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Chapter 23: Problem 83

Which of the following hydrocarbons has the lowest dipole moment? (a) CC=CC (b) \(\mathrm{CH}_{3}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}\) (d) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{C} \equiv \mathrm{CH}\)

Short Answer

Expert verified
(b) 2-butyne has the lowest dipole moment due to its symmetrical structure.

Step by step solution

01

Identify Molecular Structures

Based on the given SMILES and chemical formulas, identify and sketch each of the hydrocarbon structures. (a) is 2-butene, with the formula \( ext{CH}_3- ext{CH}= ext{CH}- ext{CH}_3\).(b) is 2-butyne, with the formula \( ext{CH}_3- ext{C} ext{C}- ext{CH}_3\).(c) is 1-butene, written as \( ext{CH}_3- ext{CH}_2- ext{CH}= ext{CH}_2\).(d) is vinylacetylene, written as \( ext{CH}_2= ext{CH}- ext{C} ext{C} ext{H}\).
02

Determine Molecular Symmetry

Analyze the symmetry for each hydrocarbon. Highly symmetrical molecules generally have lower dipole moments. (a) 2-butene: Symmetric around the double bond. (b) 2-butyne: Symmetric around the triple bond. (c) 1-butene: Asymmetrical structure. (d) Vinylacetylene: Asymmetrical structure.
03

Assess Molecular Polarity

Evaluate the molecular polarity based on symmetry and bond type. - Symmetrical structures often mean the dipole moments cancel out. - Look for molecular symmetricalness: (a) 2-butene is symmetrical. (b) 2-butyne is symmetrical. (c) 1-butene is asymmetrical. (d) Vinylacetylene is asymmetrical.
04

Compare Dipole Moments

Symmetrical hydrocarbons (a and b) will tend to have much lower dipole moments compared to asymmetrical hydrocarbons (c and d) due to the cancellation of dipole vectors along the molecule.
05

Select the Answer

Identify the molecule with complete symmetrical structure around a nonpolar bond center. Hydrocarbon (b), 2-butyne, has the lowest dipole moment, as the structure is symmetrical with no areas of significant charge distribution.

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Key Concepts

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

Molecular Symmetry
Molecular symmetry is a concept often used in chemistry to explain the distribution of atoms within a molecule. It refers to the consistent arrangement of atoms throughout the molecule, relative to different symmetry points, axes, or planes.

When considering symmetry in molecules such as hydrocarbons, it's important to note:
  • Symmetrical molecules, like 2-butyne, have an even distribution of charges across the molecule due to their symmetry.
  • This type of symmetry effectively cancels out dipole moments, leading to a molecule with a very low or even zero dipole moment.
In hydrocarbons, symmetry arises when the molecule is evenly balanced around specific bonds, like double or triple bonds found in 2-butene and 2-butyne. These molecules maintain their symmetry by having equal atoms or groups on either side of the central bond.
Molecular Polarity
Molecular polarity refers to the distribution of electric charge around a molecule.

When molecules display asymmetrical shapes or possess polar bonds, they exhibit polarity, where charges are unevenly distributed.
  • Polar bonds arise when there is a significant difference in electronegativity between the bonded atoms, causing an unequal sharing of electrons.
  • For symmetrical molecules like 2-butyne, the symmetrical distribution of equivalent groups leads to a cancellation of dipole moments.
  • In asymmetrical molecules such as 1-butene, the uneven placement of atoms leads to a visible dipole moment, making them polar.
Thus, understanding molecular polarity is crucial in predicting the behavior and properties of molecules, such as their solubility and interaction with other molecules in chemical reactions.
Organic Chemistry
Organic chemistry is the study of carbon compounds, mainly hydrocarbons, and other related compounds. It is a vast field that explores the properties, structures, reactions, and synthesis of carbon-containing compounds.

Here are some key aspects:
  • Hydrocarbons, which include alkanes, alkenes, and alkynes, are the simplest organic compounds consisting solely of carbon and hydrogen.
  • In alkenes like 2-butene, double bonds result in specific structural configurations that can affect the molecule's reactivity and polarity.
  • Alkynes such as 2-butyne have triple bonds, which provide rigidity and result in a linear geometry making these molecules highly symmetrical.
Organic chemistry also involves understanding how changes in molecular structure can drastically alter a compound's chemical and physical properties. By studying these properties, chemists learn how to manipulate molecules for various applications, including pharmaceuticals, materials science, and more.

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Most popular questions from this chapter

Which is true regarding the \(\mathrm{HOCH}_{2}-(\mathrm{CHOH})_{4}\) \(-\mathrm{CH}_{2} \mathrm{OH} ?\) (1) the number of racemic mixtures will be four for the compound. (2) the total number of optical isomers is ten and number of meso isomer is two. (3) the total number of optical isomer is sixteen and number of meso isomer is zero. (4) the optically active isomers are eight while meso isomers are two. (a) 1,2 and 3 (b) 2,3 and 4 (c) 1,2 and 4 (d) 1 and 2 only

The number of isomeric ethers corresponding to the formula \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) is

Which class of compound can exhibit geometrical isomerism (a) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{3}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}=\mathrm{NOH}\) (c) O=C(O)C=CC(=O)O (d) All of these

Racemic mixture is formed by mixing two (a) isomeric compounds (b) chiral compounds (c) meso compounds (d) enantiomers with chiral carbon

The \(\mathrm{Cl}-\mathrm{C}-\mathrm{Cl}\) angle in \(1,1,2,2\)-tetrachloroethene and tetrachloromethane will be about (a) \(120^{\circ}\) and \(109.5^{\circ}\) (b) \(90^{\circ}\) and \(109.5^{\circ}\) (c) \(109.5^{\circ}\) and \(90^{\circ}\) (d) \(109.5^{\circ}\) and \(120^{\circ}\)
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