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25.5: Isomers

Last updated

Mar 21, 2025
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- 25.4: Alkenes and Alkynes
- 25.6: Cyclic Hydrocarbons

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As we delve into the complexities of organic chemistry, we will see how molecular shape affects reactions. One common reaction for alkenes is the addition of hydrogen across the double bond to form the corresponding alkane. Because of the geometry of the reaction, the different 2-butene shapes have different heats of reaction. These differences are important, both from a theoretical standpoint, as well as from the point of view of industrial applications. Greater energy requirements mean a higher cost and a more expensive product.

Isomers

One of the interesting aspects of organic chemistry is that it is three-dimensional. A molecule can have a shape in space that may contribute to its properties. Molecules can differ in the way the atoms are arranged—the same combination of atoms can be assembled in more than one way. These compounds are known as isomers. Isomers are molecules with the same molecular formulas, but different arrangements of atoms. We will look at some isomer possibilities for alkanes and alkenes.

Structural Isomers

A structural isomer is one in which two or more organic compounds have the same molecular formulas, but different structures. The two pentane molecules below differ only in the location of the methyl group.

Structural formulas of 2-methylpentane and 3-methylpentane, showing linear carbon chains with a CH₃ group attached to the second and third carbon, respectively.

Alkenes can also demonstrate structural isomerism. In alkenes, there are multiple structural isomers based on where in the chain the double bond occurs. The condensed structural formulas of 1-butene and 2-butene show this.

Two chemical structures are shown: 1-butene with the double bond between the first and second carbons, and 2-butene with the double bond between the second and third carbons.

The number in the name of the alkene refers to the lowest numbered carbon in the chain that is part of the double bond.

Geometric Isomers

With a molecule such as 2-butene, a different type of isomerism called geometric isomerism can be observed. Geometric isomers are isomers in which the order of atom bonding is the same, but the arrangement of atoms in space is different. The double bond in an alkene is not free to rotate because of the nature of the pi bond. Therefore, there are two different ways to construct the 2-butene molecule. The image below shows the two geometric isomers, called cis-2-butene and trans-2-butene.

Diagram of cis-2-butene and trans-2-butene. Each includes a structural formula and a 3D ball-and-stick model, showcasing the different spatial arrangements of the molecules.

The cis isomer has the two single hydrogen atoms on the same side of the molecule, while the trans isomer has them on opposite sides of the molecule. In both molecules, the bonding order of the atoms is the same. In order for geometric isomers to exist, there must be a rigid structure in the molecule to prevent free rotation around a bond. If the double bond in an alkene was capable of rotating, the two geometric isomers above would not exist. In addition, the two carbon atoms must each have two different groups attached in order for there to be geometric isomers. Propene has no geometric isomers because one of the carbon atoms has two single hydrogens bonded to it.

Structural formula of ethene (ethylene), showing a double bond between two carbon atoms, with each carbon also bonded to two hydrogen atoms.

Physical and chemical properties of geometric isomers are generally different. While cis-2-butene is a polar molecule, trans-2-butene is nonpolar. Heat or irradiation with light can be used to bring about the conversion of one geometric isomer to another. The input of energy must be large enough to break the pi bond between the two carbon atoms, which is weaker than the sigma bond. At that point, the now single bond is free to rotate, and the isomers can interconvert.

As with alkenes, alkynes display structural isomerism beginning with 1-butyne and 2-butyne. However, there are no geometric isomers with alkynes, because there is only one other group bonded to the carbon atoms that are involved in the triple bond.

Summary

Isomers are molecules with the same molecular formulas, but different arrangements of atoms.
A structural isomer is one in which two or more organic compounds have the same molecular formulas, but different structures.
Geometric isomers are isomers in which the order of atom bonding is the same, but the arrangement of atoms in space is different.
Examples of alkane and alkene isomers are given.

Isomers

Structural Isomers

Geometric Isomers

Summary

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