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Question 1 20pts Five reactions are shown below. For each reaction, draw the products. Unless instructed otherwise, if multiple products can be formed, draw them all, and indicate which is major. Indicate stereochemical outcomes clearly. To do so, you may ed to draw more than one product or write explanatory words (e.g. "racemic"). e dashes and wedges only when you intend to indicate a particular stereochemistry. Upload all your answers to this question on a single page, labeled (a), b), c)..). and in order the questions are given below. NaOCH2CH3 just draw products; do not indicate major/minor a) CH3CH2OH QH SOCI2 b) pyridine QH NaNH2 c) OH H2SO4 heat d) CH3CH2OH draw only substitution products e) Question 2 14pts Two reactions are shown below. Drawa complete electron pushing mechanism for each reaction, and upload a single page containing both mechanisms. OH f) HBr Br + H2O (6 pt) racemic Br. OCH3 CH3OH + CH,OH2 o + (8 pt) Upload Choose File Question 3 12pts Two unrelated questions follow. Upload one page with the answer to h) Provide a synthesis of the product on the right from the starting material on the left. Your synthesis should take no more than three steps. (6 pt) al OH ??? i) One feature of the E2 reaction is that when very bulky bases are used, the less substituted alkene may be formed as the major reaction product. This is called non- Zaitsev regioselectivity. (6 pt) (CH3)3COK + Y major minor Sketch a reaction coordinate diagram that is consistent with this observation and the facts you know about E2 reactions. Assume both elimination processes are exothermic, and include all starting materials and products on your diagram. You do not need to sketch transition state structures, but do make sure their energies are accurately shown in your diagram.

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