Problem_Set_6

Problem_Set_6 - HO HO HO O OH OH OH OH HO a. c. b. 3....

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Organic Chemistry c3046y Problem Set 6 - Carbohydrates Relevant Book Problems: 21.52, 21.55. Relevant Reading: 21.1-21.5, 21.8, 21.9, 21.11, 21.12, 21.13, 21.16, 21.17. CH 2 OH OH H OH H H HO H HO CH 2 OH H HO OH H H HO O CH 2 OH CH 2 OH OH H H HO H HO O H as a β -furanose 1. Provide a "normal" (chair or wedges and dashes) representation of the following carbohydrates in the indicated form: a. b. as a β -pyranose c. as an α -furanose H O Propose syntheses to achieve the following transformations: 2. a. from CH 2 OH OH H OH H b. CH 2 OH OH H H HO from CH 2 OH OH H H HO H HO CH 2 OH OH H OH H H HO H HO H O H O H O H O O OH HO OH OH OH O OH
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Unformatted text preview: HO HO HO O OH OH OH OH HO a. c. b. 3. Provide a classification ( e.g. D-aldopentose or L-ketohexose etc.) and the Fischer Projection representation for the following carbohydrates: page 2 5. Predict the product of the following sequence of reactions: 4. Provide a mechanism for the following transformation: C CH 2 OH OH H OH H H O CH 2 OH CH 2 OH O OH H OH, H 2 O O BnO BnO BnO Me Me O O O BnO OBn OBn HO 1. 2. ZnCl 2 , 3. H 2 , Pd...
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Problem_Set_6 - HO HO HO O OH OH OH OH HO a. c. b. 3....

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