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exam2key - orgo - CHEMISTRY 221 ORGANIC EXAM II KEY_D_1...

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CHEMISTRY 221 - ORGANIC EXAM II KEY _ D _1. Arrange the following bicyclic alkenes in order of increasing stability (least stable to most stable). a. III < II < I b. I < II < III c. I < III < II d. II < III < I _ B _2. The regiochemistry of hydroboration/oxidation of alkenes is: a. Markovnikov. b. anti-Markovnikov c. subject to solvent effects. d. unrelated to alkene structure. __ A _3. What alkene could you use to prepare the alkyl halide (1-chloroethyl)cyclohexane? i ii a. i only b. ii only c. both i and ii d. neither i or ii __ A _4. Rank the following sets of substituents in order of Cahn-Ingold-Prelog priorities (lowest priority highest) C N C CH CH 2 OCH 3 i ii iii a. i < ii < iii b. ii < iii < i c. iii < ii < i d. ii < i < iii __ D _5. The compound below has been isolated from the safflower plant. What is the degree of unsaturation for this compound? a. 6 b. 7 c. 8 d. 9 e. 10 C C C C C C C C C H H C C H H H C H 3 C H H I II III Cl (1-chloroethyl)cyclohexane
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6. Assign E or Z configuration to each of the double bonds in the compounds below. (2 each) Br OH OH O 1 1 1 1 Z Z 7. Circle:
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