Questions set on this topic may require the application of knowledge covered in unit 2; specifically the rules for nomenclature and the ideas of isomerism, bond polarity, bond enthalpy and reaction types, including reagents and conditions.
4.5a Further ideas in organic chemistry
Students should be able to:
(i) apply the concept of functional groups to the range of organic compounds found in units
2 and 4
(ii) recognise and predict the existence of structural isomers within the types of organic
compound found in Units 2 and 4
(iii) recognise stereoisomerism as geometrical (cis-trans) or optical
(iv) explain the existence of geometrical (cis-trans) isomerism resulting from restricted
rotation about a carbon-carbon double bond
(v) understand the existence of optical isomerism resulting from a chiral centre in
molecules with a single asymmetric carbon atom, and understand optical isomers as
object and non-superimposable mirror images
(vi) recall optical activity as the ability of a single optical isomer to rotate the plane of
polarisation of plane polarised monochromatic light and understand the nature of a
racemic mixture.
4.5b Further reactions of organic compounds
Students should be able to recall, in terms of reagents and general reaction conditions, the
following reactions and classify reactions in this topic as oxidation, reduction,
condensation, nucleophilic
substitution or nucleophilic addition:
(i) halogeno-compounds with magnesium to form Grignard reagents and the reactions of
the latter with water, carbon dioxide and carbonyl compounds
· recall that Grignard reagents act as nucleophiles
· understand that the intermediate in these reactions needs to be decomposed by the
addition of acid
(ii) carboxylic acids with alcohols, lithium tetrahydridoaluminate(III) (lithium aluminium
hydride), phosphorus pentachloride, sodium carbonate and sodium hydrogencarbonate
· to include the formation of polyesters
(iii) esters with acids and alkalis
· to include the reversible nature of reactions with acids
(iv) carbonyl compounds with hydrogen cyanide, 2,4-dinitrophenylhydrazine, alkaline
ammoniacal silver nitrate solution, Fehling’s solution, iodine in the presence of alkali
(or potassium iodide and sodium chlorate(I)), sodium
tetrahydridoborate(III) (sodium borohydride) and lithium tetrahydridoaluminate(III) (lithium aluminium hydride)
(v) ethanoyl chloride with water, alcohols, ammonia and primary amines
(vi) primary amines with aqueous hydrogen ions, acid chlorides
· to include the formation of polyamides
(vii) nitriles undergoing hydrolysis and undergoing reduction
(viii) amides with phosphorus(V) oxide and bromine in aqueous alkali
(ix) amino acids with acids and bases, and their zwitterion structures.
· detailed knowledge of the buffering action of amino acids will not be expected