Skip to ContentGo to accessibility pageKeyboard shortcuts menu
OpenStax Logo

4 • Summary

4 • Summary

Cyclic molecules are so commonly encountered throughout organic and biological chemistry that it’s important to understand the consequences of their cyclic structures. Thus, we’ve taken a close look at cyclic structures in this chapter.

Cycloalkanes are saturated cyclic hydrocarbons with the general formula CnH2n. In contrast to open-chain alkanes, where nearly free rotation occurs around C−C bonds, rotation is greatly reduced in cycloalkanes. Disubstituted cycloalkanes can therefore exist as cis–trans isomers. The cis isomer has both substituents on the same side of the ring; the trans isomer has substituents on opposite sides. Cis–trans isomers are just one kind of stereoisomer—compounds that have the same connections between atoms but different three-dimensional arrangements.

Not all cycloalkanes are equally stable. Three kinds of strain contribute to the overall energy of a cycloalkane: (1) angle strain is the resistance of a bond angle to compression or expansion from the normal 109° tetrahedral value, (2) torsional strain is the energy cost of having neighboring C−H bonds eclipsed rather than staggered, and (3) steric strain is the repulsive interaction that arises when two groups attempt to occupy the same space.

Cyclopropane (115 kJ/mol strain) and cyclobutane (110.4 kJ/mol strain) have both angle strain and torsional strain. Cyclopentane is free of angle strain but has a substantial torsional strain due to its large number of eclipsing interactions. Both cyclobutane and cyclopentane pucker slightly away from planarity to relieve torsional strain.

Cyclohexane is strain-free because it adopts a puckered chair conformation, in which all bond angles are near 109° and all neighboring C–H bonds are staggered. Chair cyclohexane has two kinds of positions: axial and equatorial. Axial positions are oriented up and down, parallel to the ring axis, while equatorial positions lie in a belt around the equator of the ring. Each carbon atom has one axial and one equatorial position.

Chair cyclohexanes are conformationally mobile and can undergo a ring-flip, which interconverts axial and equatorial positions. Substituents on the ring are more stable in the equatorial position because axial substituents cause 1,3-diaxial interactions. The amount of 1,3-diaxial steric strain caused by an axial substituent depends on its size.

Citation/Attribution

This book may not be used in the training of large language models or otherwise be ingested into large language models or generative AI offerings without OpenStax's permission.

Want to cite, share, or modify this book? This book uses the Creative Commons Attribution-NonCommercial-ShareAlike License and you must attribute OpenStax.

Attribution information
  • If you are redistributing all or part of this book in a print format, then you must include on every physical page the following attribution:
    Access for free at https://openstax.org/books/organic-chemistry/pages/1-why-this-chapter
  • If you are redistributing all or part of this book in a digital format, then you must include on every digital page view the following attribution:
    Access for free at https://openstax.org/books/organic-chemistry/pages/1-why-this-chapter
Citation information

© Aug 5, 2024 OpenStax. Textbook content produced by OpenStax is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike License . The OpenStax name, OpenStax logo, OpenStax book covers, OpenStax CNX name, and OpenStax CNX logo are not subject to the Creative Commons license and may not be reproduced without the prior and express written consent of Rice University.