Practice_Ex_2_08_32

Practice_Ex_2_08_32 - /H + Page 6 3. Show all steps in the...

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Page 1 PRACTICE EXAM TWO CHEMISTRY 0320 PROF. C. S. WILCOX SPRING 2008 NAME ___________________________________
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Page 2 1. Provide the MAJOR product or the necessary reagents for each of the following reactions. (48 points total) Cl O MgBr NH 2 O O O OH OH - 1) LiCu(CH 3 ) NH 2 O OH Br a b c d e f + HN(CH 3 ) 2 2) H 2 O O OH O 1) NaCN/H +
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Page 3 1. (Continued) NH OH O SOCl 2 C N Cl O N C O CH 3 C O CH 3
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Page 4 2. For each of the following transformations, provide mechanisms. i. Show each bond forming step, including deprotonations and protonations. ii. Show correct formal charges on each atom that is not neutral. iii. Curved arrow drawing (to show electron movement) will not affect grading. iv. You may use ‘’ H + ‘’ as the acid (proton) source only in acid catalyzed reactions. v. In base catalyzed reactions, show an appropriate source for protonation. (for example, H 2 O or HOR). a. NH 2 O H 2 O NH 2 Br 2 /NaOH b. O O OH - O (Robinson annulation) +
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Page 5 c. O Br 2 O Br bromination
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Unformatted text preview: /H + Page 6 3. Show all steps in the conversion of Acetyl CoA to isoprenylpyrophosphate. SCoA O H 3 C H 2 C C H 2 CH 3 H 2 C O-O P O-O O P O-O isoprenyl pyrophosphate how? Page 7 4. Provide a synthetic pathway for converting cyclohexanone into the bicyclic product shown below: O CH 3 CN O You may use cyclohexanone, inorganic reagents, and carbon containing reactants containing four carbons or less. Page 8 5. The following two molecules are diastereomers. They can be separated, but the action of any base causes them to interconvert. Explain this observation by providing a reasonable mechanism for the interconversion. N + CH 2 CH 3 H 3 C O A N + CH 3 H 3 CH 2 C O B Base 6. Show how you would prepare the lactone below from methyl vinyl ketone and inorganic reagents. O O O...
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Practice_Ex_2_08_32 - /H + Page 6 3. Show all steps in the...

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