261 f06 exam 2 soln key

261 f06 exam 2 soln key - Chem 261 F06 Dr. Mbadugha Name:...

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Chem 261 F06 Name: Soln Key Dr. Mbadugha Exam II, 10/24/06 1) 6 pt a. Circle the alcohol below that CAN be made selectively by hydroboration/oxidation of methylcyclohexene. HO H OH H HO H CH 3 H 3 C H 3 C OH H 3 C H 2 pt b. For each pair below, circle the alcohol that is more efficiently prepared by acid- catalyzed hydration of an alkene. 2-pentanol vs 3-pentanol 2 pt 2-methyl-2-pentanol vs 3,3-dimethyl-2-butanol 2 pt 2) 6 pt a. Place double bonds and methyl groups on the carbon skeleton below to represent (1Z, 4E)-3,6-dimethyl-1,4-cyclodecediene. 3 pt; example: b. Circle the more stable cycloalkene in the pair below: 3 pt 1 2 3 4 5 6 7 8 1 pt bonus – name the second cycloalkene shown above – bicyclo[4.2.0]-7-octene (or bicyclo[4.2.0]-oct-7-ene) 1
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3) 10 pt Provide an acceptable name for the following – 2 pt each; 1 pt off for wrong alphabetical order, wrong locant numbering order, using wrong name (ex vinyl instead of allyl) or leaving off E/Z I F OH I F Br Cl A B C D E OH Br OH (Z)-1-bromo-2-chloro-1-fluoro-2-iodoethene or (Z)-1-bromo-2-chloro-1-fluoro-2- iodoethylene 4-ethyl-3,3-dimethyl-1-cyclobutene or 4-ethyl-3,3-dimethylcyclobutene 2-fluoro-1-iodo-3-methyl-2-buten-1-ol or 2-fluoro-1-iodo-3-methyl-2-butenol (1E,3E)-2-ethyl-1,3,5-hexatrien-1-ol or (1E,3E)-2-ethyl-1,3,5-hexatrienol
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261 f06 exam 2 soln key - Chem 261 F06 Dr. Mbadugha Name:...

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