634-F11_Midterm - Initials_ Chemistry 634, Fall 2011...

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Initials______________ Page 1/18 Chemistry 634, Fall 2011 Midterm Exam Prof. Donald Watson 300 points (2 hours) Closed note, closed book. No calculators allowed. You may use a molecular model set. Answers should be written in boxes provided . Other markings will not be considered. Scratch paper can be found at the back of the exam packet. Please initial each page at the top. Points will only be awarded for clearly communicated answers. Please make sure you have all pages of the exam packet (18 pages). Name _______________________________________ Question 1: ________/30 Question 2: ________/30 Question 3: ________/21 Question 4: ________/28 Question 5: ________/38 Question 6: ________/30 Question 7: ________/25 Question 8: ________/20 Question 9: ________/20 Question 10: _______/20 Question 11: _______/38 _____________________ Total:_______/300
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Initials______________ Page 2/18 1) (30 points, 6 points each) Predict the expected major product for each reaction sequence after aqueous work-up, drawing your answer in box provided. Denote stereochemistry where needed. If no reaction is expected, state so. _______/30 points OMe OMe C 5 H 11 BuLi, THF; then EtCHO N Ac NHBoc CO 2 Me I 10 mol% CuI 20 mol% 1 K 3 PO 4 , tol, 110 °C 1 N H H N Me Me Me OH O Me OTBDPS cat. Pr 4 N + RuO 4 - N O Me O N Me OMe BuMgCl F F H N CF 3 CO 2 H NHAc t BuCOCl, Et 3 N cat. DMAP
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Initials______________ Page 3/18 2) (30 points, 6 points each) Predict the expected major product for each reaction sequence after aqueous work-up, drawing your answer in box provided. Denote stereochemistry where needed. If no reaction is expected, state so.
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634-F11_Midterm - Initials_ Chemistry 634, Fall 2011...

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