2002exam2sol - Massachusetts Institute of Technology...

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Unformatted text preview: Massachusetts Institute of Technology Organic Chemistry 5.13 Friday, March 22, 2002 Prof. Timothy F. Jamison Hour Exam #2 Name (please both print and sign your name) Recitation Instructor Directions: Closed book exam, no books, notebooks, notes, etc. allowed. However, calculators and molecular model sets are permitted. Please read through the entire exam before beginning, in order to make sure that you have all the pages and in order to gauge the relative difficulty of each question. Budget your time accordingly. Show all of your work if you wish to receive partial credit. You should have 9 pages total: 7 exam pages including this page and 2 blank pages for scratchwork. Question: ' Grader: 1. / 24 points 2. / 20 points 3. / 30 points 4 / 26 points Total: / 100 points 1. (24 points total) For all 8 reactions below, draw the structure of the predicted major product. Obey the Woodward-Hoffmann rules where applicable! Clearly indicate stereochemistry where relevant. For each pair of reactions, indicate which you would expect to be the faster one and the slower one by writing "faster" or "slower" in the boxes provided. a \ Br ' | g slower N/ faster or slower major product / \ 9&1”. IN! faster or slower major product Me Me Me b. 3m glbxwr‘ \A Eg‘ faster or slower major product I \ 41ml“ '" ”" faster or slower major Moduct Continued on next page 1. (Continued - see instructions on previous page) faster or slower ¢ (Li/571‘ is] “ major p oduct / 3(0Ww faster or slower ”96*” faster or slower @Mfi) pm ajor product 2. (20 points total) Like all cycloaddition reactions, the transformation below obeys the Woodward-Hoffmann rules. 0 C02Me heat I + I I ———-> O 002Me dimeth I . heptafulvene acetylenedicarboxylate crs product Circle the observed pro trans product a. (8 points) Classify the reaction above according to the Woodward- Hoffmann rules by filling in the 4 blanks below. [Eliot +n£3 b. (8 points) Circle the observed product above and briefly explain your choice in the space below. outwdlmod omé. MPJWQIVW c. (4 points) Is the product observed in the reaction above chiral or achiral? Explain briefly. Owl‘od (C2. Am; or; swmm> 3. (30 points) In the space provided, propose an efficient synthetic route to the target molecule shown in the box from cyclopentadiene and a dicarboxylic acid. Assume that your "stockroom" of available reagents includes any inorganic compounds. Your synthesis should provide a way to control the relative stereochemistry of the target molecule. Write your synthesis in the forward direction, showing all necessary reagents and relevant reaction conditions for each step. 4. (26 points total) a. (16 points) Draw the products of all reactions A-D shown below in the boxes provided. Clearly indicate relative stereochemistry, where applicable. (If the product of a given reaction is chiral, you need draw only one of the two possible enantiomers.) Me Me / hv heat % \ /‘l\ \ / Q. reaction A reaction B Me Me Oh; (Draw the product.) CCM (Draw the product.) / ——~ Me Me hv heat / Me ——> ——> \ reaction C reaction D Me d (D h d t) T rawt epro uc. (fa/i ,3 f” b. (10 points) in one of the 4 reactions above, 2 products that are not enantiomeric to one another are allowed by the Woodward-Hoffmann rules. Which reaction is it (La A, B, C, or D)? Draw the structure of the product not formed and briefly explain why it is not observed, even though the Woodward- Hoffmann rules do not exclude the possibility of its formation. H CD) M/ AM“ 5 ’av \/\\ 6% t’\ (9D V ...
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