Compound P contains several functional groups. [Figure of Compound P: a benzene ring attached to a C=C double bond. One carbon of the C=C is bonded to H and Cl, and also to the benzene ring. The other carbon of the C=C is bonded to two CN groups.]

Mark scheme

Marking points from the official mark scheme (Oct/Nov 2017). The mark or mark type is shown in brackets.

1. [2] nitrile; alkene; chloro; benzene/arene
2. [1] [Diagram of polymer with two repeat units, showing the C=C bond opened and the side groups (Cl, CN, phenyl) remaining]
3. [1] addition (polymerisation)
4. [1] Structure for excess Br₂(aq): Phenyl-C(Cl)(Br)-C(Br)(CN)(CN) where the C=C is saturated with Br atoms.
5. [1] type of organic reaction: (electrophilic) addition
6. [1] Structure for excess hot, conc., acidified MnO₄(aq): Benzoic acid (C₆H₅-COOH) and ethanedioic acid (HOOC-COOH).
7. [1] type of organic reaction: oxidation
8. [1] Structure for excess hot HCl(aq): Benzene ring-C(Cl)=C(COOH)COOH (nitrile groups hydrolysed to carboxylic acids).
9. [1] type of organic reaction: hydrolysis
10. [1] Structure for excess H₂/Pt catalyst: Cyclohexane ring with a Cl attached, and a -CH₂-CH(CH₂NH₂)(CH₂NH₂) side chain (benzene ring reduced, alkene reduced, nitriles reduced).
11. [1] type of organic reaction: reduction/hydrogenation