Fall2008Blank - I . ( 25 points) Ph HO O H H HO OH H H Ph 4...

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Name _______________________ Page 1 F.08.215e3p1 I . (25 points) (a) Complete the following reaction sequence as required ( OL , 2007 9 , 311). H OH H HO OH H H O HO H O H O O H H O O Ph Ph Ph Ph H OH H O O H H O O Ph Ph Ph (b) The next step in the sequence is shown below. Provide a complete, step-wise mechanism for this reaction. H OH H O O H H O O Ph Ph Ph H H O O H H O O Ph Ph Ph OCH 3 H 3 CO OCH 3 OCH 3 H 3 CO OCH 3 DBSA, H 2 O DBSA is an acid catalyst; you may abbreviate it as HB, and its conjugate base as B H OH H O O H H O O Ph Ph Ph H H O O H H O O Ph Ph Ph OCH 3 H 3 CO OCH 3 17 4 4 also has the other anomer also has the other epimer
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Name _______________________ Page 2 F.08.215e3p2 I I . (30 points) (a) One of the molecules from Exam #2 (shown here) is an unnatural amino acid. It has two easily titrated protons (pK a 1 = 2.02 and pK a 2 = 5.98). Sketch out the titration curve, starting at low pH and proceeding through the addition of two equivalents of base. LABEL the following: (i) show location of pK a
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