Compound 1.1 undergoes a substitution reaction to form Compounds 1.2 and 1.3: Br CH3 H;CO CH, 1.1 R1.1 Reaction number R1.2 CH; SUGUST Table Reaction conditions for Compound 1.1 and yield of products (Compounds 1.2 and 1.3). SHO Reaction conditions NaOCH3, methanol 1.2 methanol teroochomir S! AASIAN ------------ Ste CH; 1.2 0 H₂C OCH; 50 1.3 CH3 Product Yield/% 1.3 100 50 b. (6 marks) Based on the product yield information in Table 1.1, what are the most likely reaction mechanisms for reactions R1.1 and R1.2? Give reasoning for your assignment (two sentences for each reaction). c. (6 marks) Draw a curly arrow mechanism, for the formation of Compound 1.3 from Compound 1.1 in R1.1, including any transition state or intermediate. d. (4 marks) From individual solutions of the product(s) in R1.1 and R1.2 predict if these solutions would rotate plane-polarised light. Give your reasoning (two sentences only).

Fig: 1