Cycloalkanes are very important in components of food, pharmaceutical drugs, and much more. However, to use cycloalkanes in such applications, we must know the effects, functions, properties, and structures of cycloalkanes. Cycloalkanes are alkanes that are in the form of a ring; hence, the prefix cyclo-. Stable cycloalkanes cannot be formed with carbon chains of just any length. Recall that in alkanes, carbon adopts the sp3 tetrahedral geometry in which the angles between bonds are 109.5°. For some cycloalkanes to form, the angle between bonds must deviate from this ideal angle, an effect known as angle strain. Additionally, some hydrogen atoms may come into closer proximity with each other than is desirable (become eclipsed), an effect called torsional strain. These destabilizing effects, angle strain and torsional strain are known together as ring strain. The smaller cycloalkanes, cyclopropane and cyclobutane, have particularly high ring strains because their bond angles deviate substantially from 109.5° and their hydrogens eclipse each other. Cyclopentane is a more stable molecule with a small amount of ring strain, while cyclohexane is able to adopt the perfect geometry of a cycloalkane in which all angles are the ideal 109.5° and no hydrogens are eclipsed; it has no ring strain at all. Cycloalkanes larger than cyclohexane have ring strain and are not commonly encountered in organic lutz-heilmann.infoistry.

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Ring Strain and the Structures of Cycloalkanes

There are many forms of cycloalkanes, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, among others. The process of naming cycloalkanes is the same as naming alkanes but the addition of the prefix cyclo- is required. Cyclobutane is in a form of a square, which is highly unfavorable and unstable (this will be explained soon). There are different drawings for cyclobutane, but they are equivalent to each other. Cyclobutane can reduce the ring string by puckering the square cyclobutane. Cyclopentane takes the shape of a pentagon and cyclohexane is in the shape of a hexagon.


Some Conformations of Cyclohexane Rings. Image used with permission (William Reusch, MSU)

Although there are multiple ways to draw cyclohexane, the most stable and major conformer is the chair because is has a lower activation barrier from the energy diagram.


Conformational Energy Profile of Cyclohexane. Image used with permission (William Reusch, MSU).

The transition state structure is called a half chair. This energy diagram shows that the chair conformation is lower in energy; therefore, it is more stable. The chair conformation is more stable because it does not have any steric hindrance or steric repulsion between the hydrogen bonds. By drawing cyclohexane in a chair conformation, we can see how the H"s are positioned. There are two positions for the H"s in the chair conformation, which are in an axial or an equitorial formation.


This is how a chair conformation looks, but you"re probably wondering which H"s are in the equitorial and axial form. Here are more pictures to help.


These are hydrogens in the axial form.


These hydrogens are in an equitorial form. Of these two positions of the H"s, the equitorial form will be the most stable because the hydrogen atoms, or perhaps the other substituents, will not be touching each other. This is the best time to build a chair conformation in an equitorial and an axial form to demonstrate the stability of the equitorial form.


Most of the time, cyclohexane adopts the fully staggered, ideal angle chair conformation. In the chair conformation, if any carbon-carbon bond were examined, it would be found to exist with its substituents in the staggered conformation and all bonds would be found to possess an angle of 109.5°.


Cyclohexane in the chair conformation. Image used with permission (William Reusch, MSU).

In the chair conformation, hydrogen atoms are labeled according to their location. Those hydrogens which exist above or below the plane of the molecule (shown with red bonds above) are called axial. Those hydrogens which exist in the plane of the molecule (shown with blue bonds above) are called equatorial.

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Although the chair conformation is the most stable conformation that cyclohexane can adopt, there is enough thermal energy for it to also pass through less favorable conformations before returning to a different chair conformation. When it does so, the axial and equatorial substituents change places. The passage of cyclohexane from one chair conformation to another, during which the axial substituents switch places with the equatorial substituents, is called a ring flip.