By Frederick A Bettelheim; et al
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Com/chemistry/ bettelheim to explore an interactive version of this figure. 6 What Are the Shapes of Alkanes and Cycloalkanes? ■ 29 B. Cycloalkanes We limit our discussion to the conformations of cyclopentanes and cyclohexanes because they are the carbon rings most commonly found in nature. Nonplanar or puckered conformations are favored in all cycloalkanes larger than cyclopropane. 6. In it, four carbon atoms are in a plane, and the fifth carbon atom is bent out of the plane, like an envelope with its flap bent upward.
Finally, draw line-angle formulas for all constitutional isomers with four carbons in a chain and two carbons as branches. Solution Here are line-angle formulas for all constitutional isomers with six, five, and four carbons in the longest chain. No constitutional isomers for C 6H 14 having only three carbons in the longest chain are possible. 3 Draw structural formulas for the three constitutional isomers with the molecular formula C 5H 12. Molecular Formula CH 4 C 5H 12 C 10H 22 C 15H 32 C 25H 52 C 30H 62 Number of Constitutional Isomers 1 3 75 4347 36,797,588 4,111,846,763 The ability of carbon atoms to form strong, stable bonds with other carbon atoms results in a staggering number of constitutional isomers, as the following table shows: Thus, for even a small number of carbon and hydrogen atoms, a very large number of constitutional isomers is possible.
Solution (a) Methylcyclopentane does not show cis-trans isomerism; it has only one substituent on the ring. (b) 1,1-Dimethylcyclobutane does not show cis-trans isomerism because only one arrangement is possible for the two methyl groups. Because both methyl groups are bonded to the same carbon, they must be trans to each other—one above the ring, the other below it. (c) 1,3-Dimethylcyclobutane shows cis-trans isomerism. The two methyl groups may be cis or they may be trans. 7 Which of the following cycloalkanes show cis-trans isomerism?