1. Answer ALL parts (a) - (c). (a) Answer BOTH parts (i) and (ii) (i) Provide a mechanism for the reaction shown below accounting for the stereochemical outcome. COH NaNO2 CO2H NH2 HCI, H20 OH (6 marks) (ii) Provide a mechanism for the reaction shown below. Explain the observed selectivity using a conformational drawing. Ph Ph i) LDA (1 equiv.) Ph. 7 ii) PhCH2Br (6 marks) Question 1 continued on next page Question 1 continued (b) Answer BOTH parts (i) and (ii) (i) Provide a detailed mechanistic analysis of the reaction shown below. Include in your answer a mechanism, and discuss the observed selectivity using a conformational drawing. m-CPBA So.ph SO Ph SO Ph SO Ph major product 95:5 d.r. (6 marks) (ii) Predict the major product of the reaction shown below using the Felkin-Anh model. Include in your answer a mechanism, and account for any stereoselectivity you propose. i) PhMgBr H Ph + Ph Ph Phi Ph ii) H20 OH OH (6 marks) Question 1 continued on next page Question 1 continued (c) Propose a synthesis of the chiral ether below, using one of the auxiliaries shown. Include in your answer reagents for each synthetic step you propose. No mechanisms are required. multiple steps CI O HN HN HN O Ph 16 mauro