Portmess Homework Q&S 55

Portmess Homework Q&S 55 - d Again the tert-butyl...

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All methyl groups are equatorial in cis -1,3,5-trimethylcyclohexane. It is more stable than trans - 1,3,5-trimethylcyclohexane (shown in the following), which has one axial methyl group in its most stable conformation. 3.10 In each of these problems, a tert -butyl group is the larger substituent and will be equatorial in the most stable conformation. Draw a chair conformation of cyclohexane, add an equatorial tert -butyl group, and then add the remaining substituent so as to give the required cis or trans relationship to the tert -butyl group. ( b ) Begin by drawing a chair cyclohexane with an equatorial tert -butyl group. In cis -1- tert -butyl- 3-methylcyclohexane the C-3 methyl group is equatorial. ( c ) In trans -1- tert -butyl-4-methylcyclohexane both the tert -butyl and the C-4 methyl group are equatorial.
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Unformatted text preview: ( d ) Again the tert-butyl group is equatorial; however, in cis-1-tert-butyl-4-methylcyclohexane the methyl group on C-4 is axial. 3.11 Isomers are different compounds that have the same molecular formula. Compare the molecular formulas of the compounds given to the molecular formula of spiropentane. Only the two compounds that have the molecular formula C 5 H 8 are isomers of spiropentane. 3.12 Two bond cleavages convert bicyclobutane to a noncyclic species; therefore, bicyclobutane is bicyclic. Spiropentane (C 5 H 8 ) CH CH 2 C 5 H 8 C 6 H 10 C 5 H 8 C 5 H 10 CH 2 CH 3 H C(CH 3 ) 3 H H 3 C H C(CH 3 ) 3 H H H 3 C H C(CH 3 ) 3 H H H H 3 C CH 3 H 3 C trans-1,3,5-Trimethylcyclohexane CH 3 CH 3 H H CH 3 H CONFORMATIONS OF ALKANES AND CYCLOALKANES 49...
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