practice-3-key - (Note: the molecule is shown in two...

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Practice Exam 3 (9/14/10) 1. Using systematic nomenclature, assign a name for the following compound. Br 2. Given the following compound name, draw a valid structure. 5-chloro-4-cyclopentyl-6-hepten-3-ol 1-bromo-8,8-dimethylbicyclo[3.2.1]octane Cl OH 3. Draw the two possible chair conformations with appropriate groups in equatorial or axial positions. Predict the most stable conformer and explain brieFy your reasoning. More stable The more stable one has two eqatorial methyls and one axial where as the less stable one has two axial and one equatorial methyls. The less stable one has more severe 1,3-diaxial interactions than the stable conformer. 4. Give the systematic name for the following compound. (No stereochemistry, please!) HO Br Cl 2,5-Dibromo-3-(1-chloroethyl)-6-ethyl-3-cyclohexen-1-ol Br
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5. Draw the following substituted cyclohexane as chair structures. Show both conformations (ring flip) and predict which will be more stable. (15 pts)
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Unformatted text preview: (Note: the molecule is shown in two different ways. They are the same compound) Me H H H Me Circle here if this is more stable. Circle here if this is more stable. Me Me 6. Give the structure of the following compound B first. Then give the structure and name of the reaction product. (15 pts) B 5-phenyl-2-cyclohexenol H 2 , Pd EtOH Product name OH Ph OH Ph 3-phenylcyclohexanol Cl H H 7. Draw the most stable conformation of 1-bromo-2-chloroethane using a Newman projection. Label anti, gauche or eclipsed for the form of your choice. (15 pts) The most stable conformation Label Br H H anti Cl HO Cl 8. Give the systematic names for the structures, and the structures for names. Answer all four questions. (20 pts) trans-5-sec-butyl-4-cyclopentyl-7-nonen-3-ol 1-chloro-8-ethyl-8-methylbicyclo [3.2.1]oct-2-ene 7-Chloro-4-isopropyl-2-methyl-1-hepten-5-yne 3-(1-Chloroethyl)-5-cyclopropyl-3-cyclohexen-1-ol OH Cl Cl =...
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This note was uploaded on 10/18/2010 for the course CHEM 322 A taught by Professor Bertolini during the Spring '10 term at USC.

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practice-3-key - (Note: the molecule is shown in two...

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