A-LevelChemistryPolymerisation9701/42 · Feb/Mar 2019 · Q511 Marks
Methyl 2-cyanoprop-2-enoate, W, is the major component of Super Glue, a rapid-setting adhesive. As the adhesive sets, the monomer W polymerises. [Figure 5.1]
- (a)(i)Draw a section of the polymer showing two repeat units.[2]
- (a)(ii)Name the type of polymerisation occurring.[1]
- (a)(iii)Suggest two types of intermolecular force that could occur between the Super Glue polymer and the objects glued together. For each type of intermolecular force, refer to the atoms/groups in the Super Glue polymer involved in the attraction.[2]
- (b)(i)Suggest the identities of compounds Y and Z by drawing their structures in the boxes.[2]
- (b)(ii)Suggest suitable reagents and conditions for each of the steps 1–3. step 1 step 2 step 3[4]
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Mark scheme
Marking points from the official mark scheme (Feb/Mar 2019). The mark or mark type is shown in brackets.
- [2] M1 correct C-C backbone (with correct side groups)
- M2 continuation bonds and two repeat units
- [1] addition
- [2] Any two of: permanent dipole (attraction): C, N, O, OR CO, CN, CO₂CH₃, OCH₃
- H-bonding: N, O OR CO, CN
- London/van der Waals: N, C, H, O OR CH₃, CN, CO₂CH₃, C–C chains
- [2] Y CH₃COCO₂CH₃
- Z CH₃C(OH)(CN)CO₂CH₃
- [4] M1/M2 step 1: CH₃OH and (conc) H₂SO₄ + heat
- M3 step 2: HCN + NaCN catalyst
- M4 step 3: T > 100°C / heat with Al₂O₃ (or heat with c. H₂SO₄)
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