Question

Methyl ethanoate has many more atoms than its parent acid, ethanoic acid. Yet methyl ethanoate (BP \(59^{\circ} \mathrm{C}\) ) boils at a much lower temperature than ethanoic acid (BP \(118^{\circ} \mathrm{C}\) ). How can this be explained?

Short answer

Ethanoic acid has a higher boiling point than methyl ethanoate because it can form stronger intermolecular hydrogen bonds, requiring more energy to overcome these forces during the phase change from liquid to gas.

Step-by-step solution

- Analyze Chemical Structures

Understand and compare the chemical structures of methyl ethanoate and ethanoic acid. Methyl ethanoate, also known as methyl acetate, has the formula CH3COOCH3, while ethanoic acid, also known as acetic acid, has the formula CH3COOH. Despite having more atoms, methyl ethanoate lacks the ability to form hydrogen bonds as strongly as ethanoic acid.

- Understand Intermolecular Forces

Intermolecular forces dictate the boiling points of substances. Stronger intermolecular forces result in higher boiling points. Ethanoic acid can form strong hydrogen bonds due to the hydroxyl group (OH), while methyl ethanoate can only engage in weaker dipole-dipole interactions and Van der Waals forces.

- Explain the Boiling Point Difference

Since ethanoic acid can form strong intermolecular hydrogen bonds, its molecules require more energy to separate, leading to a higher boiling point. Methyl ethanoate, while having more atoms, cannot form such strong intermolecular hydrogen bonds, therefore, it boils at a significantly lower temperature.

Key concepts

Hydrogen Bonding

Understanding hydrogen bonding is essential when exploring boiling points in chemistry. Hydrogen bonds are a type of strong dipole-dipole interaction that can occur when hydrogen is covalently bonded to a highly electronegative atom, such as oxygen or nitrogen.

These bonds are particularly relevant in substances like ethanoic acid (acetic acid), which contains a hydroxyl group allowing for the formation of hydrogen bonds. These interactions are significantly stronger than other types of intermolecular forces, requiring more thermal energy to break. As a result, substances capable of forming hydrogen bonds often have higher boiling points.

In the context of our problem, ethanoic acid forms hydrogen bonds between its molecules, which explains its comparatively high boiling point of \(118^{\text{\circ}} \text{C}\) .

Chemical Structure Analysis

The process of chemical structure analysis involves examining the molecular composition and arrangement of atoms within a compound. This approach is crucial when assessing how different molecules interact with each other, leading to varied physical properties.

In the given exercise, analyzing the chemical structures of methyl ethanoate and ethanoic acid reveals why their boiling points differ. Despite having a greater number of atoms, methyl ethanoate lacks the appropriate structure to form hydrogen bonds like ethanoic acid, which possesses a hydroxyl group enabling this stronger attraction. Therefore, its structure contributes to a lower boiling point.

A detailed structural analysis provides insight into the presence or absence of functional groups capable of stronger intermolecular interactions, explaining the observed variation in boiling points.

Intermolecular Forces

Intermolecular forces are attractions that mediate the interactions between molecules in a substance. They are responsible for properties like boiling and melting points, solubility, and viscosity.

The primary types of intermolecular forces include hydrogen bonding, dipole-dipole interactions, and Van der Waals forces, which encompass London dispersion forces. In our example, we see that although methyl ethanoate has a more complex structure with more atoms, it is the strength of the intermolecular forces, not the size, that dictates the boiling point.

Ethanoic acid, with its ability to form strong hydrogen bonds, exhibits higher boiling points than methyl ethanoate, which is restricted to weaker intermolecular forces due to its chemical structure.

Dipole-Dipole Interactions

Dipole-dipole interactions occur between polar molecules, where the positive end of one molecule attracts the negative end of another. They are weaker than hydrogen bonds but stronger than Van der Waals forces.

Methyl ethanoate, although unable to form hydrogen bonds, exhibits dipole-dipole interactions as it is a polar molecule. These interactions nonetheless contribute to its overall boiling point. The relatively moderate strength of dipole-dipole forces in methyl ethanoate leads to a lower boiling point compared to ethanoic acid's hydrogen bonds but still impacts how the molecules cohere at different temperatures.

Van der Waals Forces

Van der Waals forces are the weakest type of intermolecular forces and include attractions and repulsions between atoms, molecules, and surfaces, as well as other types of intermolecular interaction like London dispersion forces.

These forces arise from the transient polarization of electrons in atoms and molecules, inducing temporary dipoles. Methyl ethanoate's boiling point is affected by these forces, but to a lesser degree than by hydrogen bonding or permanent dipole-dipole interactions. Since all molecules exhibit Van der Waals forces, they always play a role in the determination of boiling points, but are usually only dominant in non-polar molecules or those without the capacity for stronger interactions.