Full chapter
Organic Chemistry
Recognise molecular families and connect structures, reactions, fuels and materials.
SEC G2 Science K223 / K225 (2027)
Fuels, fractions and bioethanol
Follow carbon from a resource to useful products.
A hydrocarbon contains carbon and hydrogen only. Natural gas is mainly methane; crude oil is a mixture of hydrocarbons. Both are non-renewable because they form far more slowly than they are consumed. Burning a fuel releases energy, while the same hydrocarbon feedstock may also be valuable for manufacturing chemicals and plastics.
- Heat the oil
Many components vaporise.
- Vapour rises through the column
The column is hotter at the bottom and cooler at the top.
- Condense different fractions
Higher-boiling, generally larger molecules condense lower down; smaller, more volatile molecules travel higher.
- Collect useful mixtures
Each fraction contains hydrocarbons with a range of boiling points, not necessarily one pure compound.
As hydrocarbon molecules get larger, melting and boiling points generally rise overall, viscosity increases, and volatility decreases. Smaller fractions are useful fuels; larger fractions may be cracked into more sought-after smaller molecules. The amount supplied by fractional distillation need not match the demand for each fraction. Larger molecules generally have stronger intermolecular attractions, so more energy is needed to separate them and the liquid resists flow more. These are trends within comparable members, not a claim that every individual melting point rises smoothly.
Bioethanol can be made from sugars in a crop such as sugarcane and is renewable if the crop is regrown. Growing plants take in carbon dioxide, partly offsetting carbon dioxide released when the ethanol burns. Fossil fuels instead add carbon stored underground to the active carbon cycle. Biofuel is not automatically emission-free: cultivation, processing, transport and land-use change also affect its impact.
Check your understandingWhy is a crude-oil fraction not necessarily a pure substance?Think it through, then reveal the answer
Alkanes: build a valid carbon skeleton
Use four bonds per carbon and one per hydrogen.
A homologous series has a common general formula, similar chemical properties and a gradual change in physical properties as molecule size and mass increase. Successive members differ by CH2. Alkanes are saturated hydrocarbons: all carbon-carbon bonds are single. For an unbranched or branched acyclic alkane, the general formula is CnH2n+2.
| Name | Molecular formula | Condensed structure |
|---|---|---|
| Methane | CH4 | One C with four C-H bonds |
| Ethane | C2H6 | CH3-CH3 |
| Propane | C3H8 | CH3-CH2-CH3 |
To draw a displayed formula, draw the carbon-carbon connections first, then add individual C-H bonds until each carbon has four bonds. A condensed CH3 group stands for three separate hydrogens bonded to that carbon. Count atoms after drawing; moving the page or bending a chain does not create a new compound.
Four bonds around carbon
Methane has four single C-H bonds. Each ethene carbon has two C-H bonds and a double C=C bond, giving four bonds in total.
Displayed methane
Complete displayed structure with 1 carbon, 4 hydrogen atoms: CH4. Every bond and hydrogen is shown.
Displayed ethane
Complete displayed structure with 2 carbon, 6 hydrogen atoms: C2H6. Every bond and hydrogen is shown.
Displayed propane
Complete displayed structure with 3 carbon, 8 hydrogen atoms: C3H8. Every bond and hydrogen is shown.
Alkanes are generally unreactive, but burn and undergo substitution with chlorine in ultraviolet light. Complete combustion: CH4(g) + 2O2(g) -> CO2(g) + 2H2O(l), showing cooled products. Limited oxygen can produce carbon monoxide and/or soot. Substitution: CH4(g) + Cl2(g) -> CH3Cl(g) + HCl(g), under UV. One H is replaced by Cl; further substitution is possible.
Check your understandingA saturated acyclic hydrocarbon contains three carbon atoms. What formula should it have, and how do you check a drawing?Think it through, then reveal the answer
Alkenes: a double bond creates new reactions
Distinguish substitution, addition and cracking.
Alkenes are unsaturated hydrocarbons containing a carbon-carbon double bond. For acyclic molecules with one C=C bond, their general formula is CnH2n. Ethene is CH2=CH2; propene is CH2=CH-CH3. Each carbon still has four bonds in total.
Worked example
Expand an alkene without adding too many hydrogens
Draw propene from CH2=CH-CH3.
- Join three carbon atoms. Put the double bond between the first two; this uses two of each participating carbon's four bonds.
- Carbon 1 needs two C-H bonds. Carbon 2 already has three bonds in total to carbons, so needs only one H. Carbon 3 needs three H.
- Count the result: C3H6, with four bonds at each carbon.
Use the displayed propene below as a check. A double bond counts twice for valency but still connects the same two carbon atoms.
Displayed ethene
Complete displayed structure with 2 carbon, 4 hydrogen atoms: C2H4. Every bond and hydrogen is shown.
Displayed propene
Complete displayed structure with 3 carbon, 6 hydrogen atoms: C3H6. Every bond and hydrogen is shown.
Aqueous bromine distinguishes an alkene from an alkane under the usual test conditions without UV. The alkene decolourises orange/brown bromine water because bromine adds across C=C. Ethene forms CH2Br-CH2Br. The alkane does not show this addition reaction. The colour change is an observation; unsaturation is the inference.
| Reagent or process | Essential conditions | Product/change |
|---|---|---|
| Oxygen: complete combustion | Ignition, sufficient oxygen | C2H4 + 3O2 -> 2CO2 + 2H2O |
| Aqueous bromine | Room conditions; no UV required | C2H4 + Br2 -> C2H4Br2 |
| Hydrogen | Nickel catalyst, heat | C2H4 + H2 -> C2H6 |
| Addition polymerisation | Suitable temperature, pressure and catalyst | Many ethene molecules form poly(ethene) |
Cracking breaks larger hydrocarbons into smaller molecules using strong heating, often with a catalyst. Products can include smaller alkanes, alkenes and hydrogen. Examples of possible balanced changes are C10H22 -> C8H18 + C2H4, and C2H6 -> C2H4 + H2. Actual cracking produces a mixture; use atom conservation to deduce a missing product.
Polyunsaturated food molecules contain more than one C=C bond. Hydrogenating unsaturated vegetable oils with hydrogen and a nickel catalyst reduces the number of double bonds, making the product more solid and useful in margarine manufacture. This is addition, not polymerisation.
Check your understandingC8H18 cracks to C6H14 and one other molecule. Deduce its formula.Think it through, then reveal the answer
Addition polymers: open the double bond, keep the substituents
A repeat unit shows the pattern within a long chain.
A polymer is a large molecule built from many smaller monomer molecules. Different monomers give different repeating units and properties. In addition polymerisation, the C=C bonds open to link monomers into a chain; no small molecule is eliminated. Poly(ethene) forms from ethene and is used in plastic bags and clingfilm.
- Start with the alkene
Identify the two carbon atoms of C=C.
- Change the double bond to a single bond
Give each of those carbons a new bond to the next unit.
- Preserve every attached group
Do not detach or lose hydrogens, chlorine atoms or side chains.
- Show repetition
Enclose a repeat unit in brackets, with backbone bonds extending through the brackets and n outside.
Ethene gives the repeat unit [-CH2-CH2-]n. Propene, CH2=CH-CH3, gives [-CH2-CH(CH3)-]n. The CH3 side group stays attached; it does not become a third carbon in the two-carbon backbone repeat.
Poly(ethene): bonds through the brackets
Two backbone carbon atoms have a single bond between them and open bonds passing through the brackets to neighbouring units. Each carbon has two hydrogen atoms.
Poly(propene): keep the side group
Two backbone carbon atoms have a single bond between them and open bonds passing through the brackets to neighbouring units. A complete CH3 side group remains attached to the second carbon.
Worked example
Recover a monomer
A polymer repeat unit is [-CH2-CHCl-]n. Deduce its monomer.
- Identify the two backbone carbons.
- Remove their links to neighbouring repeat units and restore a C=C double bond.
- Keep the chlorine attached to the same carbon.
CH2=CHCl. An unfamiliar monomer can be deduced from bonding without memorising its name.
Check your understandingShould a poly(ethene) repeat unit retain the original C=C double bond?Think it through, then reveal the answer
Evaluate plastic use and recycling
Compare what happens to the molecules and to the wider system.
Many plastics are non-biodegradable: natural biological processes do not break them down readily. Persistent waste can harm wildlife through ingestion or entanglement, accumulate in habitats and fragment into small pieces. Burning plastics releases carbon dioxide and, depending on the plastic and conditions, other pollutants. Disposal shifts a problem unless its consequences are considered.
| Route | What happens | Trade-off |
|---|---|---|
| Physical recycling | Sort and clean plastic, cut it into pieces, then melt it into pellets; poly(ethene) is an example | Retains polymer molecules but mixed materials or contamination can reduce product quality |
| Chemical recycling by cracking | Break plastic molecules into smaller hydrocarbons that can be used as fuel | Can process molecules differently, but requires energy; burning the fuel still releases carbon dioxide |
| Dimension | Questions that matter |
|---|---|
| Social | Is collection accessible? Are sorting instructions understandable? Are workers and nearby communities affected? |
| Economic | What do collection, transport, sorting and processing cost? Is there a market for the recovered material? |
| Environmental | How much energy, transport and virgin resource use are avoided or added? What emissions and unrecovered waste remain? |
Worked example
Compare two claims
One plan melts clean separated poly(ethene) locally; another ships mixed plastic far away for cracking. Is either always better?
- The first may use less processing but depends on clean sorted input and a useful output market.
- The second may accept different waste but adds transport and cracking energy.
- Compare actual quantities, energy sources, yields and avoided virgin production.
A justified decision uses evidence across the whole process, rather than assuming the word recycling guarantees a lower impact.
Check your understandingDoes melting poly(ethene) into pellets normally turn it back into ethene?Think it through, then reveal the answer
Quick revision
Revisit the essentials, then return to an explanation when you need it.
- Alkane
Combustion; chlorine substitution under UV; larger molecules can crack.
- Alkene
Bromine/hydrogen addition and addition polymerisation.
- Polymer
Match the repeat unit to its monomer; distinguish physical and chemical recycling.
Scope
Learning outcomes
8. Organic Chemistry (K223 / K225). Use the outcome map to find the explanation for a particular syllabus requirement.
See the learning outcome map
8.1(a) Identify non-renewable fuel sources
- Natural gas mainly methane
- Crude oil
8.1(b) Explain crude-oil fractionation
- Hydrocarbon mixture
- Fractions
- Competing fuel and chemical feedstock uses
8.1(c) Recognise renewable biofuel
- Bioethanol from sugarcane
8.1(d) Compare carbon impacts of fuels
- Plant-growth uptake offsets burning emissions
- Compare fossil-carbon release
- Sustainability depends on wider inputs
8.2(a) Describe homologous series
- General formula
- Similar chemistry
- Gradual melting/boiling/viscosity change with size/mass
Alkanes: build a valid carbon skeletonFuels, fractions and bioethanol
8.2(b) Describe alkanes
- Saturated hydrocarbons
- CnH2n+2
8.2(d) Describe alkane reactions
- Methane combustion
- Chlorine substitution with UV
- Generally unreactive otherwise
8.2(e) Describe alkenes
- Unsaturated hydrocarbons
- CnH2n
8.2(g) Explain cracking
- Alkenes and hydrogen products
- Demand for smaller refinery molecules
- Heating/catalyst conditions
Alkenes: a double bond creates new reactionsFuels, fractions and bioethanol
8.2(h) Distinguish saturation
- Molecular structure
- Aqueous bromine test
8.2(j) Explain polyunsaturated food molecules
- More than one C=C
8.2(k) Explain margarine manufacture
- Hydrogen addition to vegetable oils
- Solid product
- Nickel catalyst and heat
8.2(c) Draw and name alkanes
- Unbranched C1-C3
- Methane to propane
8.2(f) Draw and name alkenes
- Unbranched C2-C3
- Ethene and propene
8.2(i) Describe ethene reactions
- Combustion
- Polymerisation
- Bromine and hydrogen addition
- Essential conditions
Alkenes: a double bond creates new reactionsAddition polymers: open the double bond, keep the substituents
8.3(a) Describe polymers and monomers
- Large molecules from small units
- Different monomers give different polymers
Addition polymers: open the double bond, keep the substituents
8.3(b) Explain poly(ethene) formation
- Addition polymerisation of ethene
Addition polymers: open the double bond, keep the substituents
8.3(c) Identify poly(ethene) uses
- Plastic bags
- Clingfilm
Addition polymers: open the double bond, keep the substituents
8.3(d) Deduce addition-polymer structures
- Monomer to repeat unit
- Repeat unit to monomer
Addition polymers: open the double bond, keep the substituents
8.3(e) Explain plastic pollution
- Non-biodegradability
- Disposal impacts
8.3(f) Compare recycling routes
- Physical: poly(ethene) melted into pellets
- Chemical: cracking into fuel
8.3(g) Evaluate recycling issues
- Social
- Economic
- Environmental