1.10Unit 1. Structure, Bonding and Introduction to Organic Chemistry
Alkanes — IAL Edexcel Linear (Chemistry) Revision Notes & Topical Questions
5 min read 12 parts Lesson 12 of 36 1 quiz
Curriculum Equation Key معادلة تفاعل تكوين الإستر (الأسترة) - Esterification Reaction EquationFast Exam Solution
R-COOH + R2-OH ⇌ (conc. H₂SO₄) R-COO-R2 + H₂O
Word Equation & Conditions: حمض كربوكسيلي + كحول (في وجود حمض الكبريتيك المركز كعامل حفاز ونازع للماء) ⇌ إستر + ماء
Location & Specifications: الكيمياء العضوية للثانوية العامة والتحصيلي و Edexcel Chemistry.
Lesson summary
1.10 Alkanes — structure, combustion, fuels, pollutants and free-radical substitution — IAL EDEXCEL LINEAR (CHEMISTRY) notes: Describe the structure and low reactivity of alkanes, their use and combustion as fuels, the resulting pollutants and alternative fuels, and the free-radi…
- Hydrocarbon
- High bond enthalpies
- Very low polarity
- Complete combustion
- Carbon monoxide
- Oxides of sulfur
Part 1 of 10Structure of alkanes
Structure of alkanes
Hydrocarbon
- Hydrocarbon a compound containing hydrogen and carbon only;
- alkanes and alkenes are aliphatic, arenes are aromatic.
Alkanes are saturated with general formula CnH2n+2.
- They contain only single bonds and no functional group.
- They are named alk + ane, with stems meth-, eth-, prop-, but-, pent- and then hex-, hept- and so on.
- Each carbon is tetrahedral, with bond angles of 109.5°.
Alkanes can be linear, branched or cyclic.
- Cycloalkanes are named cyclo + alk + ane and have formula CnH2n, the same as alkenes, but are still saturated.
Part 2 of 10Low reactivity of alkanes
High bond enthalpies
- C-C is 316 kJ mol−1 and C-H is 411 kJ mol−1.
- C-H is stronger because hydrogen has only one shell, so the nuclei are closer and attract the shared pair more strongly.
Very low polarity
- Very low polarity carbon and hydrogen have very similar electronegativities,
- so the σ bonds are almost non-polar and attract neither nucleophiles nor electrophiles.
Part 3 of 10Fractional distillation, cracking and reforming
Crude oil is a mixture of alkanes, cycloalkanes and arenes that is separated in an oil refinery by fractional distillation into fractions by boiling point.
Cracking
- Cracking heavier fractions are broken into smaller, more useful alkanes and alkenes of lower Mr,
- because small fractions such as gasoline are in higher demand.
- Example: decane gives octane and ethene.
- Thermal cracking uses up to 1000 °C and up to 70 atm and gives alkanes and a lot of alkenes.
- Catalytic cracking uses about 450 °C and slight pressure with a zeolite or aluminium oxide catalyst and gives mainly aromatic hydrocarbons.
Reforming
- Reforming straight-chain alkanes are converted to branched alkanes and cycloalkanes, usually with a platinum catalyst.
- Straight-chain alkanes tend to explode rather than burn smoothly in an engine, which is called knocking and lowers efficiency.
- Octane can be reformed to 2,5-dimethylhexane.
- Hexane can be reformed to cyclohexane, C6H12, and H2.
Part 4 of 10Combustion of alkanes
Complete combustion
- Complete combustion excess oxygen oxidises all carbon to CO2 and all hydrogen to H2O.
- CH4 + 2O2 → CO2 + 2H2O.
Incomplete combustion
- Incomplete combustion limited oxygen forms carbon monoxide, and with less oxygen still, carbon as soot.
- 2CH4 + 3O2 → 2CO + 4H2O.
- It often happens in a car engine where oxygen is limited.
- Solid carbon particles (particulates) clump together as soot.
Part 5 of 10Pollutants from burning fuels
Carbon monoxide
- Carbon monoxide a toxic, odourless gas that causes dizziness, loss of consciousness and death.
- It binds strongly to haemoglobin, which then cannot carry oxygen and carbon dioxide.
Oxides of sulfur
- Oxides of sulfur sulfur impurities form SO2 and SO3, which dissolve to form H2SO3 and H2SO4 and cause acid rain.
- S + O2 → SO2 and 2SO2 + O2 → 2SO3.
- Acid rain kills aquatic life, damages crops and forests, corrodes metals and releases CO2 from carbonate rocks and buildings.
Oxides of nitrogen
- Oxides of nitrogen the high temperature and pressure in an engine oxidise nitrogen, N2 + O2 → 2NO and N2 + 2O2 → 2NO2.
- NO2 dissolves to form HNO2 and HNO3, which cause acid rain.
- NOx reacts with unburnt hydrocarbons (VOCs) to form peroxyacetyl nitrate (PAN), the main pollutant of photochemical smog,
- which harms lungs, eyes and plants.
Particulates (soot) and unburnt hydrocarbons are also released in exhaust fumes.
Part 6 of 10Catalytic converters
Catalytic converters
A honeycomb coated with platinum, rhodium and palladium gives a large surface area for reaction.
Reactions in the converter
- Oxidation of unburnt hydrocarbonsCnH2n+2 + (3n+1)[O] → nCO2 + (n+1)H2O.
- Oxidation of CO2CO + O2 → 2CO2.
- Reduction of NO by CO2CO + 2NO → 2CO2 + N2.
Nitrogen oxides are reduced on the hot catalyst surface to unreactive, harmless nitrogen gas.
Part 7 of 10Alternative fuels and carbon neutrality
Alternative fuels reduce pollution and global warming from fossil fuels and replace depleting non-renewable reserves.
Biofuels are renewable fuels from living matter.
- Biodiesel is made by refining renewable fats and oils.
- Bioethanol is made by fermentation of sugars with yeast.
- Biogas is released when organic waste breaks down.
Benefits of biofuels
- They are often considered carbon neutral.
- Biodiesel and biogas reduce waste going to landfill.
- Crop growing can bring income to less developed countries.
Drawbacks of biofuels
- Engines and machinery are expensive to convert.
- Land needed for food production limits how much can be grown.
- Growing, harvesting, processing and transport use energy, so they are not fully carbon neutral.
Carbon neutral
- Carbon neutral no net change in the amount of CO2 in the atmosphere.
- A growing plant absorbs CO2 that is released when it is burnt.
- Fossil fuels are not carbon neutral because the CO2 they absorbed millions of years ago was at a higher atmospheric level.
Hydrogen
- 2H2 + O2 → 2H2O is carbon neutral.
- Its low density makes storage difficult and it is explosive.
- Producing hydrogen is expensive, which limits its use.
Greenhouse effect
- CO2, methane and water vapour absorb the infrared radiation re-emitted by the Earth and trap heat.
- Rising CO2 causes the enhanced greenhouse effect.
Part 8 of 10Free radicals and bond fission
Heterolytic fission
- Heterolytic fission the more electronegative atom takes both bonding electrons, forming a negative ion and a positive ion.
- A double-headed arrow shows the movement of an electron pair.
- The negative ion is a nucleophile; the positive ion is an electrophile.
Homolytic fission
- Homolytic fission each atom takes one bonding electron, forming two free radicals.
- A free radical is a species with an unpaired electron.
- Single-headed (fish-hook) arrows show the movement of one electron.
- Cl-Cl splits into two chlorine radicals, Cl•.
Part 9 of 10Free-radical substitution mechanism
Alkanes are unreactive, so UV light (sunlight) is needed for a halogen to substitute a hydrogen atom.
Initiation
- UV energy breaks Cl-Cl or Br-Br homolytically.
- Cl2 → 2Cl•.
Propagation
- Propagation a chain reaction in which radicals are used and regenerated.
- Cl• + CH4 → HCl + •CH3.
- •CH3 + Cl2 → CH3Cl + Cl•.
Termination
- Termination two radicals combine to form a single unreactive molecule.
- Cl• + •CH3 → CH3Cl.
- •CH3 + •CH3 → C2H6.
Bromine colour disappears only when mixed with an alkane in sunlight, which shows UV is essential.
Part 10 of 10Limitations of free-radical substitution
1
Further substitution gives a mixture of products.
- Excess chlorine forms CH2Cl2, CHCl3 and CCl4, and with enough halogen all hydrogens are replaced (ethane gives C2Cl6).
- Excess methane favours monosubstitution.
2
Termination can give impurities such as ethane from •CH3 + •CH3.
3
Longer alkanes can substitute at different carbon atoms.
- For propane and bromine, a middle-carbon radical CH3•CHCH3 gives 2-bromopropane.
4
The reaction is therefore a poor way to prepare one pure halogenoalkane.
Key terms
| Term | Meaning |
|---|---|
| Hydrocarbon | A compound containing hydrogen and carbon only. |
| Saturated | Containing only single carbon-carbon bonds. |
| Cracking | Breaking long-chain alkanes into shorter alkanes and alkenes. |
| Reforming | Converting straight-chain alkanes into branched alkanes and cycloalkanes. |
| Complete combustion | Burning in excess oxygen to give only CO2 and H2O. |
| Free radical | A species with an unpaired electron. |
| Homolytic fission | Breaking a bond so that each atom takes one electron. |
| Carbon neutral | Having no net change in atmospheric CO2. |
| Propagation | A chain step in which a radical reacts and a new radical is formed. |
Avoid these mistakes
1
Giving the wrong reason for alkane unreactivity — bonds are strong and almost non-polar.
2
Writing curly double-headed arrows for radical steps — radicals use single-headed arrows.
3
Forgetting UV light as a condition of free-radical substitution — without it the reaction does not start.
4
Calling biofuels completely carbon neutral — energy is used in growing, processing and transport.
5
Saying incomplete combustion produces only CO — carbon (soot) can also form.
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