A-LevelChemistryPolymerisation9701/41 · Oct/Nov 2017 · Q512 Marks

Compound P contains several functional groups. [Figure of Compound P with a benzene ring attached to C(Cl)=C(CN)₂]

(a)Name the functional groups present in P.[2]
(b)Compound P can be polymerised. Draw a section of the polymer of P showing two repeat units. Name the type of polymerisation. type of polymerisation ..............................[2]
(c)Complete the following table to show the structures of the products formed and the type of organic reaction when P reacts with the four reagents.[8]

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Mark scheme

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

[2] (a) nitrile; alkene; chloro; benzene/arene
[1] (b) [diagram of polymer showing two repeat units: poly(phenyl-CH(Cl)-C(CN)2)]
[1] (b) addition (polymerisation)
[1] (c) reagent: excess Br₂(aq), structure of product: phenyl-C(Cl)(Br)-C(Br)(CN)₂, type of organic reaction: (electrophilic) addition
[1] (c) reagent: excess hot, conc. MnO₄(aq), structure of products: phenyl-COOH and HOOC-COOH and Cl-COOH, type of organic reaction: oxidation
[1] (c) reagent: excess hot HCl(aq), structure of product: phenyl-CH(Cl)=C(COOH)₂, type of organic reaction: hydrolysis
[1] (c) reagent: excess H₂/Pt catalyst, structure of product: cyclohexyl-CH₂(Cl)-CH₂(NH₂)-CH₂(NH₂), type of organic reaction: reduction/hydrogenation

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