By Melvin S. Newman
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Extra info for Organic Syntheses: v. 40
0]octane are isomers, and their heats of combustion can be compared on the basis of their relative stabilities. 0]octane. 0]nonane, has a greater number of carbons than either of the others and has the largest heat of combustion. 28 (a) The structural formula of 2,2,5,5-tetramethylhexane is (CH3)3CCH2CH2C(CH3)3. The substituents at C-3 are two hydrogens and a tert-butyl group. The substituents at C-4 are the same as those at C-3. The most stable conformation has the large tert-butyl groups anti to each other.
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-butyl3-methylcyclohexane the C-3 methyl group is equatorial. H H C(CH3)3 H3C (c) In trans-1-tert-butyl-4-methylcyclohexane both the tert-butyl and the C-4 methyl group are equatorial. H C(CH3)3 H3C H (d) Again the tert-butyl group is equatorial; however, in cis-1-tert-butyl-4-methylcyclohexane the methyl group on C-4 is axial.
One substituent is up and the other is down in the most stable conformation of trans-1isopropyl-3-methylcyclohexane. Begin as in part (c) by placing an isopropyl group in an equatorial orientation on a chair conformation of cyclohexane. H 1 3 CH(CH3)2 To be trans to the C-1 isopropyl group, the C-3 methyl group must be up. CH3 H CH(CH3)2 H (e) The bulkier isopropyl group is equatorial and the methyl group axial in the most stable conformation. To be cis to each other, one substituent must be axial and the other equatorial when they are located at positions 1 and 4 on a cyclohexane ring.