CHM249 2005Test 2 - the pathway to the product. Cl NaNH 2 /...

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Name: 1 CHEMISTRY 249S Examination 2 March 24th 2005 Answer all questions in the spaces provided on the examination sheets, indicating clearly what is to be graded. PRINT YOUR NAME AND STUDENT NUMBER CLEARLY ON THE FIRST PAGE OF THE EXAM BOOKLET NAME: STUDENT NUMBER: Allowed Aids: Molecular Models Calculators and other electronic devices are not permitted in this examination Credit will be given for partial answers WAIT UNTIL YOU ARE TOLD TO BEGIN Marking Scheme Question 1 50 Question 2 25 Question 3 35 Question 4 40 Good Luck! Total 150
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Name: 2 1. Draw the final product of the following reactions. You may assume standard aqueous work- up are used as required. ( 50 Points ) (a) NaBH 4 O H (b) O MeOH / H + (c) Cl NO 2 NO 2 NaOH / H 2 O / (d) (i) AlCl 3 / O Cl (1 equiv) (e) O OCH 3 H 2 / Pd (f) Cl (i) Br 2 / / (PhCOO) 2 (ii) PhS
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Name: 3 (g) Ph 3 P Br (i) BuLi (ii) O H 2. ( 25 Points ) Draw a mechanism for the following transformation. Your answer should clearly indicate electron pair-movement using “arrow-pushing” and show all intermediates on
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Unformatted text preview: the pathway to the product. Cl NaNH 2 / NH 3 (liquid) NH 2 Name: 4 3. Suggest appropriate reagents to accomplish the following transformations. It is not necessary to draw mechanisms for your transformations. The stereochemistry of the final three compounds shown in the reaction scheme is not specified. Draw the stereochemistry of the final product, given the stereochemistry of compound A . ( 35 Points ) OH O Si O Si O Si OH OH O Si O O OH O O O O O TARGET MOLECULE H "A" Name: 5 4. Suggest concise syntheses of the following products using the starting materials indicated. In each case draw the reagents that you would use and the products obtained after each synthetic step. No more than four reactions are required for each synthesis. It is NOT necessary to write mechanisms for the reactions. ( 40 Points ) (a) COOH NH 2 Br CH 3 (b) O H O OH...
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CHM249 2005Test 2 - the pathway to the product. Cl NaNH 2 /...

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