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Explain why methanethiol, \(\mathrm{CH}_{3} \mathrm{SH}\), has a lower boiling point \(\left(6^{\circ} \mathrm{C}\right)\) than methanol, \(\mathrm{CH}_{3} \mathrm{OH}\left(65^{\circ} \mathrm{C}\right)\), even though methanethiol has a higher molecular weight.

Short Answer

Expert verified
Methanol boils at a higher temperature because its molecules form strong hydrogen bonds, unlike methanethiol which has weaker interactions.

Step by step solution

01

Understanding Boiling Point

The boiling point of a substance is determined by the forces holding its molecules together in the liquid state. Higher boiling points indicate stronger intermolecular forces.
02

Intermolecular Forces in Methanol

Methanol (\(\mathrm{CH}_3\mathrm{OH}\)) has hydrogen bonds due to the presence of an \(-\mathrm{OH}\) group. These hydrogen bonds are strong intermolecular forces that result in a higher boiling point.
03

Intermolecular Forces in Methanethiol

Methanethiol (\(\mathrm{CH}_3\mathrm{SH}\)) has weaker dipole-dipole interactions and possibly London dispersion forces. The sulfur atom does not engage in hydrogen bonding strongly like the oxygen in methanol, resulting in a lower boiling point than methanol.
04

Comparing Molecular Weights

Although methanethiol has a higher molecular weight than methanol, molecular weight is less influential on boiling point than the type and strength of intermolecular forces present. Methanol's hydrogen bonding outweighs the effect of molecular weight difference.
05

Conclusion

Methanol has a higher boiling point than methanethiol primarily due to the presence of strong hydrogen bonds in methanol, which are absent in methanethiol. This demonstrates that the boiling point is more significantly affected by the strength of intermolecular forces rather than molecular weight.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Hydrogen Bonding
Hydrogen bonding is a type of strong intermolecular force that occurs when a hydrogen atom is covalently bonded to electronegative atoms like oxygen, nitrogen, or fluorine, creating a significant dipole. This dipole allows the hydrogen atom to interact with another electronegative atom in a neighboring molecule. It is essential in determining the physical properties, such as boiling points, of molecules.
For example, in methanol (\(\mathrm{CH}_3\mathrm{OH}\)), the oxygen atom in the hydroxyl group (\(-\mathrm{OH}\)) forms a hydrogen bond with the hydrogen of another methanol molecule.
  • This creates a stronger attraction between molecules.
  • Hydrogen bonding requires more energy to break compared to other intermolecular forces.
  • It notably elevates the boiling point, as additional heat must be provided to overcome these forces.
In contrast, methanethiol (\(\mathrm{CH}_3\mathrm{SH}\)) lacks this ability to form strong hydrogen bonds as sulfur is less electronegative than oxygen, which explains its significantly lower boiling point.
Boiling Point
The boiling point of a substance is a physical property that indicates the temperature at which the liquid form of that substance becomes a gas. The boiling point reflects how much energy is needed to overcome the intermolecular forces binding the molecules together in the liquid state.
Strong intermolecular forces result in a high boiling point because more energy is required to separate the molecules, while weak forces lead to a low boiling point.
  • The stronger the intermolecular forces, such as hydrogen bonds, the higher the boiling point.
  • Weaker forces, like dipole-dipole interactions or London dispersion forces, generally result in a lower boiling point.
This concept is exemplified by methanol and methanethiol, where methanol has a higher boiling point due to the presence of hydrogen bonds, unlike methanethiol.
Methanol
Methanol (\(\mathrm{CH}_3\mathrm{OH}\)) is a small organic molecule with the chemical structure consisting of one carbon, three hydrogen atoms, and a hydroxyl group (\(-\mathrm{OH}\)). The presence of the hydroxyl group provides methanol with the ability to form hydrogen bonds, resulting in several distinct characteristics:
  • Strong hydrogen bonding leads to a high boiling point of \(65^{\circ} \mathrm{C}\).
  • Hydrogen bonding is responsible for its higher solubility in water compared to compounds of similar molecular weight.
  • The strong intermolecular forces impact its physical properties and reactivity.
Methanol's structural ability to engage in hydrogen bonding manifests in physical behaviors, such as its boiling point and interactions with other polar molecules like water.
Methanethiol
Methanethiol (\(\mathrm{CH}_3\mathrm{SH}\)) is structurally similar to methanol but contains a thiol group (\(-\mathrm{SH}\)) instead of the hydroxyl group. This change greatly influences its intermolecular interactions and properties.
  • It has a boiling point of \(6^{\circ} \mathrm{C}\), considerably lower than methanol.
  • Methanethiol lacks strong hydrogen bonding because sulfur does not attract electrons as effectively as oxygen.
  • Instead, it primarily relies on weaker dipole-dipole interactions and London dispersion forces.
These weaker forces result in methanethiol requiring less energy to transition into the gaseous state, contributing to its lower boiling point compared to methanol.

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Most popular questions from this chapter

Write a balanced equation for the complete combustion of ethanol, the alcohol blended with gasoline to produce E85.

Considering the hydrogen bonding intermolecular force, explain why glycerol is much thicker (more viscous than ethylene glycol, which in turn is much more viscous than ethanol.

Following are structural formulas for 1 -butanol and 1-butanethiol. One of these compounds has a boiling point of \(98^{\circ} \mathrm{C}\) and the other has a boiling point of \(117^{\circ} \mathrm{C} .\) Which compound has which boiling point? \\[ \begin{array}{cc} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH} & \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{SH} \\\ 1-\text { Butanol } & 1 \text { -Butanethiol } \end{array} \\]

What is the difference in structure between a primary, a secondary, and a tertiary alcohol?

Answer true or false. (a) The two most important reactions of alcohols are their acid-catalyzed dehydration to give alkenes and their oxidation to aldehydes, ketones, and carboxylic acids. (b) The acidity of alcohols is comparable to that of water (c) Water-insoluble alcohols and water-insoluble phenols react with strong bases to give water-soluble salts. (d) Acid-catalyzed dehydration of cyclohexanol gives cyclohexane. (e) When the acid-catalyzed dehydration of an alcohol can yield isomeric alkenes, the alkene with the greater number of hydrogens on the carbons of the double bond generally predominates. (f) The acid-catalyzed dehydration of 2-butanol gives predominantly 1-butene. (g) The oxidation of a primary alcohol gives either an aldehyde or a carboxylic acid depending on experimental conditions. (h) The oxidation of a secondary alcohol gives a carboxylic acid. (i) Acetic acid, \(\mathrm{CH}_{3} \mathrm{COOH}\), can be prepared from ethylene, \(\mathrm{CH}_{2}=\mathrm{CH}_{2}\), by treatment of ethylene with \(\mathrm{H}_{2} \mathrm{O} / \mathrm{H}_{2} \mathrm{SO}_{4},\) followed by treatment with \(\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7} / \mathrm{H}_{2} \mathrm{SO}_{4}\) (j) Treatment of propene, \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2},\) with \(\mathrm{H}_{2} \mathrm{O} /\) \(\mathrm{H}_{2} \mathrm{SO}_{4}\) followed by treatment with \(\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7} / \mathrm{H}_{2} \mathrm{SO}_{4}\) gives propanoic acid, \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}\)

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