IC10 - 2.24.09

IC10 - 2.24.09 - A from the bromide starting material shown...

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Name : 1. Predict the product and draw a mechanism for the following reactions. a) O HO OH TsOH PhH Ę b) BrMg OMe OMe O THF C HEM 112B S CHOLARS I N -C LASS P ROBLEMS 10 2/24/09
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2. The following compound is an intermediate in a synthesis of streptenol A, a natural product. a) Identify the functional groups present in the compound. O O N N O b) Draw the mechanism for the reaction to form the intermediate. O O N N O O O NH 2 N O O PhH Ę
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c) A related substrate can be used to remove the ketone functionality. Draw the mechanism for the deoxygenation step ( B b C ). O O N H 2 N O O O Ę H 2 NNH 2 , KOH O O B C 3. Propose a synthesis of compound
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Unformatted text preview: A from the bromide starting material shown below. O O Br A 4. Compounds that contain both carbonyl and alcohol functional groups are often more stable as cyclic hemiacetals or cyclic acetals than as open-chain compounds. Examples of several of these are shown. Deduce the structure of the open-chain form of each. a) b) c) d) Brevicomin (sex attractant of Talaromycin A (a toxic substance produced Western pine beetle) by fungus that grows in poultry house litter)...
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IC10 - 2.24.09 - A from the bromide starting material shown...

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