problem set 5 Chem 3570.11.ps5 - 3. The compound...

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Chemistry 3570 Organic Chemistry for the Life Sciences PROBLEM SET 5 1. Please answer textbook questions 5.31, 5.32, 5.33, 5.35, 5.37(a)-(c), 5.48 (a), (b), (d)-(f) NOTE: The next two questions are more difficult than the typical 'problem set' questions. They require that you use your knowledge of the basic concepts of structure, bonding, and isomerism to "see" something new. Try your best at them before you consult the answer key. And don't fret over these problems -- the idea is to test whether you are honing the new learning skills, including reasoning by analogy, that were discussed in the first class. 2. When 3-deuterio-1-methyl-1-cyclohexene undergoes hydroboration-oxidation (i.e., using borane in diethyl ether followed by alkaline hydrogen peroxide), two different isotopically labelled alcohols are formed. Draw the structures of the two products.
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Unformatted text preview: 3. The compound azidobenzene has the formula C 6 H 5 N 3 , in which the azide functional group (N 3 ) is directly attached to a phenyl group. Azidobenzene reacts with ethylene as shown below, forming a new "heterocyclic" ring. [i.e. a ring with elements other than carbon.] Using the curved arrow formalism, suggest a mechanism for forming the new ring. Hint: It helps tremendously to draw a complete Lewis structure for azidobenzene, showing all formal charges. This reaction forms the basis of click chemistry, a term very recently coined by Nobel Laureate K. Barry Sharpless, and which is making a major impact on drug discovery in the pharmaceutical industry. You can check it out by Googling click chemistry. C 6 H 5 N 3 + H 2 C CH 2 N N N H H H H C 6 H 5...
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This note was uploaded on 03/13/2012 for the course CHEM 2183 at Cornell University (Engineering School).

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