koofer(8) - [c Draw the syndiotactic form for the structure...

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Week 2, problem set 1; Chem. 109C, summer 2006 The structure illustrated below is that of D-glucose. It is portrayed in its open form as the so-called zig-zag formulation. Zig-zag formulations are exceptionally common, and are used by all organic chemists. [a] Make a model of the structure. [b] Identify the asymmetric carbons … the so-called chiral centers. [c] Draw the enantiomer. [d] Draw a structure corresponding to a diastereomer at C-3. [e] Determine the absolute configuration at C-5. [f] Is the structure an example of an aldohexose or a ketohexose? How do you know? HO CHO OH OH OH OH 2 3 4 5 6 1 2. Identify the anomeric carbon in each structure, should one exist. O O HO OH OH OH OH OCH 3 O HO HO HO HO 3. [a] Identify the repeat unit in the following short chain polymer (a so-called oligomer). R R' OAc OAc OAc OAc OAc OAc OAc OAc OAc [b] What is the structure of the monomer that could be used to assemble this structure?
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Unformatted text preview: [c] Draw the syndiotactic form for the structure shown above. 4. [a] Formulate a mechanism to show how the structures shown below are interconverted. Hint: Use your knowledge concerning benzylic cations. [b] Why does the equilibrium lie to the right? catalytic H 5. Use Grignard chemistry to show how each of the structures shown below could be synthesized [a review from last Friday]. OH OH OH O 6. [Note: Each of the transformations shown below has its counterpart in carbohydrate chemistry. Be aware of this as you study carbohydrates.] Provide reagents that would allow each of the transformations shown below to take place efficiently. CHO OH CHO CO 2 H O OCH 3 O Ph note: CH 2 Ph = benzyl. sometimes abbreviated "Bn" O note: CH 3 O = acetyl, abbreviated "Ac"...
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