Problem_Set_6_Answer_Key

Problem_Set_6_Answer_Key - NaOAc MeOH CHO CH 2 OH H HO OH H...

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Organic Chemistry c3046y Problem Set 6 - Carbohydrates Answer Key O OH HO HO OH OH O HO OH HO HO O OH OH HO HO a. b. c. 1. Provide a "normal" (chair or wedges and dashes) representation of the following carbohydrates in the indicated form: OH Propose syntheses to achieve the following transformations: 2. a. CH 2 OH OH H OH H b. CH 2 OH OH H H HO 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 1. HCN 2. H 2 /Pd 3. H 3 O + CH 2 OH OH H OH H H HO O H 1. HCN 2. H 2 /Pd 3. H 3 O + This is just two rounds of the Killiani-Fischer Synthesis. Both times the HCN addition will give two products (diastereomers), and a separation of products will be required. H 2 NOH CH 2 OH OH H H HO H HO H N OH Me O O Me O CH 2 OH OH H H HO C H HO N NaOMe This is a Wohl Degradation.
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Unformatted text preview: NaOAc MeOH CHO CH 2 OH H HO OH H OH H HO H CH 2 OH CH 2 OH H HO OH H O CHO CH 2 OH OH H OH H H OH H HO L-aldohexose D-ketopentose D-aldohexose 3. a. b. c. page 2 5. Predict the product of the following sequence of reactions: 4. Provide a mechanism for the following transformation: O BnO BnO BnO Me Me O O O BnO OBn OBn HO 1. 2. ZnCl 2 , 3. H 2 , Pd O OH HO HO OH O O OH HO OH C CH 2 OH OH H OH H H O CH 2 OH CH 2 OH O OH H OH, H 2 O HO CH 2 OH OH OH H H O CH 2 OH O OH H H OH HO H CH 2 OH O OH H H OH H O H H O H...
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Problem_Set_6_Answer_Key - NaOAc MeOH CHO CH 2 OH H HO OH H...

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