The structural isomers of pentane, \(\mathrm{C}_{5} \mathrm{H}_{12}\), have quite different boiling points (see Example 11.1 ). Explain the observed variation in boiling point, in terms of structure.

Short Answer

Expert verified
The variation in boiling points of pentane isomers is due to their different structures, which affect the extent of intermolecular forces (London dispersion forces). Pentane, being a straight chain, has more surface area leading to stronger dispersion forces and a higher boiling point. Isopentane, with one branch, has less surface area and a slightly lower boiling point. Neopentane, almost spherical in structure due to multiple branches, has the least surface area and the lowest boiling point among the three.

Step by step solution

01

Understanding Isomers

First, understand the concept of isomers which are compounds with the same molecular formula, but different structural arrangement. Pentane \( \mathrm{C}_{5} \mathrm{H}_{12} \) has three structural isomers: pentane, isopentane (or 2-methylbutane), and neopentane (or 2,2-dimethylpropane). These different structures lead to different physical and chemical properties.
02

Examination of Molecular Structures

Examine the structures of the isomers. Pentane is a straight-chain compound, isopentane has a branch, while neopentane is almost spherical due to its branches. These varying structures lead to different amounts of surface area in contact between molecules, and thus, varying intermolecular forces.
03

Correlation between Intermolecular Forces and Boiling Points

Understand the impact of intermolecular forces on boiling points. Greater intermolecular forces require more energy (higher temperature) to break, hence, a higher boiling point. In these isomers, the intermolecular forces at play are the London dispersion forces (temporary induced dipole-induced dipole interactions). These forces are stronger in larger, more elongated molecules that have greater surface contact.
04

Applying the Knowledge to Pentane Isomers

Use the understanding gained in the previous steps to explain the boiling points of pentane isomers. Pentane, being a long chain, has more surface area and thus stronger London dispersion forces, leading to a higher boiling point. Isopentane, having one branch, has lesser surface area compared to pentane, hence, a slightly lower boiling point. Neopentane, being almost spherical due to many branches, has the least surface area leading to weakest dispersion forces and the lowest boiling point among the three.

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Key Concepts

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

Structural Isomers
When we talk about structural isomers, we refer to molecules that share the same molecular formula but differ dramatically in the way their atoms are connected. To visualize isomers, imagine several different ways to arrange a set of building blocks: while each structure is made from the same pieces, the final shapes can be quite distinct. This is exactly what happens with isomers like those of pentane (abla_{5}abla_{12}). In the case of pentane, we encounter three primary structural isomers: straight-chain pentane, branched-chain isopentane, and the more compact neopentane. Each isomer's unique arrangement leads to characteristic differences in physical and chemical properties, such as boiling points. These differences are critical to understand, especially when considering the application of these compounds in industry and research.

Lets take an example like pentane, it is a straight, unbranched chain, which can be likened to a line of building blocks. On the other hand, isomers like isopentane and neopentane are branched, leading to varied shapes akin to a tree with different patterns of branches.
Intermolecular Forces
Intermolecular forces are the forces of attraction and repulsion between molecules that affect their physical properties. There are several types of intermolecular forces, including hydrogen bonds, dipole-dipole interactions, and London dispersion forces. They are crucial in influencing a substance's state of matter at a given temperature, its boiling and melting points, and its solubility. In the context of the pentane isomers, these forces play a key role in determining why each isomer has a distinct boiling point.

For example, the stronger the intermolecular forces within a substance, the more energy it takes to separate the molecules, leading to a higher boiling point. As students, by exploring the connection between molecular structure and intermolecular forces, you gain insights into why substances act the way they do under different conditions, paving the way for deeper understanding of materials and their applications.
London Dispersion Forces
Among the various intermolecular forces, London dispersion forces are a type of force that all molecules experience. They are often the weakest form of intermolecular attraction but are pivotal in nonpolar compounds. These forces arise due to the temporary polarization of electrons within a molecule, which induces a temporary dipole and, consequently, attracts other molecules. The larger the molecule, and the more electrons it has, the stronger the dispersion forces will be.

In the trio of pentane isomers, the shape and size of the molecule influence the strength of these forces. Straight-chain pentane, with its extended structure, allows for more contact between molecules, and thus, experiences stronger London dispersion forces compared to its branched counterparts. Understanding how London dispersion forces work provides a basis for predicting the behavior of other nonpolar molecules and their interactions.
Molecular Structure
Molecular structure denotes the three-dimensional arrangement of atoms within a molecule. It's like the architecture of molecules: the positioning and connections directly affect the molecule's properties and reactivity. For isomers, molecular structure is paramount, as it dictates the physical characteristics and how the molecule interacts with its environment.

The structure determines the molecule's surface area and overall shape, which affects how molecules pack together, their ability to interact with each other, and, ultimately, the strength of intermolecular forces, such as London dispersion forces. In pentane isomers, the straight-chain configuration offers a greater surface area and, consequently, a higher boiling point due to increased intermolecular interactions. In contrast, the more branched neopentane has a lower boiling point because its compact shape limits surface contact between molecules, leading to weaker intermolecular forces. Learning about molecular structure is crucial for understanding how substances may behave similarly or differently under comparable conditions.

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Most popular questions from this chapter

You are given two bottles, each containing a colorless liquid. You are told that one liquid is cyclohexane and the other is benzene. Suggest one chemical test that would enable you to distinguish between these two liquids.

Fats and oils are names for the same class of compounds, called triglycerides, which contain three ester groups in which \(\mathrm{R}, \mathrm{R}^{\prime},\) and \(\mathrm{R}^{\prime \prime}\) represent long hydrocarbon chains. (a) Suggest a reaction that leads to the formation of a triglyceride molecule, starting with glycerol and carboxylic acids (see p. 398 for structure of glycerol). (b) In the old days, soaps were made by hydrolyzing animal fat with lye (a sodium hydroxide solution). Write an equation for this reaction. (c) The difference between fats and oils is that at room temperature, the former are solid and the latter are liquids. Fats are usually produced by animals, whereas oils are commonly found in plants. The melting points of these substances are determined by the number of \(\mathrm{C}=\mathrm{C}\) bonds (or the extent of unsaturation) present- -the larger the number of \(\mathrm{C}=\mathrm{C}\) bonds, the lower the melting point and the more likely the substance is a liquid. Explain. (d) One way to convert liquid oil to solid fat is to hydrogenate the oil, a process by which some or all of the \(\mathrm{C}=\mathrm{C}\) bonds are converted to \(\mathrm{C}-\mathrm{C}\) bonds. This procedure prolongs shelf life of the oil by removing the more reactive \(\mathrm{C}=\mathrm{C}\) group and facilitates packaging. How would you carry out such a process (that is, what reagents and catalyst would you employ)? (e) The degree of unsaturation of oil can be determined by reacting the oil with iodine, which reacts with the \(\mathrm{C}=\mathrm{C}\) as follows: The procedure is to add a known amount of iodine to the oil and allow the reaction to go to completion. The amount of excess (unreacted) iodine is determined by titrating the remaining iodine with a standard sodium thiosulfate \(\left(\mathrm{Na}_{2} \mathrm{~S}_{2} \mathrm{O}_{3}\right)\) solution: $$\mathrm{I}_{2}+2 \mathrm{Na}_{2} \mathrm{~S}_{2} \mathrm{O}_{3} \longrightarrow \mathrm{Na}_{2} \mathrm{~S}_{4} \mathrm{O}_{6}+2 \mathrm{NaI}$$ The number of grams of iodine that reacts with \(100 \mathrm{~g}\) of oil is called the iodine number. In one case, \(43.8 \mathrm{~g}\) of \(\mathrm{I}_{2}\) were treated with \(35.3 \mathrm{~g}\) of corn oil. The excess iodine required \(20.6 \mathrm{~mL}\) of \(0.142 \mathrm{M} \mathrm{Na}_{2} \mathrm{~S}_{2} \mathrm{O}_{3}\) for neutralization. Calculate the iodine number of the corn oil.

Give the chemical names of these organic compounds and write their formulas: marsh gas, grain alcohol, wood alcohol, rubbing alcohol, antifreeze, mothballs, chief ingredient of vinegar.

Like ethylene, tetrafluoroethylene \(\left(\mathrm{C}_{2} \mathrm{~F}_{4}\right)\) undergoes polymerization reaction to form polytetrafluoroethylene (Teflon). Draw a repeating unit of the polymer.

Suggest two chemical tests that would help you distinguish between these two compounds: (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}\)

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