exam_4_xtra_prob - Massachusetts Institute of Technology...

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Massachusetts Institute of Technology 5.13, Fall 2006 EXAM 4 EXTRA PROBLEMS 1. Provide the best mechanism for the following reaction. Br _ OH/H 2 O O O_ Figure by MIT OCW. 2. A useful diketone, dimedone, can be prepared in high yield by the synthesis below. Provide structures for the intermediate A and for dimedone, and show a mechanism for each step up to B . O O EtO OEt O Me Me Me + NaOH EtOH NaOH EtOH A H 3 O + O Me Me H 2 O CO 2 Et NaOH O H 3 O + dimedone (B) Figure by MIT OCW. 3. A biochemist, Sal Monella, has come to you to ask your assistance in testing a promising biosynthetic hypothesis. She wishes to have two samples of methylsuccinic acid specifically labeled with 14 C as shown below. The source of the isotope, for financial reasons, is the salt Na 14 CN . Outline a synthesis that will accomplish this objective. CH 3 O CH 3 O (a) HO * OH (b) HO * OH O O Figure by MIT OCW.
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4. In early 1999, chemists from Tohoku Univerwsity in Japan reported that they had achieved the transformation shown below. In this equation, B: is a base strong enough to form enolate ions. Propose a reasonable mechanism for this transformation. (L 22.87) O CO 2 Me B: - O CO 2 Me Figure by MIT OCW. 5. With the aid of three-dimensional drawings, provide a clear rationale for the products that are observed in the following transformations. Your rationale must include the mechanism for each transformation. OTs
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

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exam_4_xtra_prob - Massachusetts Institute of Technology...

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