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Me Br Me OEt 'O OEt | Not NNT ON 12 13 This question relates to the radical cyclisation reaction shown below. When the substrate

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Me Br Me OEt 'O OEt | Not NNT ON 12 13 This question relates to the radical cyclisation reaction shown below. When the substrate 12 is treated with azobisisobutyronitrile (AIBN), in the presence of stoichiometric tributyltin hydride (BuSn1), compound 13 is isolated as the major product BU SAH AIBN benzene, C12H202 NC 14 AIBN major product minor product Answer ALL parts (1)-(vi). (0) Provide a full reaction mechanism for the thermal decomposition of AIBN to produce the initiating species. 2 marks (ii) Show how the major product 13 is produced by completing the full reaction mechanism. 6 marks (ii) Which species "carries the chain" during the propagation steps of the reaction pathway? 1 mark (iv) Give the structure of the minor product 14 using mechanistic diagrams to show how it is formed. Note: 14 does not contain an alkene functional group. 2 marks (v) is the major product 13 the thermodynamic or kinetic product? 1 mark (vi) Explain why 13 is formed as the major product and 14 is formed as the minor product using thermodynamic and/or kinetic reasoning. 2 marks

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