Which compound has the greatest number of stereoisomers?

13.4.1 describe structural isomerism and its division into chain, positional and functional group isomerism

13.4.2 describe stereoisomerism and its division into geometrical (cis/trans) and optical isomerism (use of E, Z nomenclature is acceptable but is not required)

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

13.4.4 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)

13.4.5 identify chiral centres and geometrical (cis/trans) isomerism in a molecule of given structural formula including cyclic compounds

13.4.6 deduce the possible isomers for an organic molecule of known molecular formula

14.2.1.1 elimination of HX from a halogenoalkane by ethanolic NaOH and heat

14.2.1.2 dehydration of an alcohol, by using a heated catalyst

14.2.1.3 cracking of a longer chain alkane

14.2.2.1.1 hydrogen in a hydrogenation reaction, and Pt/Ni catalyst and heat

14.2.2.1.2 steam, catalyst

14.2.2.1.3 a hydrogen halide, HX(g) at room temperature

14.2.2.1.4 a halogen,

14.2.2.2 the oxidation by cold dilute acidified to form the diol

14.2.2.3 the oxidation by hot concentrated acidified leading to the rupture of the carbon–carbon double bond and the identities of the subsequent products to determine the position of alkene linkages in larger molecules

14.2.2.4 addition polymerisation exemplified by the reactions of ethene and propene

14.2.3 describe the use of aqueous bromine to show the presence of a C=C bond

14.2.4 describe the mechanism of electrophilic addition in alkenes, using bromine / ethene and hydrogen bromide / propene as examples

14.2.5 describe and explain the inductive effects of alkyl groups on the stability of primary, secondary and tertiary cations formed during electrophilic addition (this should be used to explain Markovnikov addition)