E4,241b,S06 - EXAM 3 CHEMISTRY 241b Dr Spurgeon ANSWER KEY...

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EXAM 3 CHEMISTRY 241b April 27, 2006 Dr. Spurgeon ANSWER KEY __________________________________________________________________________________________ 1. (19 points) Answer the following questions about sugars. a. (3pts. ea.) Provide either the Fischer projection or the name for each sugar: b. (10 pts) Convert the following cyclic forms to their representative open-chain Fischer projection and then name the open-chain form: D -Arabinose O H HO H HO OH OH H H H OH L -Gulose OH H H HO OH H H O H HO CH 2 OH O H HO OH H OH H H H H OH CHO H HO OH H OH H CH 2 OH α - D -Mannose CHO HO H HO H H OH HO H CH 2 OH CHO OH H OH H OH H OH H CH 2 OH D -Allose D -Arabinose CHO H HO OH H OH H CH 2 OH
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2. (23 points) Use the Kiliani-Fischer synthesis to show how Emil (this is what his friends called him!) prepared D -xylose and D -lyxose from their parent sugar. Fill-in the ‘cyclobutanes’ below with requisite starting material, reagent(s), and/or products; and fill-in the lines with the appropriate name. 3. (10 points) The last part of the Fischer proof was to take each sugar and oxidize it with __________. This resulted in the formation of an ______________ acid.
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