Textbook Question
Butadiene, C4H6, is a planar molecule that has the following carbon–carbon bond lengths:
(b) From left to right, what is the hybridization of each carbon atom in butadiene?
Ch.9 - Molecular Geometry and Bonding Theories
Brown14th EditionChemistry: The Central ScienceISBN: 9780134414232
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Table of contents
- Ch.1 - Introduction: Matter, Energy, and Measurement177
- Ch.2 - Atoms, Molecules, and Ions231
- Ch.3 - Chemical Reactions and Reaction Stoichiometry216
- Ch.4 - Reactions in Aqueous Solution189
- Ch.5 - Thermochemistry175
- Ch.6 - Electronic Structure of Atoms168
- Ch.7 - Periodic Properties of the Elements150
- Ch.8 - Basic Concepts of Chemical Bonding177
- Ch.9 - Molecular Geometry and Bonding Theories200
- Ch.10 - Gases179
- Ch.11 - Liquids and Intermolecular Forces113
- Ch.12 - Solids and Modern Materials154
- Ch.13 - Properties of Solutions157
- Ch.14 - Chemical Kinetics199
- Ch.15 - Chemical Equilibrium128
- Ch.16 - Acid-Base Equilibria164
- Ch.17 - Additional Aspects of Aqueous Equilibria163
- Ch.18 - Chemistry of the Environment105
- Ch.19 - Chemical Thermodynamics164
- Ch.20 - Electrochemistry171
- Ch.21 - Nuclear Chemistry122
- Ch.22 - Chemistry of the Nonmetals82
- Ch.23 - Transition Metals and Coordination Chemistry79
- Ch.24 - The Chemistry of Life: Organic and Biological Chemistry16
Brown14th EditionChemistry: The Central ScienceISBN: 9780134414232Not the one you use?Change textbook
Chapter 9, Problem 102c
Butadiene, C4H6, is a planar molecule that has the following carbon–carbon bond lengths:
(c) The middle C¬C bond length in butadiene (1.48 Å) is a little shorter than the average C¬C single bond length (1.54 Å). Does this imply that the middle C¬C bond in butadiene is weaker or stronger than the average C¬C single bond?
Verified step by step guidance1
Understand that bond length is inversely related to bond strength: shorter bonds are generally stronger.
Recognize that the middle C-C bond in butadiene is shorter (1.48 Å) than the average C-C single bond (1.54 Å).
Consider the concept of resonance in butadiene, which can lead to partial double bond character in the middle C-C bond.
Acknowledge that partial double bond character typically results in a bond that is shorter and stronger than a single bond.
Conclude that the middle C-C bond in butadiene is likely stronger than the average C-C single bond due to its shorter length and resonance effects.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Bond Length and Bond Strength
In general, shorter bond lengths indicate stronger bonds due to the increased overlap of atomic orbitals. Conversely, longer bonds tend to be weaker. This relationship is crucial for understanding how bond length can provide insights into the strength of a bond.
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00:36
Average Bond Order
Resonance in Molecules
Butadiene exhibits resonance, where the actual structure is a hybrid of multiple contributing structures. This delocalization of electrons can lead to bond lengths that differ from typical single or double bonds, affecting their strength and stability.
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Comparison of Bond Types
C–C single bonds and double bonds have distinct characteristics. A single bond is generally longer and weaker than a double bond. Understanding these differences helps in analyzing the bond lengths in butadiene and determining the relative strength of the middle C–C bond.
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Related Practice
Textbook Question
The structure of borazine, B3N3H6, is a six-membered ring of alternating B and N atoms. There is one H atom bonded to each B and to each N atom. The molecule is planar. (e) What are the hybridizations at the B and N atoms in the Lewis structures from parts (a) and (b)? Would you expect the molecule to be planar for both Lewis structures? Would you expect the molecule to be planar for both Lewis structures?
Textbook Question
The structure of borazine, B3N3H6, is a six-membered ring of alternating B and N atoms. There is one H atom bonded to each B and to each N atom. The molecule is planar. (a) Write a Lewis structure for borazine in which the formal charge on every atom is zero.
Textbook Question
The structure of borazine, B3N3H6, is a six-membered ring of alternating B and N atoms. There is one H atom bonded to each B and to each N atom. The molecule is planar. (c) What are the formal charges on the atoms in the Lewis structure from part (b)? Given the electronegativities of B and N, do the formal charges seem favorable or unfavorable? What are the formal charges on the atoms in the Lewis structure from part (b)?
Textbook Question
Butadiene, C4H6, is a planar molecule that has the following carbon–carbon bond lengths:
(a) Predict the bond angles around each of the carbon atoms and sketch the molecule.
Textbook Question
In ozone, O3, the two oxygen atoms on the ends of the molecule are equivalent to one another. (d) How many electrons are delocalized in the p system of ozone?