Organic%20Chemistry%20I%20%20CHM2210%20Test%202

Organic%20Chemistry%20I%20%20CHM2210%20Test%202 - TEST 2...

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TEST 2 ( Version A) 1. Give the IUPAC names of the following compounds (20 pts). a) Cl 1-Chloro-2-methyl-4-propylcyclopentane b) 4,5-Diethyl-3,4-dimethyloctane c) Br Br CH 3 1,3-Dibromo-5-methylcyclohexane d) CH 3 CH 2 C(CH 3 ) 2 CH(CH 2 CH 3 )CH 2 CH 3 4-Ethyl-3,3-dimethyl-hexane e) Bicyclo[2.2.1]heptane 2. Draw structures corresponding to the following names (12 pts). a) 3-Ethyl-4,4-dimethylheptane
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b) 3-Isopropyl-2-methylhexane c) 8-Methylbicylo[4.3.0]nonane d) trans -1,3-Dimethylcyclobutane 3. Draw three of the constitutional isomers of C 6 H 14 , and give their IUPAC names (12 pts). hexane 2-methylpentane 3-methylpentane 2,2-dimethylbutane 2,3-dimethylbutane 4. (a) Considering 1-bromopropane, with sighting along the C2-C1 bond, draw Newman projections for the most stable and the least stable conformations. (5 pts) Most stable (staggered) Least stable (eclipsed) Br H H CH 3 H H H Br H CH 3 H H Methyl grp in front H 3 C
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(b) If the H-H eclipsing costs 4 kJ/mol and the halogen-methyl eclipsing interaction
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Organic%20Chemistry%20I%20%20CHM2210%20Test%202 - TEST 2...

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