PRINT NAME: CHEM 231 Exam 2 Example Dr. Bebbington 1) Rank the following acids in order of acidity (1 = most acidic, 4 = least acidic) (5 points) Explain your answer: (3 points) 2) Give mechanisms for the following transformations (5 points each): (15 points) 3) Name the following molecules: (12 points) 4) Fill in the products of the following reactions (3 points each): 5) i) Explain why epoxides are much more reactive to ring-opening than other cyclic ethers (Hint: consider why epoxide C-O bonds are weaker than usual C-O bonds): (3 points) ii) Below are two acid-catalyzed epoxide ring-opening reactions: In one case, the epoxide attacks the terminal end of the epoxide, and in the other, it attacks the more substituted side. Explain why this is: (6 points) Q5 continues over page… iii) The reaction below produces two products: Following your reasoning in part b, suggest why this mixture is produced (hint: consider steric effects and carbocation stability) (3 points) 6) Draw the products from the oxidation sequence shown below in the boxes: (6 points) 7) i) The tertiary alcohol shown can be prepared in 3 steps using carbonyl addition and alcohol oxidation chemistry. Identify the starting material X and suggest a plausible order for the three steps . To help you, some relevant reagents and starting materials are shown underneath. (9 points) ii) A student correctly suggests that the synthesis could be performed in one step using 2butanone as the starting material. How could this be done? (3 points) 8) i) Suggest an alkyl halide and a carbonyl starting material for preparation of the alkene below using a Wittig reaction (in addition to triphenylphosphine, illustrated) (6 points): ii) Show how you would prepare the phosphorus ylide necessary for the reaction (4 points): 9) Fill in reagents for the following transformations (2 points each):