know that a hydrocarbon is a compound of hydrogen and carbon only

be able to represent organic molecules using empirical formulae, molecular formulae, general formulae, structural formulae, displayed formulae and skeletal formulae

know what is meant by the terms ‘homologous series’ and ‘functional group’

be able to name compounds relevant to this specification using the rules of International Union of Pure and Applied Chemistry (IUPAC) nomenclature

Students will be expected to know prefixes for compounds up to C₁₀

be able to classify reactions as addition, elimination, substitution, oxidation, reduction, hydrolysis or polymerisation

understand the term ‘structural isomerism’ and determine the possible structural, displayed and skeletal formulae of an organic molecule, given its molecular formula

understand the term ‘stereoisomerism’, as illustrated by E/Z isomerism (including cis-trans isomerism where two of the substituent groups are the same)

know the general formula for alkanes

know that alkanes and cycloalkanes are saturated hydrocarbons

understand that alkane fuels are obtained from the fractional distillation, cracking and reforming of crude oil

Reforming is described as the processing of straight-chain hydrocarbons into branched-chain alkanes and cyclic hydrocarbons for efficient combustion.

know that pollutants, including carbon monoxide, oxides of nitrogen and sulfur, carbon particulates and unburned hydrocarbons, are formed during the combustion of alkane fuels

understand the problems arising from pollutants from the combustion of fuels, limited to the toxicity of carbon monoxide and the acidity of oxides of nitrogen and sulfur

understand how the use of a catalytic converter solves some problems caused by pollutants

understand the use of alternative fuels, including biodiesel and alcohols derived from renewable sources such as plants, in terms of a comparison withnon-renewable fossil fuels

know that a radical:

i) is a species with an unpaired electron and is represented in mechanisms by a single dot
ii) is formed by homolytic fission of a covalent bond and results in the formation of radicals

understand the reactions of alkanes with:

i) oxygen in air (combustion)
ii) halogens, in terms of the mechanism of radical substitution through initiation, propagation and termination steps

The use of curly half-arrows is not expected in this mechanism.

understand the limitations of the use of radical substitution reactions in the synthesis of organic molecules, in terms of further substitution reactions and the formation of a mixture of products

know the general formula for alkenes

know that alkenes and cycloalkenes are unsaturated hydrocarbons

understand the bonding in alkenes in terms of σ- and π- bonds

know what is meant by the term ‘electrophile’

understand the addition reactions of alkenes with:

i) hydrogen, in the presence of a nickel catalyst, to form an alkane
Knowledge of the application of this reaction to the manufacture of margarine by catalytic hydrogenation of unsaturated vegetable oils is expected.
ii) halogens to produce dihalogenoalkanes
iii) hydrogen halides to produce halogenoalkanes
iv) steam, in the presence of an acid catalyst, to produce alcohols
v) potassium manganate(VII), in acid conditions, to oxidise the double bond and produce a diol

understand that heterolytic bond fission of a covalent bond results in the formation of ions

understand the mechanism of the electrophilic addition reactions between alkenes and:

i) halogens
ii) hydrogen halides, including addition to unsymmetrical alkenes
iii) other given binary compounds

Use of the curly arrow notation is expected − curly arrows should start from either a bond or from a lone pair of electrons.
Knowledge of the relative stability of primary, secondary and tertiary carbocation intermediates is expected.

know the qualitative test for a C=C double bond using bromine or bromine water

know that alkenes form polymers through addition polymerisation

Be able to identify the repeat unit of an addition polymer given the monomer, and vice versa.

know that waste polymers can be separated into specific types of polymer for:

i) recycling
ii) incineration to release energy
iii) use as a feedstock for cracking

understand, in terms of the use of energy and resources over the life cycle of polymer products, that chemists can contribute to the more sustainable use of materials

understand how chemists limit the problems caused by polymer disposal by:

i) developing biodegradable polymers
ii) removing toxic waste gases caused by incineration of plastics

know that halogenoalkanes can be classified as primary, secondary or tertiary

understand what is meant by the term ‘nucleophile’

understand the reactions of halogenoalkanes with:

i) aqueous potassium hydroxide to produce alcohols (where the hydroxide ion acts as a nucleophile)
ii) aqueous silver nitrate in ethanol (where water acts as a nucleophile)
iii) potassium cyanide to produce nitriles (where the cyanide ion acts as a nucleophile)
Students should know this as an example of increasing the length of the carbon chain.
iv) ammonia to produce primary amines (where the ammonia molecule acts as a nucleophile)
v) ethanolic potassium hydroxide to produce alkenes (where the hydroxide ion acts as a base)

understand that experimental observations and data can be used to compare the relative rates of hydrolysis of:

i) primary, secondary and tertiary halogenoalkanes
ii) chloro-, bromo-, and iodoalkanes using aqueous silver nitrate in ethanol

CORE PRACTICAL 4: Investigation of the rates of hydrolysis of some halogenoalkanes

know the trend in reactivity of primary, secondary and tertiary halogenoalkanes

understand, in terms of bond enthalpy, the trend in reactivity of chloro-, bromo-, and iodoalkanes

understand the mechanisms of the nucleophilic substitution reactions between primary halogenoalkanes and:

i) aqueous potassium hydroxide
ii) ammonia

know that alcohols can be classified as primary, secondary or tertiary

understand the reactions of alcohols with:

i) oxygen in air (combustion)
ii) halogenating agents:
- PCl₅ to produce chloroalkanes
- 50% concentrated sulfuric acid and potassium bromide to produce bromoalkanes
- red phosphorus and iodine to produce iodoalkanes
iii) potassium dichromate(VI) in dilute sulfuric acid to oxidise primary alcohols to aldehydes (including a test for the aldehyde using Benedict’s/Fehling’s solution) and carboxylic acids, and secondary alcohols to ketones
In equations, the oxidising agent can be represented as [O].
iv) concentrated phosphoric acid to form alkenes by elimination
Descriptions of the mechanisms of these reactions are not expected.

understand the following techniques used in the preparation and purification of a liquid organic compound:

i) heating under reflux
ii) extraction with a solvent in a separating funnel
iii) distillation
iv) drying with an anhydrous salt
v) boiling temperature determination

CORE PRACTICAL 5: The oxidation of ethanol

CORE PRACTICAL 6: Chlorination of 2-methylpropan-2-ol using concentrated hydrochloric acid