Textbook Question
A common form of elemental phosphorus is the tetrahedral P4 molecule, where all four phosphorus atoms are equivalent:
(b) How many P-P bonds are there in the molecule?
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Ch.8 - Basic Concepts of Chemical Bonding
Brown15th EditionChemistry: The Central ScienceISBN: 9780137542970
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Table of contents
- Ch.1 - Introduction: Matter, Energy, and Measurement111
- Ch.2 - Atoms, Molecules, and Ions166
- Ch.3 - Chemical Reactions and Reaction Stoichiometry138
- Ch.4 - Reactions in Aqueous Solution127
- Ch.5 - Thermochemistry104
- Ch.6 - Electronic Structure of Atoms109
- Ch.7 - Periodic Properties of the Elements107
- Ch.8 - Basic Concepts of Chemical Bonding102
- Ch.9 - Molecular Geometry and Bonding Theories120
- Ch.10 - Gases122
- Ch.11 - Liquids and Intermolecular Forces79
- Ch.12 - Solids and Modern Materials102
- Ch.13 - Properties of Solutions99
- Ch.14 - Chemical Kinetics153
- Ch.15 - Chemical Equilibrium83
- Ch.16 - Acid-Base Equilibria109
- Ch.17 - Additional Aspects of Aqueous Equilibria117
- Ch.18 - Chemistry of the Environment60
- Ch.19 - Chemical Thermodynamics109
- Ch.20 - Electrochemistry113
- Ch.21 - Nuclear Chemistry79
- Ch.22 - Chemistry of the Nonmetals52
- Ch.23 - Transition Metals and Coordination Chemistry57
- Ch.24 - The Chemistry of Life: Organic and Biological Chemistry7
Brown15th EditionChemistry: The Central ScienceISBN: 9780137542970Not the one you use?Change textbook
Chapter 8, Problem 98b
Ortho-Dichlorobenzene, C6H4Cl2, is obtained when two of the adjacent hydrogen atoms in benzene are replaced with Cl atoms. A skeleton of the molecule is shown here. (b) Are there any resonance structures for the molecule? If so, sketch them.
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Ortho-Dichlorobenzene is a derivative of benzene where two adjacent hydrogen atoms are replaced by chlorine atoms, resulting in the molecular formula C_6H_4Cl_2.
In benzene, resonance structures arise due to the delocalization of electrons within the conjugated pi system of the carbon ring.
For ortho-dichlorobenzene, the presence of chlorine atoms affects the electron distribution, but the basic benzene ring structure still allows for resonance.
To determine if resonance structures exist, consider the movement of pi electrons around the benzene ring, keeping in mind that the chlorine atoms can participate in resonance due to their lone pairs.
Sketch the resonance structures by showing the possible locations of double bonds and the delocalization of electrons, ensuring that the overall structure maintains the aromatic stability of the benzene ring.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Resonance Structures
Resonance structures are different ways of drawing a molecule that represent the same arrangement of atoms but differ in the distribution of electrons. In molecules like ortho-dichlorobenzene, resonance helps to illustrate how electrons are delocalized across the structure, affecting stability and reactivity. These structures are not real, but rather a way to visualize the electron distribution in a molecule.
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Resonance Structures
Delocalization of Electrons
Delocalization of electrons refers to the phenomenon where electrons are not confined to a single bond or atom but are spread out over several atoms. In ortho-dichlorobenzene, the presence of resonance allows for the electrons in the π system to be shared among multiple carbon atoms, which contributes to the molecule's stability and influences its chemical properties.
Molecular Geometry and Hybridization
Molecular geometry and hybridization describe the spatial arrangement of atoms in a molecule and the mixing of atomic orbitals to form new hybrid orbitals. In ortho-dichlorobenzene, the carbon atoms are sp² hybridized, leading to a planar structure that allows for effective overlap of p orbitals, facilitating resonance. Understanding these concepts is crucial for visualizing the molecule's shape and predicting its behavior in chemical reactions.
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Related Practice
Textbook Question
Mothballs are composed of naphthalene, C10H8, a molecule that consists of two six-membered rings of carbon fused along an edge, as shown in this incomplete Lewis structure:
(c) Not all of the C—C bond lengths in naphthalene are equivalent. Based on your resonance structures, how many C—C bonds in the molecule do you expect to be shorter than the others?
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Textbook Question
A common form of elemental phosphorus is the tetrahedral P4 molecule, where all four phosphorus atoms are equivalent:
Draw a Lewis structure for a linear P4 molecule that satisfies the octet rule. Does this molecule have resonance structures?
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Textbook Question
Ortho-Dichlorobenzene, C6H4Cl2, is obtained when two of the adjacent hydrogen atoms in benzene are replaced with Cl atoms. A skeleton of the molecule is shown here. (a) Complete a Lewis structure for the molecule using bonds and electron pairs as needed.
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Textbook Question
Two compounds are isomers if they have the same chemical formula but different arrangements of atoms. Use Table 8.3 to estimate H for each of the following gas-phase isomerization reactions and indicate which isomer has the lower enthalpy. (d) Methyl isocyanide → Acetonitrile
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Textbook Question
Mothballs are composed of naphthalene, C10H8, a molecule that consists of two six-membered rings of carbon fused along an edge, as shown in this incomplete Lewis structure:
(b) Do you expect the C—C bond lengths in the molecule to be similar to those of C—C single bonds, C ═C double bonds, or intermediate between C—C single and C ═C double bonds?
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