Chapter 4: Problem 120
The molecules that will have dipole moment: (1) 2, 2-dimethylpropane (2) Trans-1-pent-2-ene (3) Cis-hex-3-ene (4) 2, 2, 3, 3-tetramethylbutane (a) 2,3 (b) 1,3 (c) \(1,2,3\) (d) all of these
Short Answer
Expert verified
(b) 1,3 only cis-hex-3-ene has a dipole moment.
Step by step solution
01
Understand Dipole Moment
Dipole moment arises when there is an asymmetrical charge distribution within a molecule. This typically happens when there are polar bonds and asymmetrical geometries (no symmetry that cancels polarity out). We need to check each given molecule for these features.
02
Analyze 2,2-Dimethylpropane
2,2-Dimethylpropane is a branch-structured hydrocarbon with plenty of symmetry, as all of its C-C bonds and C-H bonds are nonpolar. Therefore, this molecule is nonpolar and has a dipole moment of zero.
03
Analyze Trans-1-Pent-2-ene
Trans isomers have a symmetry that often cancels out their dipole moments. In trans-1-pent-2-ene, the large groups are across from each other on the double bond, leading to symmetric charge distribution and no overall dipole moment.
04
Analyze Cis-Hex-3-ene
Cis isomers do not have symmetry that cancels out dipole moments because groups are on the same side of the double bond. In cis-hex-3-ene, the positioning causes an asymmetrical distribution of charge, resulting in a net dipole moment.
05
Analyze 2,2,3,3-Tetramethylbutane
Like 2,2-dimethylpropane, 2,2,3,3-tetramethylbutane is highly symmetrical. All the substituents are arranged symmetrically, and the molecule is nonpolar with a net dipole moment of zero.
06
Determine Which Have a Dipole Moment
From the analysis, the molecules with dipole moments are those that lack symmetry that can cancel out polarity. Only cis-hex-3-ene fits this description, as it has an asymmetrical charge distribution.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Molecular Symmetry
Understanding molecular symmetry is crucial in determining if a molecule has a dipole moment. A molecule is symmetrical when its parts are arranged in a balanced way around a central point or along a central axis. This symmetry can greatly influence the molecule's properties. When a molecule is symmetrical, the forces or charges may cancel out.
For instance:
For instance:
- In symmetrical molecules, like 2,2-dimethylpropane and 2,2,3,3-tetramethylbutane, the symmetry ensures that any charge distribution is evenly spread, leading to a net dipole moment of zero.
- For asymmetrical molecules, the charge distribution is uneven, leading to a net dipole moment. This is seen in cis-hex-3-ene, where the lack of symmetry results in a molecule that has a dipole moment due to an uneven charge distribution.
Polar Bonds
Polar bonds occur when there is a difference in electronegativity between two bonded atoms. Electronegativity is a measure of how strongly an atom attracts electrons in a bond. When an atom with a higher electronegativity bonds with one of lower electronegativity, electrons tend to be more pulled towards the more electronegative atom, creating a polar bond.
Key points about polar bonds:
Key points about polar bonds:
- Polar bonds have a dipole, where one end is slightly positive (less electronegative atom) and the other is slightly negative (more electronegative atom).
- These types of bonds contribute to the overall dipole moment of a molecule. If polar bonds are symmetrically arranged, their effects may cancel out, resulting in a nonpolar molecule despite the presence of polar bonds.
- In molecules like cis-hex-3-ene, the polar bonds contribute to a net dipole moment because their asymmetrical arrangement prevents cancellation.
- In symmetric molecules like trans-1-pent-2-ene, any polarity in individual bonds is canceled, rendering the overall molecule nonpolar.
Cis-Trans Isomerism
Cis-trans isomerism is a type of stereoisomerism found in alkenes, where similar groups are positioned differently around a double bond. This bonding creates two possibilities: **cis**, where similar groups are on the same side, and **trans**, where they are on opposite sides.
Differences between cis and trans isomers:
Differences between cis and trans isomers:
- **Cis isomers** can result in a polar molecule due to asymmetrical arrangement. For example, in cis-hex-3-ene, substituents are on the same side of the double bond, causing an uneven charge distribution and resulting in a dipole moment.
- **Trans isomers,** like trans-1-pent-2-ene, often lead to nonpolar molecules because the placement of groups across the double bond balances out any charge distribution, often leading to no net dipole moment.