Question

3. (15 points) 1) Consider both reactions A and B below. Both reactions start from alkenes to generate the same alcohol. However, the mechanism is distinct for reaction A and reaction B. H/HO HO H*/H20 но 1) Propose a reasonable mechanism for reaction A, with curved arrows for each step. 2) Propose a reasonable mechanism for reaction B, with curved arrows for each step. Question 3 continues 3) In the space below, describe the rate determining step for both reaction A AND reaction B. Explain your answer in 2-3 sentences 4) Predict whether reaction A or reaction B will be faster, or if reaction A AND reaction B will proceed with a similar in rate. Give al sentence explanation for your answer. 5) Describe the stereochemical outcomes of products of both reactions A and B, explain in 1 sentence II) Finally consider the reactions on molecules X and Y below. conc. NOCH con NOCH Explain why, molecule X undergoes efficient climination (with some possible minor substitution products), while molecule Y under the same conditions only undergoes very slow substitution.

Answer 1

solution TH / Hoo HO H₂0 Go * Rate carlocation detem step (Most Stalte) (Direct SM breachion) product of A 1)B) 1,2-H Rate 30-carlocation 16 Shift determine Step go carlocation SN' with rearrangement * Rate determining Stepeis first step in both reaction KHO (when the formation 7 of carlocation thappen Product B iv) * first reaction in ist step -formation of ea 3o carlocation Most stable MB Reaction A will befaster. * und reaction in Ist steps formation of 2o convocation -- after hearrangement 30- cartoca non forned. due to this B reachon will be slower than A. (extra bond breaking & Bond forming happen in the Breaction