2. a. Compound D, Figure 5, can undergo a palladium catalysed cyclisation to give compound E. BugSn Ph OTf Pd(PPh3)4 C25H26 LiCl E D Figure 5 (i) Name the reaction generating compound E from compound D. (ii) Discuss the catalytic cycle for the formation of compound E. (iii) Briefly explain the role of the LiCl additive in Figure 5. (iv) Draw the structure of compound E. [ [ Co

4. (a) (i) Draw the mechanism with three-dimensional conformations and identify the product for the solvolysis (SN1) reaction between compound (A) and acetic acid (CH3CO₂H). Me (A) OTS H (B) OTS (ii) Predict, with reasoning, whether compound (A) or compound (B) will undergo solvolysis faster.

Predict the major products of each of the following reactions. (a) (b) CI CI Br. (CH),COK NaBr ? DMSO ? DMF

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6. a) The structural formulae of three isomers are shown below. - -CH2CH, CHO A OCH₂CCH3 B C-CH₂CH3 C With the aid of equations, describe the reactions of the isomers with i) Hydrazine, NH₂NH2 ii) lodine in an alkaline solution iii) Ammoniacal silver nitrate b) With the aid of equations, state the reagents and conditions required to prepare i) B from 1-phenylpropan-2-ol ii) C from benzene

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2. (a) Reaction of an alkene with ozone followed by an oxidative workup gives the product shown. What is the structure of alkene A? A (b) Compounds B and C both have the formula C10H16. Hydrogenation of either compound over Pt gives the same product, cis-1-isopropyl-4-methylcyclohexane. Ozonolysis with reductive workup fragments the two compounds differently, as shown below. What are the structures of C B and C? (CHCl3, chloroform, is the solvent.) B 1) 03, CHCI 3 2) (CH3)2S 1) 03, CHC13 2) (CH3)2S H O 1) 03 2) H₂O2, H₂O H3C- H O CH3 3. (a) Draw the structures of all enols that would spontaneously form this ketone, including stereoisomers. + + I HO₂C H + La CH3CH₂-C-CH(CH3)2 O= (b) Would alkyne hydration be a good preparative method for this compound? If so, give the reaction. If not, explain why.

The natural product halomon could theoretically arise from another naturally occurring compound known as myrcene. To accomplish this, a biochemical process that could deliver the synthetic equivalent of BrCi to all three double bonds would be required. (Chem Comm. 2014, 50, 13725) (a) Using three molar equivalents of BrCL please provide a mechanism to account for the formation of the bracketed structure (you do not need to show stereochemistry in this mechanism) HB (3 equiv) myrcene balomon 8.61a Add curved arrow(s) to show the mechanism steps. Edit Drawing sits

(c) Compound 2F shown below is a tetra-substituted cyclooctatetraene. After heating 2F at 160 degree for 6 hours, researchers observed the formation of an isomer of 2F. Draw the isomer structure and provide a plausible mechanism to explain the formation of the isomers. 2F

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