Fuels + cracking context: Fuels and crude oil
Alcohols (product of hydration): Alcohols
3. Detailed Explanations
- Alkenes are unsaturated hydrocarbons with a C = C bond; general formula CₙH₂ₙ (for one double bond).
- Bromine water test: red-brown Br₂(aq) → colourless (alkene). Alkanes show no change in this test under normal conditions.
- Addition reactions happen across C = C: hydrogenation (H₂), hydration (steam → alcohol), polymerisation (many monomers → polymer).
- Cracking: long-chain alkanes → shorter alkanes + alkenes (high temperature + catalyst).
- Complete combustion of ethene produces CO₂ and H₂O.
- You need at least 2 carbons for C = C, so there is no “methene”.
A. General formula and examples
Alkenes (with one C = C) have general formula CₙH₂ₙ.
Unbranched alkenes you should be able to name:
| Name (unbranched) | Molecular formula | One-line structural formula |
|---|---|---|
| ethene | C₂H₄ | CH₂=CH₂ |
| propene | C₃H₆ | CH₂=CH–CH₃ |
Required C4 alkenes and isomers
| Name (unbranched) | Molecular formula | One-line structural formula |
|---|---|---|
| but-1-ene | C₄H₈ | CH₂=CH–CH₂–CH₃ |
| but-2-ene | C₄H₈ | CH₃–CH=CH–CH₃ |
Branched alkene example (same formula, different structure):
| Name (branched) | Molecular formula | One-line structural formula |
|---|---|---|
| 2-methylpropene (methylpropene) | C₄H₈ | CH₂=C(CH₃)₂ |
There is no “methene” because a C = C bond requires at least two carbon atoms.
B. Manufacture: cracking (thermal decomposition)
Cracking breaks long-chain alkanes into smaller molecules (short-chain alkanes and alkenes).
Essential conditions:
- high temperature,
- catalyst: aluminium oxide (Al₂O₃) or silicon dioxide (SiO₂).
Example equation: C₁₀H₂₂ → [heat][catalyst] C₈H₁₈ + C₂H₄
Cracking can also produce hydrogen, for example: C₂H₆ → C₂H₄ + H₂
Cracking is useful because refineries often have more large hydrocarbon molecules than customers need. It converts them into smaller fuel molecules and alkenes, which are in greater demand and can be used to make other chemicals.
C. Combustion
Ethene burns completely in a plentiful supply of oxygen to form carbon dioxide and water: C₂H₄(g) + 3O₂(g) → 2CO₂(g) + 2H₂O(l)
D. Addition reactions
Alkenes undergo addition reactions because the C = C bond opens up and new atoms attach.
1) Hydrogenation (add H₂)
Ethene + hydrogen → ethane: C₂H₄(g) + H₂(g) → C₂H₆(g)
Conditions: heat and a nickel catalyst.
Application: hydrogenation of vegetable oils (unsaturated) to make margarine (more saturated).
2) Bromination (test for unsaturation)
Alkenes react with bromine water (aqueous bromine, Br₂(aq)).
Observation: red-brown → colourless.
Example: C₂H₄(g) + Br₂(aq) → C₂H₄Br₂(aq)
Write: “red-brown bromine water decolourises to colourless”. Also write: “alkanes show no change under normal conditions”.
Bromine water is toxic/irritant. In practical questions, “wear gloves/eye protection” is acceptable.
3) Hydration (add steam)
Ethene + steam → ethanol: C₂H₄(g) + H₂O(g) → [high\ temperature,\ high\ pressure][H₃PO₄] C₂H₅OH(l)
Conditions: high temperature and pressure with a phosphoric(V) acid catalyst (H₃PO₄). Exact temperature and pressure values are not required.
4) Addition polymerisation
Many alkene monomers join to form a polymer.
Ethene → poly(ethene): n(CH₂ = CH₂) → [-CH₂-CH₂-]ₙ
Key terms:
- monomer: small molecule that repeats,
- polymer: long chain made from many monomers,
- repeating unit: the repeated section in the polymer.
E. Polyunsaturated food products and margarine
An unsaturated oil contains at least one C = C bond. Polyunsaturated means its molecules contain more than one C = C bond.
During margarine manufacture, hydrogen adds across some of these double bonds. This makes the vegetable oil more saturated and produces a solid product.
4. Common Mistakes
- Writing “bromine turns clear” (say “red-brown to colourless”).
- Writing that alkanes react with bromine water at room temperature (they do not, without UV).
- Mixing up cracking with fractional distillation (cracking is chemical change; distillation is physical separation).
- Forgetting conditions (temperature/catalyst) for cracking and hydration.
- Writing the hydration product as “ethane” (it is ethanol).
5. Exam Tips
Write: “long-chain alkanes”, “high temperature”, “catalyst (Al₂O₃ or SiO₂)”, “short-chain alkanes and alkenes”.
Write: “steam”, “high temperature and pressure”, and “phosphoric(V) acid catalyst (H₃PO₄)”.
6. Worked Examples
Modelled example 1
General formula check
Problem
Study the worked solution
Choose the alkene formula
Method
Use CₙH₂ₙ for an alkene with one double bond.Reason
The formula relates the hydrogen subscript to the number of carbon atoms.Working
For C₅H₁₀, n = 5.Substitute and compare
Method
Calculate the required number of hydrogen atoms.Reason
2n = 2(5) = 10, matching the given formula.Working
C₅H₁₀ fits CₙH₂ₙ, so it can be an alkene.
Guided practice 2
Bromine water test (distinguish alkane vs alkene)
Problem
Choose the reagent and observations
Hints
Hint 1: bond difference
Hint 2: observation wording
View solution step by step
Add the test reagent
Method
Add red-brown bromine water to separate samples.Reason
Bromine undergoes addition across an alkene’s C = C bond.Working
Use equal small samples so their observations can be compared.Distinguish the samples
Method
Identify ethene by decolourisation and ethane by no change.Reason
Ethene is unsaturated; ethane has no double bond and does not react under normal conditions.Working
Ethene: red-brown → colourless. Ethane: remains red-brown.
Common misconception 3
Polymerisation (repeating unit)
Learner structure
Track the alkene bond
View solution step by step
Open the double bond
Method
Replace the C = C in each ethene monomer with a C-C bond.Reason
The additional bonding capacity joins each monomer to its neighbours in the growing chain.Working
CH₂ = CH₂ monomer → single-bonded carbon atoms in the polymer.Write the repeating unit
Method
Show an outward bond at both ends of -CH₂-CH₂-.Reason
Those bonds indicate continuation of the polymer chain.Working
Repeating unit: -CH₂-CH₂-.
Examiner practice 4
Hydration conditions (ethene → ethanol)
Examination question
Give the complete industrial conditions
View solution step by step
State the reagent
1 markMethod
Use steam, H₂O(g).Reason
Hydration adds the components of water across C = C.Working
Reagent: steam.State temperature
1 markMethod
Use a high temperature.Reason
High temperature is the required level of detail; an exact value is not required.Working
Condition: high temperature.State pressure
1 markMethod
Use high pressure.Reason
The industrial hydration process operates at elevated pressure.Working
Condition: high pressure.State the catalyst
1 markMethod
Use phosphoric(V) acid, H₃PO₄.Reason
It catalyses the addition of steam to ethene.Working
Steam at high temperature and pressure with a H₃PO₄ catalyst.
Self-mark with the mark scheme
Compare your response with each mark point. Select a point only when your response contains that evidence.
Self-mark the reagent, essential conditions and catalyst.
Challenge 5
Cracking products (logic)
Equation transfer
Use atom conservation to find the missing product
Hints
Hint 1: subtract atoms
Hint 2: series check
View solution step by step
Conserve carbon
Method
Subtract the two carbon atoms in ethene from the ten in decane.Reason
Cracking rearranges atoms; it does not create or destroy them.Working
10-2 = 8 carbon atoms remain.Conserve hydrogen
Method
Subtract the four hydrogen atoms in ethene from the 22 in decane.Reason
The missing product must contain all remaining hydrogen atoms.Working
22-4 = 18, giving C₈H₁₈.Check and write the equation
Method
Confirm C₈H₁₈ is an alkane and write the products.Reason
For n = 8, 2n + 2 = 18 and both sides now have identical atom totals.Working
C₁₀H₂₂ → C₈H₁₈ + C₂H₄.
7. Mind Stretchers
Mind stretcher 1: Error analysis (bromine water)Extension
Question: A student writes: “Alkenes turn bromine water from colourless to red-brown.” Explain the error and correct it.
Show Answer
The direction is reversed.
Correct observation: bromine water is red-brown and turns colourless when it reacts with an alkene.
Final: red-brown → colourless (not colourless → red-brown).
Mind stretcher 2: Cracking vs distillation (trap)Extension
Question: A student says: “Cracking separates crude oil into fractions.” Replace this with a correct sentence for cracking and a correct sentence for fractional distillation.
Show Answer
Cracking: breaks long-chain hydrocarbons into smaller molecules (alkanes and alkenes) using heat and a catalyst (chemical change).
Fractional distillation: separates crude oil into fractions by different boiling points (physical separation).
Final: Cracking changes molecules; distillation separates a mixture.
8. Quiz
Test general formula, bromine-water observations, cracking conditions, and key addition reactions.