Which compound, on reaction with hydrogen cyanide, produces a compound with a chiral centre?

13.2.1.1 homologous series

13.2.1.2 saturated and unsaturated

13.2.1.3 homolytic and heterolytic fission

13.2.1.4 free radical, initiation, propagation, termination (the use of arrows to show movement of single electrons is not required)

13.2.1.5 nucleophile, electrophile, nucleophilic, electrophilic

13.2.1.6 addition, substitution, elimination, hydrolysis, condensation

13.2.1.7 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] one atom of hydrogen from a reducing agent)

13.2.2.1 free-radical substitution

13.2.2.2 electrophilic addition

13.2.2.3 nucleophilic substitution

13.2.2.4 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)

17.1.1.1 the oxidation of primary alcohols using acidified and distillation to produce aldehydes

17.1.1.2 the oxidation of secondary alcohols using acidified or acidified and distillation to produce ketones

17.1.2.1 the reduction of aldehydes and ketones, using to produce alcohols

17.1.2.2 the reaction of aldehydes and ketones with HCN, KCN as catalyst, and heat to produce hydroxynitriles exemplified by ethanal and propanone

17.1.3 describe the mechanism of the nucleophilic addition reactions of hydrogen cyanide with aldehydes and ketones in 17.1.2(b)

17.1.4 describe the use of 2,4-dinitrophenylhydrazine (2,4-DNPH reagent) to detect the presence of carbonyl compounds

17.1.5 deduce the nature (aldehyde or ketone) of an unknown carbonyl compound from the results of simple tests (Fehling’s and Tollens’ reagents; ease of oxidation)

17.1.6 deduce the presence of a – group in an aldehyde or ketone, , from its reaction with alkaline (aq) to form a yellow precipitate of tri-iodomethane and an ion,