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Chapter 13: Problem 16

Arrange \(2,2,3\) -trimethylpentane, 1 -propanol, toluene \(\left(\mathrm{C}_{7} \mathrm{H}_{8}\right)\), and dimethyl sulfoxide \(\left[\left(\mathrm{CH}_{3}\right)_{2} S=0\right]\) in order of increasing dipole moment. Explain your reasoning.

Short Answer

Expert verified
Arrange as follows: 2,2,3-trimethylpentane < toluene < 1-propanol < dimethyl sulfoxide (increasing dipole moment).

Step by step solution

01

Understand Dipole Moments

Dipole moment is a measure of the separation of positive and negative charges in a molecule. The greater the difference in electronegativity between atoms and the more asymmetric the molecule, the higher the dipole moment.
02

Analyze Molecular Structures

Examine each given compound's molecular geometry. Non-polar molecules like toluene (a hydrocarbon) have symmetric structures, potentially low or zero dipole moments. Conversely, molecules with a strong presence of polar bonds (such as those containing O or highly electronegative atoms like Cl) tend to have higher dipole moments.
03

Determine Individual Dipole Moments for Molecules

- **2,2,3-trimethylpentane**: It's a hydrocarbon, which means it has a very low or essentially zero dipole moment due to its non-polar C-H bonds. - **1-propanol**: Contains an O-H bond which is highly polar, giving this molecule a notable dipole moment. - **Toluene**: Mostly non-polar due to its hydrocarbon structure, but the slightly higher dipole moment might occur because of the unsymmetrically substituted methyl group. - **Dimethyl sulfoxide (DMSO)**: Contains a strongly polar S=O bond, resulting in a high dipole moment.
04

Arrange Based on Dipole Moments

Based on the structural analysis, the order of increasing dipole moment is: 1. 2,2,3-trimethylpentane (lowest dipole moment, non-polar) 2. Toluene (mostly non-polar with slightly polar methyl effect) 3. 1-propanol (polar O-H bond) 4. Dimethyl sulfoxide (highest dipole moment due to S=O bond)

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Key Concepts

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

Molecular Geometry
Molecular geometry refers to the three-dimensional arrangement of atoms in a molecule. It's like a snapshot of how a molecule looks in space. Why is this important? It helps determine how a molecule behaves, especially its physical and chemical properties like polarity and reactivity.
  • Symmetrical molecules tend to be non-polar. This is because the attractive forces are balanced out, resulting in little to no dipole moment.
  • Asymmetrical molecules, on the other hand, may have areas of partial positive and negative charges, increasing their dipole moments.
When analyzing molecular geometry, look at the arrangement of the bonded atoms and the lone pairs. For instance, in 1-propanol, the OH group creates an asymmetrical geometry, resulting in a dipole moment which contributes to its polar nature.
Electronegativity
Electronegativity is a property of atoms that measures their tendency to attract and bond with electrons. Think of it like a tug-of-war between atoms where the stronger one wins more electron density.
  • Higher electronegativity means stronger pull on electrons, often making the molecule polar.
  • Oxygen (O) is more electronegative than most other elements, which is why O-H bonds in compounds like 1-propanol are highly polar.
  • The electronegativity difference between bonded atoms determines the bond type: non-polar covalent (small difference) or polar covalent (large difference).
Understanding electronegativity helps explain the behavior of dimethyl sulfoxide (DMSO) too. The S=O bond showcases a significant electronegativity difference, contributing to its large dipole moment.
Polar Bonds
A polar bond forms when two atoms with different electronegativities share electrons unequally, creating a separation of charge. It鈥檚 like balancing on a seesaw where one side is heavier.
  • These bonds are fundamental in determining molecular polarity.
  • For instance, in 1-propanol, the O-H bond is polar because oxygen attracts the shared electrons more than hydrogen, resulting in a partial negative charge near the oxygen.
  • In DMSO, the S=O bond is another example of a polar bond, which adds to the molecule鈥檚 significant dipole moment.
By identifying polar bonds, one can predict if a molecule will have an overall dipole moment, which can affect its boiling point, solubility, and interactions with other chemicals.
Chemical Structure
Chemical structure defines the arrangement of atoms within a molecule and informs us about how molecules are built and how they might react chemically.
  • This structure is central to understanding molecular properties like stability and reactivity, as well as dipole moments.
  • For hydrocarbons like 2,2,3-trimethylpentane and toluene, the structure is mostly symmetrical, resulting in non-polarity and very low or zero dipole moment.
  • Molecules like DMSO have strong differences in electronegativity between atoms (such as in S=O) and an asymmetric structure, giving rise to a high dipole moment.
Knowing the chemical structure allows us to infer if a molecule is more or less likely to mix with polar or non-polar substances, playing a key role in fields ranging from pharmaceuticals to materials science.

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Most popular questions from this chapter

Under what conditions are molality and molarity likely to be equal? Is the difference between the two greater when water is the solvent or when the solvent is not water? Why?

When water is mixed with a solvent with which it is immiscible, the two liquids usually form two separate layers. If the density of the nonaqueous solvent is \(1.75 \mathrm{~g} / \mathrm{mL}\) at room temperature, sketch the appearance of the heterogeneous mixture in a beaker and label which layer is which. If you were not sure of the density and the identity of the other liquid, how might you be able to identify which is the aqueous layer?

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