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Topic 10: Organic Chemistry

10.1 Fundamentals of Organic Chemistry
Essential Idea:
  • Organic chemistry focuses on the chemistry of compounds containing carbon.
  • A homologous series is a series of compounds of the same family, with the same general formula, which differ from each other by a common structural unit.
  • Structural formulas can be represented in full and condensed format.
  • Structural isomers are compounds with the same molecular formula but different arrangements of atoms.
  • Functional groups are the reactive parts of molecules.
  • Saturated compounds contain single bonds only and unsaturated compounds contain double or triple bonds.
  • Benzene is an aromatic, unsaturated hydrocarbon.
Applications & Skills:
  • Explanation of the trends in boiling points of members of a homologous series.
  • Distinction between empirical, molecular and structural formulas.
  • Identification of different classes: alkanes, alkenes, alkynes, halogenoalkanes, alcohols, ethers, aldehydes, ketones, esters, carboxylic acids, amines, amides, nitriles and arenes.
  • Identification of typical functional groups in molecules eg phenyl, hydroxyl, carbonyl, carboxyl, carboxamide, aldehyde, ester, ether, amine, nitrile, alkyl, alkenyl and alkynyl.
  • Construction of 3-D models (real or virtual) of organic molecules.
  • Application of IUPAC rules in the nomenclature of straight-chain and branched-chain isomers.
  • Identification of primary, secondary and tertiary carbon atoms in halogenoalkanes and alcohols and primary, secondary and tertiary nitrogen atoms in amines.
  • Discussion of the structure of benzene using physical and chemical evidence.
Nature of Science:
  • Serendipity and scientific discoveries—PTFE and superglue.
  • Ethical implications—drugs, additives and pesticides can have harmful effects on both people and the environment.
PPT: Fundamentals of Organic Chem
10.2 Functional Group Chemistry
Essential Idea:
  • Structure, bonding and chemical reactions involving functional group interconversions are key strands in organic chemistry.
  • Alkanes
    • Alkanes have low reactivity and undergo free-radical substitution reactions.
  • Alkenes:
    • Alkenes are more reactive than alkanes and undergo addition reactions. Bromine water can be used to distinguish between alkenes and alkanes.
  • Alcohols:
    • Alcohols undergo nucleophilic substitution reactions with acids (also called esterification or condensation) and some undergo oxidation reactions.
  • Halogenoalkanes:
    • Halogenoalkanes are more reactive than alkanes. They can undergo (nucleophilic) substitution reactions. A nucleophile is an electron-rich species containing a lone pair that it donates to an electron-deficient carbon.
  • Polymers:
    • Addition polymers consist of a wide range of monomers and form the basis of the plastics industry.
  • Benzene:
    • Benzene does not readily undergo addition reactions but does undergo electrophilic substitution reactions
Applications & Skills:
  • Alkanes:
    • Writing equations for the complete and incomplete combustion of hydrocarbons.
    • Explanation of the reaction of methane and ethane with halogens in terms of a free-radical substitution mechanism involving photochemical homolytic fission.
  • Alkenes:
    • Writing equations for the reactions of alkenes with hydrogen and halogens and of symmetrical alkenes with hydrogen halides and water.
    • Outline of the addition polymerization of alkenes.
    • Relationship between the structure of the monomer to the polymer and repeating unit.
  • Alcohols:
    • Writing equations for the complete combustion of alcohols.
    • Writing equations for the oxidation reactions of primary and secondary alcohols (using acidified potassium dichromate(VI) or potassium manganate(VII) as oxidizing agents). Explanation of distillation and reflux in the isolation of the aldehyde and carboxylic acid products.
    • Writing the equation for the condensation reaction of an alcohol with a carboxylic acid, in the presence of a catalyst (eg concentrated sulfuric acid) to form an ester.
  • Halogenoalkanes:
    • Writing the equation for the substitution reactions of halogenoalkanes with aqueous sodium hydroxide.
Nature of Science:
  • Use of data—much of the progress that has been made to date in the developments and applications of scientific research can be mapped back to key organic chemical reactions involving functional group interconversions.
PPT: Functional Group Chemistry