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11. Organic chemistry

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  1. 11.1 Formulae, functional groups and terminology

    1. • Draw and interpret the displayed formula of a molecule to show all the atoms and all the bonds

    2. • Write and interpret general formulae of compounds in the same homologous series, (a) alkanes, C nH2n+2 (b) alkenes, CnH2n (c) alcohols, C nH2n+1OH (d) carboxylic acids, CnH2n+1COOH

    3. • Identify a functional group as an atom or group of atoms that determine the chemical properties of a homologous series

    4. • State: a structural formula is an unambiguous description of the way the atoms in a molecule are arranged, including CH 2=CH2, CH3CH2OH, CH3COOCH3

    5. • Define structural isomers as compounds with the same molecular formula, but different structural formulae, including C4H10 as CH3CH2CH2CH3 and CH3CH(CH3)CH3 and C4H8 as CH3CH2CH=CH2 and CH3CH=CHCH3

    6. • State: a homologous series is a family of similar compounds with similar chemical properties due to the presence of the same functional group

    7. • State: a saturated compound has molecules in which all carbon–carbon bonds are single bonds

    8. • State: an unsaturated compound has molecules in which one or more carbon– carbon bonds are not single bonds

    9. • Describe homologous series features: same functional group and general formula, adjacent members differ by -CH2-, physical properties show trends, chemical properties are similar

  2. 11.2 Naming organic compounds

    1. • Name and draw the displayed formulae of: (a) methane and ethane (b) ethene (c) ethanol (d) ethanoic acid (e) the products of the reactions stated in sections 11.4–11.7

    2. • State the type of compound present, given a chemical name ending in -ane, -ene, -ol, or -oic acid or from a molecular formula or displayed formula

    3. • Name/draw structural and displayed formulae of unbranched alkanes, alkenes (including but-1-ene/but-2-ene), alcohols (propan-1-ol/propan-2-ol/butan-1-ol/butan-2-ol) and carboxylic acids up to four carbons

    4. • Name and draw the displayed formulae of the unbranched esters which can be made from unbranched alcohols and carboxylic acids, each containing up to four carbon atoms

  3. 11.3 Fuels

    1. • Name the fossil fuels: coal, natural gas and petroleum

    2. • Name methane as the main constituent of natural gas

    3. • State: hydrocarbons are compounds that contain hydrogen and carbon only

    4. • State: petroleum is a mixture of hydrocarbons

    5. • Describe separation of petroleum into useful fractions by fractional distillation

    6. • Describe petroleum fraction trends up the column: shorter chains, higher volatility, lower boiling points and lower viscosity

    7. • Name fraction uses: refinery gas for heating/cooking; gasoline/petrol for cars; naphtha feedstock; kerosene/paraffin jet fuel; diesel oil/gas oil for diesel engines; fuel oil for ships/home heating; lubricating oil for lubricants/waxes/polishes; bitumen for roads

  4. 11.4 Alkanes

    1. • State: the bonding in alkanes is single covalent and that alkanes are saturated hydrocarbons

    2. • Describe properties of alkanes as being generally unreactive, except in terms of combustion and substitution by chlorine

    3. • State: in a substitution reaction one atom or group of atoms is replaced by another atom or group of atoms

    4. • Describe substitution reaction of alkanes with chlorine as a photochemical reaction, with ultraviolet light providing the activation energy, Ea, and draw the structural or displayed formulae of the products, limited to monosubstitution

  5. 11.5 Alkenes

    1. • State: the bonding in alkenes includes a double carbon–carbon covalent bond and that alkenes are unsaturated hydrocarbons

    2. • Describe manufacture of alkenes and hydrogen by the cracking of larger alkane molecules using a high temperature and a catalyst

    3. • Describe reasons for the cracking of larger alkane molecules

    4. • Describe test to distinguish between saturated and unsaturated hydrocarbons by their reaction with aqueous bromine

    5. • State: in an addition reaction only one product is formed

    6. • Describe alkene addition reactions with bromine/aqueous bromine, hydrogen with nickel catalyst, and steam with acid catalyst; draw structural/displayed formulae of products

  6. 11.6 Alcohols

    1. • Describe ethanol manufacture by: (a) fermentation of aqueous glucose at 25-35 °C with yeast and no oxygen (b) catalytic steam addition to ethene at 300 °C and 6000 kPa/60 atm with acid catalyst

    2. • Describe combustion of ethanol

    3. • State the uses of ethanol as: (a) a solvent (b) a fuel

    4. • Describe advantages and disadvantages of the manufacture of ethanol by: (a) fermentation (b) catalytic addition of steam to ethene

  7. 11.7 Carboxylic acids

    1. 11.7.1Reaction of ethanoic acid

      • Describe reaction of ethanoic acid with: (a) metals (b) bases (c) carbonates including names and formulae of the salts produced

    2. 11.7.2Formation of ethanoic acid by the

      • Describe formation of ethanoic acid by the oxidation of ethanol: (a) with acidified aqueous potassium manganate(VII) (b) by bacterial oxidation during vinegar production

    3. 11.7.3Reaction of a carboxylic acid with an

      • Describe reaction of a carboxylic acid with an alcohol using an acid catalyst to form an ester

  8. 11.8 Polymers

    1. • Define polymers as large molecules built up from many smaller molecules called monomers

    2. • Describe formation of poly(ethene) as an example of addition polymerisation using ethene monomers

    3. • State: plastics are made from polymers

    4. • Describe how the properties of plastics have implications for their disposal

    5. • Describe environmental challenges caused by plastics, (a) disposal in landfill sites (b) accumulation in oceans (c) formation of toxic gases from burning

    6. • Identify the repeat units and/or linkages in addition polymers and in condensation polymers

    7. • Deduce the structure or repeat unit of an addition polymer from a given alkene and vice versa

    8. • Deduce the structure or repeat unit of a condensation polymer from given monomers and vice versa, (a) polyamides from a dicarboxylic acid and a diamine (b) polyesters from a dicarboxylic acid and a diol

    9. • Describe differences between addition and condensation polymerisation

    10. • Describe and draw the structure of: (a) nylon, a polyamide C O C O C C OO N H N H N H N H (b) PET, a polyester C O C O C C OO O OO O The full name for PET, polyethylene terephthalate, is not required

    11. • State: PET can be converted back into monomers and re-polymerised

    12. • Describe proteins as natural polyamides and that they are formed from amino acid monomers with the general structure: H O H OH N H C C R where R represents different types of side- chain

    13. • Describe and draw the structure of proteins as: N H C O N H C O N H C O