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13. An introduction to AS Level organic chemistry

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  1. AS organic chemistry conventions and functional group reference

    1. • Use the syllabus conventions X for a halogen atom and R/R' for alkyl groups or hydrogen as appropriate.

    2. • Recognise and use the AS organic functional groups and representations from the syllabus table. - (a) alkene: C=C bond - (b) halogenoalkane: halogen X; primary, secondary and tertiary halogenoalkanes - (c) alcohol: hydroxyl -OH; primary, secondary and tertiary alcohols - (d) aldehyde: carbonyl -CHO - (e) ketone: carbonyl >C=O - (f) carboxylic acid: carboxyl -COOH - (g) ester: ester -COO- - (h) primary amine: -NH2 - (i) nitrile: -CN

  2. 13.1 Formulas, functional groups and nomenclature

    1. • Define: hydrocarbon as a compound made up of C and H atoms only

    2. • Understand: alkanes are simple hydrocarbons with no functional group

    3. • Understand: the compounds in the table on pages 29 and 30 contain a functional group which dictates their physical/chemical properties

    4. • Interpret/use: the general, structural, displayed and skeletal formulas of the classes of compound stated in the table on pages 29 and 30

    5. • Understand and use systematic nomenclature of simple aliphatic organic molecules with functional groups detailed in the table on pages 29 and 30, up to six carbon atoms (six plus six for esters, straight chains only for esters and nitriles)

    6. • Deduce the molecular and/or empirical formula of a compound, given its structural, displayed or skeletal formula

  3. 13.2 Characteristic organic reactions

    1. • Interpret/use: the following terminology associated with types of organic compounds and reactions: - (a) homologous series - (b) saturated and unsaturated - (c) homolytic and heterolytic fission - (d) free radical, initiation, propagation, termination - (e) nucleophile, electrophile, nucleophilic, electrophilic - (f) addition, substitution, elimination, hydrolysis, condensation - (g) oxidation and reduction (in equations for organic redox reactions, the symbol [O] can be used to represent one atom of oxygen - from an oxidising agent and the symbol [H] to represent one atom of hydrogen from a reducing agent)

    2. • Understand and use the following terminology associated with types of organic mechanisms: - (a) free-radical substitution - (b) electrophilic addition - (c) nucleophilic substitution - (d) nucleophilic addition (in organic reaction mechanisms, the use of curly arrows to represent movement of electron pairs is expected; the arrow should begin at a bond or a lone pair of electrons)

  4. 13.3 Shapes of organic molecules; σ and π bonds

    1. 13.3.1Organic molecules as either straight-chained,

      • Describe organic molecules as either straight-chained, branched or cyclic

    2. 13.3.2Shape of, and bond angles in, molecules

      • Describe/explain: the shape of, and bond angles in, molecules containing sp, sp 2 and sp3 hybridised atoms

    3. 13.3.3Arrangement of σ and π bonds in molecules

      • Describe the arrangement of σ and π bonds in molecules containing sp, sp2 and sp3 hybridised atoms

    4. 13.3.4Terms: planar when describing the arrangement

      • Use terms: planar when describing the arrangement of atoms in organic molecules, e.g. ethene

  5. 13.4 Structural isomerism and stereoisomerism

    1. • Describe structural isomerism and its division into chain, positional and functional group isomerism

    2. • Describe stereoisomerism and its division into geometrical (cis/trans) and optical isomerism (use of E/Z nomenclature is acceptable but is not required)

    3. • Describe geometrical (cis/trans) isomerism in alkenes, and explain its origin in terms of restricted rotation due to the presence of π bonds

    4. • Explain what is meant by a chiral centre and that such a centre gives rise to two optical isomers (enantiomers) (Candidates should appreciate that compounds can contain more than one chiral centre, but knowledge of meso compounds, or nomenclature such as diastereoisomers is not required.)

    5. • Identify chiral centres and geometrical (cis/trans) isomerism in a molecule of given structural formula, including cyclic compounds

    6. • Deduce the possible isomers for an organic molecule of known molecular formula