challenge_solutions_problem_set_3 - 28+x kJ/mol...

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Chem 359 Challenge Solutions Problem Set 3 Chapter 3: Organic Chemistry: A Biological Approach Key Ideas: 1. Functional Groups 2. Isomers 3. Conformers Challenge Problems: 1. No question. 2. Draw the following molecule in a skeletal structure and sawhorse representation. Draw the most stable conformer for all possible Newman projections. Plot potential energy vs. bond rotation diagram for one of these projections including approximate energies of intermediates. 2,3,3-trimethylpentane 1 2 3 4 5 3' 3' 1' H H H H H H H H H H H H H H H H H H H Me t-amyl H H H 1,2 2,3 H H Me Me Me i-Pr 3,4 H H H H H R 4,5 Me i-Pr Et H H H 3',3 H Me t-amyl H H H 1',2 Me Me Et Me Me H Energy Diagram for C2 to C3. Me Me Et Me Me H Me Me Et Me Me H Me Me Et Me Me H Me Me Et Me Me H Me Me Et Me Me H 0 o 60 o 120 o 180 o 240 o Me Me Et Me Me H 300 o Me Me Et Me Me H 360 o 11+11+(6+x)=
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Unformatted text preview: 28+x kJ/mol 3.8+3.8+3.8+(3.8+y)= 15.2+y kJ/mol 28 16 28+z kJ/mol 28+z kJ/mol 28+x kJ/mol 15.2+y kJ/mol 15.2+2y kJ/mol Energy kJ/mol x = Eclipsed interaction between H <-> Et y = Gauche interaction between CH 3 <-> Et z = Eclipsed interaction between Et <-> Me 3. Name the following compounds using IUPAC rules. 5-ethyl-2,2-dimethylheptane 5-cyclobutyl-1-cyclopropyl-3-ethyl-2-methylcyclohexane 8-sec-butyl-9-tert-butyl-7-isopentyl-6-isopropyl-12-neopentyloctadecane 3-ethyl-2,2,4,5,5-pentamethylhexane 1-sec-butyl-4-(2-methylbutyl)cycloheptane Note: You dont need to memorize octadecane...
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challenge_solutions_problem_set_3 - 28+x kJ/mol...

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