Topic 4: Introductory Organic Chemistry AS and Alkanes
- Syllabus
- 2017
- Topic
- —
- Level
- AS
| Term | Meaning | What can change? |
|---|---|---|
| hazard | the inherent potential of a substance or procedure to cause harm | the hazard classification normally remains fixed for that substance and use |
| risk | the likelihood and possible severity of harm under particular conditions | amount, concentration, exposure route, duration and controls can all change it |
Concentrated hydrochloric acid is corrosive: that is its hazard. Using a large open beaker near eye level creates a higher risk than handling a few drops in a tray while wearing eye protection, because exposure is more likely or consequential.
Risk assessment therefore asks: what harm can occur, who or what could be exposed, how likely and severe is it, and which controls reduce that risk to an acceptable level?
A control measure reduces risk; it does not usually remove the chemical's inherent hazard. Do not use 'hazard' and 'risk' as synonyms.
| Common organic-chemistry hazard | Possible source | Potential harm |
|---|---|---|
| flammable | volatile solvents and fuels | ignition, fire and burns |
| harmful or toxic | vapours, products or reagents | harm by inhalation, ingestion or skin exposure |
| corrosive | strong acids or alkalis used with organic substances | tissue and eye damage |
| irritant | some vapours and liquids | skin, eye or respiratory irritation |
| environmental hazard | persistent or toxic releases | harm to organisms and ecosystems |
A risk assessment identifies the substances, quantities, concentrations, temperatures, apparatus, exposure routes and people involved. It then selects controls, records emergency action and considers disposal before work begins.
Organic compounds are often volatile and flammable, so vapour can spread beyond the vessel and meet an ignition source. The same chemical can present very different risks at microscale and at bulk scale.
A hazard pictogram identifies a class of harm; it does not by itself state the risk of the planned procedure. Conditions and controls must also be assessed.
| Risk-reduction route | Example | Why risk falls |
|---|---|---|
| work on a smaller scale | use millilitres rather than tens of millilitres | less material and energy are available if something goes wrong |
| take hazard-specific precautions | use a fume cupboard for toxic vapour; exclude flames for a flammable solvent; wear eye protection for splashes | the control blocks the relevant exposure or ignition route |
| use a less hazardous method | replace a toxic or highly flammable reagent where a suitable safer alternative exists | the initiating hazard is reduced or removed |
Prefer controls that remove or contain the hazard before relying only on personal protective equipment. Check ventilation, heating method, secure apparatus, spill response and waste route for the actual procedure.
For carbon monoxide, improve containment and ventilation, use a fume cupboard or suitable extraction, monitor where necessary, and limit exposure time. Gloves alone do not control an inhalation hazard.
A generic precaution is not enough: the control must match the hazard and exposure route. A smaller scale reduces consequences but does not make unsafe technique acceptable.
A homologous series is a family of organic compounds with the same functional group and general formula, similar chemical reactions, and a gradual trend in physical properties. Successive members differ by CH2.
A functional group is the atom or group of atoms responsible for the characteristic reactions of an organic compound. Examples include C=C in alkenes, –OH in alcohols and –COOH in carboxylic acids.
| Series | Functional feature | General formula for the relevant acyclic series |
|---|---|---|
| alkanes | C–C and C–H single bonds only | CnH2n+2 |
| alkenes | C=C | CnH2n |
| alcohols | –OH | CnH2n+1OH |
Members of a homologous series do not have identical physical properties: boiling temperature usually changes gradually with chain length. Similar chemistry comes from the shared functional group.
| Carbon atoms | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 |
|---|---|---|---|---|---|---|---|---|---|---|
| stem | meth- | eth- | prop- | but- | pent- | hex- | hept- | oct- | non- | dec- |
Choose the longest parent chain containing the principal functional group and any required multiple bond. Number from the end giving the lowest relevant locants. Name and alphabetise substituents, use di-, tri- or tetra- for repeats, then add the suffix and locant for the functional group.
CH3C(CH3)2CH2CH(CH3)CH3 has a five-carbon parent chain and methyl groups at 2, 2 and 4, so its name is 2,2,4-trimethylpentane. Commas separate numbers and hyphens separate numbers from words.
| Representation | What must be shown |
|---|---|
| structural/condensed | connectivity in grouped form, such as CH3CH2OH |
| displayed | every atom and every bond |
| skeletal | carbon-chain lines and vertices; C and attached H atoms are omitted, but heteroatoms and their H atoms are shown |
The visually straightest line is not necessarily the longest carbon chain. Trace all connected carbon routes before selecting and numbering the parent.
| Reaction class | Recognising change | Example pattern |
|---|---|---|
| addition | two reactants form one main product across a multiple bond | C=C becomes C–C as atoms add |
| substitution | one atom or group is replaced by another | alkane H replaced by Cl |
| oxidation | oxygen is gained or hydrogen is lost | primary alcohol to aldehyde |
| reduction | hydrogen is gained or oxygen is lost | C=O to C–OH |
| polymerisation | many monomers join to form a long-chain molecule | many alkenes form an addition polymer |
Compare bonds and functional groups in reactants and products. Classify the actual transformation, not the reagent name: converting C=C to C–C by adding atoms is addition, while replacing C–H by C–Cl is substitution.
A reaction can involve more than one change in a complex molecule. Name the class for the specified position or step rather than forcing the whole scheme into one label.
| Bond breaking | Electron movement | Products | Arrow convention |
|---|---|---|---|
| homolytic fission | one bonding electron goes to each atom | two free radicals | two curly half-arrows, each moving one electron |
| heterolytic fission | both bonding electrons go to one atom | a cation and an anion | a full curly arrow, moving an electron pair |
Under ultraviolet light, Cl–Cl can split homolytically: Cl2→2Cl⋅. H–Cl can be represented as breaking heterolytically to H+ and Cl− when both electrons go to chlorine.
After drawing arrows, count electrons and charges in every product. A radical has an unpaired electron; heterolysis produces opposite charges whose total equals the reactant charge.
Homolytic does not mean the bond breaks into ions. Equal electron division makes radicals; unequal division makes ions.
| Species | Definition | Typical notation/example |
|---|---|---|
| free radical | a species with an unpaired electron | Cl⋅ or CH3$\boldsymbol{\cdot}$ |
| electrophile | an electron-pair acceptor | H+ accepts a lone pair; Brδ+ can accept a pair during addition |
The unpaired electron makes many radicals highly reactive. An electrophile is electron-deficient and is attracted to an electron-rich region such as a lone pair or a π bond.
A radical is defined by an unpaired electron, not by having a charge. An electrophile accepts an electron pair; it need not carry a full positive charge.
| Family | General formula | Structural feature |
|---|---|---|
| acyclic alkane | CnH2n+2 | open chain; C–C single bonds only |
| monocyclic cycloalkane | CnH2n | one carbon ring; C–C single bonds only |
A hydrocarbon contains carbon and hydrogen only. Saturated means that it contains no carbon–carbon multiple bond, so each carbon has the maximum number of hydrogen atoms allowed by its C–C connectivity.
Closing an alkane chain to make one ring removes two hydrogen atoms, which explains the change from CnH2n+2 to CnH2n. For example, propane is C3H8 and cyclopropane is C3H6.
CnH2n does not prove that a compound is a cycloalkane; an acyclic alkene can have the same general formula. Inspect the bonds and ring connectivity.
Structural isomers are compounds with the same molecular formula but different structural formulae: their atoms are connected in different ways.
C4H10 can be CH3CH2CH2CH3 (butane) or CH3CH(CH3)CH3 (2-methylpropane). Both contain four carbons and ten hydrogens, but the carbon skeletons differ.
To find isomers, vary the carbon skeleton, functional-group position or functional group where the formula permits it. After each drawing, recount atoms, check valencies, assign an IUPAC name and reject any structure that is just a rotated or renumbered duplicate.
Different orientations of the same connectivity are not structural isomers. A molecular formula alone also does not show which atoms are connected.
| Formula | Distinct alkane names |
|---|---|
| C4H10 | butane; 2-methylpropane |
| C5H12 | pentane; 2-methylbutane; 2,2-dimethylpropane |
| C6H14 | hexane; 2-methylpentane; 3-methylpentane; 2,2-dimethylbutane; 2,3-dimethylbutane |
For a cycloalkane, choose a ring size from three up to the total carbon count, then distribute the remaining carbons as substituents. Number substituted rings to give the lowest set of locants and reject rotations, reflections and alternative numbering of the same connectivity.
C4H8 gives cyclobutane and methylcyclopropane. For C5H10, valid connectivities include cyclopentane, methylcyclobutane, ethylcyclopropane, 1,1-dimethylcyclopropane and 1,2-dimethylcyclopropane. This same ring-size method extends to six carbons.
Use displayed, structural or skeletal formulae consistently. In a skeletal ring, every unlabelled vertex is carbon and enough hydrogens are implied to give carbon four bonds.
Cis/trans forms have the same connectivity and are stereoisomers, not additional structural isomers. Do not double-count them in a structural-isomer list.
| Process | What happens | Chemical or physical? | Example/evidence |
|---|---|---|---|
| fractional distillation | hydrocarbons separate by boiling range in a temperature gradient | physical separation | lower-boiling fractions condense higher in the column |
| cracking | long-chain molecules split into smaller, more useful molecules | chemical reaction | C10H22→C8H18+C2H4 |
| reforming | straight chains rearrange to branched, cyclic or aromatic products with improved fuel quality | chemical reaction | C6H14→C6H12+H2 for cyclisation with dehydrogenation |
Alkanes burn exothermically, so fractions containing them are used as fuels. Supply and demand rarely match crude-oil composition, so cracking increases smaller fuels and alkene feedstocks, while reforming improves combustion quality.
For every cracking or reforming equation, conserve the number of carbon and hydrogen atoms. Fractional distillation has no reaction equation because no covalent bonds change.
Cracking does not simply separate an existing mixture: it breaks covalent bonds and makes new molecules. Fractional distillation separates without changing molecular identities.
| Pollutant | How it arises during fuel use |
|---|---|
| carbon monoxide, CO | incomplete combustion when oxygen is insufficient |
| carbon particulates (soot) | very incomplete combustion of hydrocarbon fuel |
| unburned hydrocarbons | fuel escapes combustion or burns incompletely |
| nitrogen oxides, NOx | N2 and O2 from air react at high engine temperatures |
| sulfur oxides, SOx | sulfur-containing impurities in fuel are oxidised |
Pollutant formation depends on fuel composition and combustion conditions. Improving oxygen mixing can reduce CO and soot, but high combustion temperature can favour nitrogen-oxide formation.
Carbon monoxide is not produced because carbon is absent; it forms when carbon-containing fuel is only partially oxidised. Nitrogen oxides come mainly from air at high temperature, not from the alkane formula.
| Pollutant | Specified problem | Causal explanation |
|---|---|---|
| carbon monoxide | toxicity | CO binds strongly to haemoglobin, reducing the blood's ability to transport oxygen |
| nitrogen oxides | acidity | they react with oxygen and water to form acidic solutions, contributing to acid deposition |
| sulfur oxides | acidity | they dissolve and oxidise in atmospheric water to form acids, contributing to acid deposition |
Acid deposition lowers the pH of soils and surface waters and can damage carbonate stone and living systems. In an enclosed space, incomplete combustion makes CO especially dangerous because it is colourless and toxic.
For this objective, keep the causal claim precise: CO toxicity is explained through haemoglobin and reduced oxygen transport; the specified issue for nitrogen and sulfur oxides is their acidity.
Alternative fuels are developed to reduce dependence on finite crude oil, improve long-term security of supply and reduce harmful or greenhouse-gas emissions over the fuel's life cycle.
| Criterion | Question for comparison |
|---|---|
| resource sustainability | Is the feedstock renewable, and how quickly is it replaced? |
| climate effect | How much net CO2-equivalent is emitted from production, transport and use? |
| air quality | Are CO, particulates, sulfur oxides or nitrogen oxides reduced? |
| practicality | What energy density, storage, infrastructure, land and cost are required? |
Combustion of fossil alkanes transfers geologically stored carbon to atmospheric CO2. CO2 absorbs outgoing infrared radiation, so increasing its concentration strengthens the greenhouse effect and contributes to climate change.
An alternative fuel is not automatically sustainable or low-carbon. Compare the complete production-and-use pathway, not tailpipe emissions alone.
A fuel is carbon neutral only if the amount of CO2 added to the atmosphere across its life cycle is balanced by CO2 removed or otherwise prevented from being added. The boundary must include production, processing and transport as well as use.
| Fuel | Carbon-neutrality judgment |
|---|---|
| petrol | not carbon neutral: combustion releases fossil carbon, with further emissions from extraction and refining |
| bioethanol | potentially close to neutral for biogenic carbon because growing plants absorb CO2, but farming, fertiliser, processing, transport and land-use change create additional emissions |
| hydrogen | produces water and no CO2 at point of use, but neutrality depends on how H2 is made; renewable electrolysis can be low-carbon, fossil-fuel production is not |
State the system boundary, identify every carbon or energy input, compare atmospheric uptake with emissions, and give a conditional conclusion rather than relying on a label such as 'bio' or 'hydrogen'.
Zero carbon at the exhaust is not the same as carbon neutral. Upstream energy and feedstock can dominate the life-cycle balance.
| Reaction | Conditions and products | Example |
|---|---|---|
| complete combustion | excess oxygen; CO2 and H2O | CH4+2O2→CO2+2H2O |
| incomplete combustion | limited oxygen; CO and/or C plus H2O | 2CH4+3O2→2CO+4H2O |
| halogen substitution | chlorine or bromine with ultraviolet light; an H atom is replaced by halogen | CH4+Cl2→CH3Cl+HCl |
To balance complete combustion of CxHy, form xCO2 and y/2H2O, then balance O2. Include state symbols when requested.
The carbon skeleton remains while a C–H bond and X–X bond are replaced by C–X and H–X bonds. Ultraviolet radiation initiates radical formation.
Halogen reaction with an alkane is substitution, not addition, because the saturated carbon skeleton has no C=C bond for addition across.
| Stage | Methane/chlorine equation | Role |
|---|---|---|
| initiation | Cl2UV2Cl⋅ | homolytic fission creates radicals; draw two curly half-arrows from Cl–Cl |
| propagation 1 | Cl⋅+CH4→HCl+CH3⋅ | a radical is consumed and another radical formed |
| propagation 2 | CH3⋅+Cl2→CH3Cl+Cl⋅ | regenerates Cl⋅, continuing the chain |
| termination | Cl⋅+Cl⋅→Cl2; CH3⋅+Cl⋅→CH3Cl; 2CH3⋅→C2H6 | two radicals combine and no radical remains |
A curly half-arrow moves one electron. In each propagation step, use half-arrows so bond breaking and bond formation account for the unpaired electron without inventing charge.
The product can undergo further substitution because it still contains C–H bonds. Longer alkanes can also substitute at different carbon positions. The resulting mixture of products and isomers makes the reaction poorly selective for synthesis.
A propagation step must regenerate a radical; a termination step removes radicals. Do not label Cl2 homolysis as propagation—it is the initiation step.