Specification
Module 4
reference
Basic concepts of organic chemistry
Can you apply IUPAC rules of nomenclature for systematically naming
4.1.1 a
organic compounds?
Can you interpret and use the term general formula (the simplest algebraic
4.1.1 b i
formula of a member of a homologous series)?
Can you interpret and use the term structural formula (the minimal detail
4.1.1 b ii
that shows the arrangement of atoms in a molecule)?
Can you interpret and use the term displayed formula (the relative
4.1.1 b iii
positioning of atoms and the bonds between them)?
Can you interpret and use the term skeletal formula (the simplified organic
4.1.1 b iv formula, shown by removing hydrogen atoms from alkyl chains, leaving
just a carbon skeleton and associated functional groups)?
Can you interpret and use the term homologous series (a series of organic
4.1.1 c i compounds having the same functional group but with each successive
member differing by CH2)?
Can you interpret and use the term functional group (a group of atoms
4.1.1 c ii
responsible for the characteristic reactions of a compound)?
4.1.1 c iii Can you interpret and use the term alkyl group (formula CnH2n+1)?
Can you interpret and use the term aliphatic (a compound containing
4.1.1 c iv carbon and hydrogen joined together in straight chains, branched chains
or non-aromatic rings)?
Can you interpret and use the term alicyclic (an aliphatic compound
4.1.1 c v
arranged in non-aromatic rings with or without side chains)?
Can you interpret and use the term aromatic (a compound containing a
4.1.1 c vi
benzene ring)?
Can you interpret and use the term saturated (single carbon–carbon
4.1.1 c vii bonds only) and unsaturated (the presence of multiple carbon–carbon
bonds, including C=C, C≡C and aromatic rings)?
Can you use the general formula of a homologous series to predict the
4.1.1 d
formula of any member of the series?
Specification
Module 4
reference
Can you explain the term structural isomers (compounds with the same
molecular formula but different structural formulae) and determine
4.1.1 e
possible structural formulae of an organic molecule, given its molecular
formula?
Can you describe homolytic fission (in terms of each bonding atom
4.1.1 f i
receiving one electron from the bonded pair, forming two radicals)?
Can you describe heterolytic fission (in terms of one bonding atom
4.1.1 f ii
receiving both electrons from the bonded pair)?
Can you describe the term radical (a species with an unpaired electron)
4.1.1 g
and use of ‘dots’ to represent species that are radicals in mechanisms?
Can you explain a ‘curly arrow’ described as the movement of an electron
4.1.1 h
pair, showing either heterolytic fission or formation of a covalent bond?
Can you describe reaction mechanisms, using diagrams, to show clearly
4.1.1 i
the movement of an electron pair with ‘curly arrows’ and relevant dipoles?
Alkanes
Can you describe alkanes as saturated hydrocarbons containing single
4.1.2 a C–C and C–H bonds as σ-bonds (overlap of orbitals directly between the
bonding atoms), with free rotation of the σ-bond?
Can you explain the tetrahedral shape and bond angle around each
4.1.2 b
carbon atom in alkanes in terms of electron pair repulsion?
Can you explain the variations in boiling points of alkanes with different
4.1.2 c carbon-chain length and branching, in terms of induced dipole–dipole
interactions (London forces)?
Can you describe the low reactivity of alkanes with many reagents in
4.1.2 d terms of the high bond enthalpy and very low polarity of the σ-bonds
present?
Can you describe complete combustion of alkanes, as used in fuels, and
4.1.2 e the incomplete combustion of alkane fuels in a limited supply of oxygen
with the resulting potential dangers from CO?
Specification
Module 4
reference
Can you describe the reaction of alkanes with chlorine and bromine by
radical substitution using ultraviolet radiation, including a mechanism
4.1.2 f
involving homolytic fission and radical reactions in terms of initiation,
propagation and termination?
Can you describe the limitations of radical substitution in synthesis by the
4.1.2 g formation of a mixture of organic products, in terms of further substitution
and reactions at different positions in a carbon chain?
Alkenes
Can you describe alkenes as unsaturated hydrocarbons containing a C=C
bond comprising a π-bond (sideways overlap of adjacent p-orbitals above
4.1.3 a
and below the bonding C atoms) and a σ-bond (overlap of orbitals directly
between the bonding atoms); with restricted rotation of the π-bond?
Can you explain the trigonal planar shape and bond angle around each
4.1.3 b
carbon in the C=C of alkenes in terms of electron pair repulsion?
Can you explain the term stereoisomers (compounds with the same
4.1.3 c i
structural formula but with a different arrangement in space)?
Can you explain the term E/Z isomerism (an example of stereoisomerism,
in terms of restricted rotation about a double bond and the requirement for
4.1.3 c i
two different groups to be attached to each carbon atom of the C=C
group)?
Can you explain the term cis–trans isomerism (a special case of E/Z
4.1.3 c i isomerism in which two of the substituent groups attached to each carbon
atom of the C=C group are the same)?
Can you use Cahn–Ingold–Prelog (CIP) priority rules to identify the E and
4.1.3 c ii
Z stereoisomers?
Can you determine possible E/Z or cis–trans stereoisomers of an organic
4.1.3 d
molecule, given its structural formula?
Can you describe the reactivity of alkenes in terms of the relatively low
4.1.3 e
bond enthalpy of the π-bond?
Can you describe addition reactions of alkenes with: hydrogen in the
4.1.3 f i
presence of a suitable catalyst (e.g. Ni) to form alkanes?
Specification
Module 4
reference
Can you describe addition reactions of alkenes with halogens to form
4.1.3 f ii dihaloalkanes, including the use of bromine to detect the presence of a
double C=C bond as a test for unsaturation in a carbon chain?
Can you describe addition reactions of alkenes with hydrogen halides to
4.1.3 f iii
form haloalkanes?
Can you describe addition reactions of alkenes with steam in the presence
4.1.3 f iv
of an acid catalyst (e.g. H3PO4) to form alcohols?
4.1.3 g Can you define and use the term electrophile (an electron pair acceptor)?
Can you explain the mechanism of electrophilic addition in alkenes by
4.1.3 h
heterolytic fission?
Can you use Markownikoff’s rule to predict formation of a major organic
product in addition reactions of H–X to unsymmetrical alkenes (e.g. H–Br
4.1.3 i
to propene) in terms of the relative stabilities of carbocation intermediates
in the mechanism?
Can you describe addition polymerisation of alkenes and substituted
4.1.3 j i alkenes, including the repeat unit of an addition polymer deduced from a
given monomer?
Can you describe addition polymerisation of alkenes and substituted
4.1.3 j ii alkenes, including identification of the monomer that would produce a
given section of an addition polymer?
Can you list and describe the benefits for sustainability of processing
4.1.3 k i
waste polymers by combustion for energy production?
Can you list and describe the benefits for sustainability of processing
4.1.3 k ii waste polymers by use as an organic feedstock for the production of
plastics and other organic chemicals?
Can you list and describe the benefits for sustainability of processing
4.1.3 k iii waste polymers by removal of toxic waste products formed during disposal
by combustion of halogenated plastics (e.g. PVC)?
Can you list and describe benefits to the environment of development of
4.1.3 l
biodegradable and photodegradable polymers?
Specification
Module 4
reference
Alcohols
Can you describe the polarity of alcohols and explain, in terms of
4.2.1 a i hydrogen bonding, the water solubility and the relatively low volatility of
alcohols compared with alkanes?
4.2.1 a ii Can you classify alcohols into primary, secondary and tertiary alcohols?
4.2.1 b Can you explain combustion of alcohols?
Can you explain oxidation of alcohols by an oxidising agent
(e.g. Cr2O72–/H+), including the oxidation of primary alcohols to form
4.2.1 c i
aldehydes and carboxylic acids; and the control of the oxidation product
using different reaction conditions?
Can you explain oxidation of alcohols by an oxidising agent
4.2.1 c ii (e.g. Cr2O72–/H+), including the oxidation of secondary alcohols to form
ketones?
Can you explain oxidation of alcohols by an oxidising agent
4.2.1 c iii (e.g. Cr2O72–/H+), including the resistance to oxidation of tertiary
alcohols?
Can perform an experiment in which you eliminate H2O from alcohols in
4.2.1 d the presence of an acid catalyst (e.g. H3PO4 or H2SO4) and heat to form
alkenes?
Can perform an experiment in which you substitute with halide ions in the
4.2.1 e
presence of acid (e.g. NaBr/H2SO4) to form haloalkanes?
Haloalkanes
Can you describe hydrolysis of haloalkanes in a substitution reaction by
4.2.2 a i
aqueous alkali?
Can you describe hydrolysis of haloalkanes in a substitution reaction by
4.2.2 a ii water in the presence of AgNO3 and ethanol to compare experimentally
the rates of hydrolysis of different carbon–halogen bonds?
4.2.2 b Can you define and use of the term nucleophile (an electron pair donor)?
Specification
Module 4
reference
Can you describe the mechanism of nucleophilic substitution in the
4.2.2 c
hydrolysis of primary haloalkanes with aqueous alkali?
Can you explain the trend in the rates of hydrolysis of primary haloalkanes
4.2.2 d in terms of the bond enthalpies of carbon–halogen bonds (C–F, C–Cl, C–
Br and C–I)?
Can you explain the production of halogen radicals by the action of
ultraviolet (UV) radiation on CFCs in the upper atmosphere and the
4.2.2 e i
resulting catalysed breakdown of the Earth’s protective ozone layer,
including equations to represent the production of halogen radicals?
Can you explain the production of halogen radicals by the action of
ultraviolet (UV) radiation on CFCs in the upper atmosphere and the
4.2.2 e ii resulting catalysed breakdown of the Earth’s protective ozone layer,
including equations to represent the catalysed breakdown of ozone by Cl•
and other radicals (e.g. •NO)?
Organic synthesis
Can you list and describe the techniques and procedures for use of
4.2.3 a i
Quickfit apparatus including for distillation and heating under reflux?
Can you describe preparation and purification of an organic liquid
4.2.3 a ii including the use of a separating funnel to remove an organic layer from
an aqueous layer?
Can you describe preparation and purification of an organic liquid
including drying with an anhydrous salt (e.g. MgSO4, CaCl2)?
4.2.3 a ii
Can you describe preparation and purification of an organic liquid
4.2.3 a ii
including redistillation?
Can you describe an organic molecule containing several functional group
4.2.3 b i
identification of individual functional groups
Can you describe an organic molecule containing several functional
4.2.3 b ii
groups prediction of properties and reactions
Can you describe an organic molecule containing several functional
4.2.3 c
groups two-stage synthetic routes for preparing organic compounds?
Specification
Module 4
reference
Spectroscopy
Can you describe how infrared (IR) radiation causes covalent bonds to
4.2.4 a
vibrate more and absorb energy?
Can you explain absorption of infrared radiation by atmospheric gases
4.2.4 b containing C=O, O–H and C–H bonds (e.g. H2O, CO2 and CH4), the
suspected link to global warming and resulting changes to energy usage?
Can you use an infrared spectrum of an organic compound to identify an
4.2.4 c i
alcohol from an absorption peak of the O–H bond?
Can you use an infrared spectrum of an organic compound to identify an
4.2.4 c ii
aldehyde or ketone from an absorption peak of the C=O bond?
Can you use an infrared spectrum of an organic compound to identify a
4.2.4 c iii carboxylic acid from an absorption peak of the C=O bond and a broad
absorption peak of the O–H bond?
Can you interpret and predict an infrared spectrum of familiar or unfamiliar
4.2.4 d
substances using supplied data?
Can you use infrared spectroscopy to monitor gases causing air pollution
4.2.4 e (e.g. CO and NO from car emissions) and in modern breathalysers to
measure ethanol in the breath?
Can you use a mass spectrum of an organic compound to identify the
4.2.4 f
molecular ion peak and hence to determine molecular mass?
Can you analyse fragmentation peaks in a mass spectrum to identify parts
4.2.4 g
of structures?
Can you deduce the structures of organic compounds from different
4.2.4 h i
analytical data including elemental analysis?
Can you deduce the structures of organic compounds from different
4.2.4 h ii
analytical data including mass spectra?
Can you deduce the structures of organic compounds from different
4.2.4 h iii
analytical data including IR spectra?
