Textbook Question
There were actually two possible products in the solvolysis reaction from Figure 21.10. Show both products. Which would you expect to be more stable? Why?
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Ch. 21 - Conjugated Systems I: Stability and Addition Reactions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
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Mullins 1st EditionCh. 21 - Conjugated Systems I: Stability and Addition ReactionsProblem 12
Mullins 1st EditionCh. 21 - Conjugated Systems I: Stability and Addition ReactionsProblem 12Chapter 20, Problem 12
Suppose a molecule is formed by the overlap of 16 atomic orbitals.
(a) How many molecular orbitals will be present?
(b) How many will be bonding?
(c) How many will be antibonding?
Verified step by step guidance1
Step 1: Recall the principle of molecular orbital theory, which states that when atomic orbitals combine, they form an equal number of molecular orbitals. If 16 atomic orbitals overlap, there will be 16 molecular orbitals formed.
Step 2: Understand that molecular orbitals are classified as bonding, antibonding, or non-bonding. Bonding orbitals are lower in energy, while antibonding orbitals are higher in energy. Non-bonding orbitals, if present, remain at the same energy level as the atomic orbitals.
Step 3: For a simple system with no non-bonding orbitals, the molecular orbitals are evenly split into bonding and antibonding orbitals. Therefore, half of the molecular orbitals will be bonding, and the other half will be antibonding.
Step 4: Calculate the number of bonding orbitals by dividing the total number of molecular orbitals by 2. For 16 molecular orbitals, the number of bonding orbitals is 16 ÷ 2 = 8.
Step 5: Similarly, calculate the number of antibonding orbitals, which is also 16 ÷ 2 = 8. Thus, there are 8 bonding orbitals and 8 antibonding orbitals in this system.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Molecular Orbital Theory
Molecular Orbital Theory explains how atomic orbitals combine to form molecular orbitals, which can be occupied by electrons. When atomic orbitals overlap, they create a number of molecular orbitals equal to the number of atomic orbitals combined. These molecular orbitals can be classified as bonding or antibonding based on their energy levels and stability.
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Bonding and Antibonding Orbitals
Bonding orbitals are formed when atomic orbitals combine constructively, leading to a lower energy state and increased stability for the molecule. In contrast, antibonding orbitals result from destructive interference of atomic orbitals, resulting in a higher energy state that destabilizes the molecule. The number of bonding and antibonding orbitals can be determined based on the specific interactions of the atomic orbitals involved.
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Conservation of Orbitals
The principle of conservation of orbitals states that the total number of molecular orbitals formed is equal to the total number of atomic orbitals that combine. For example, if 16 atomic orbitals overlap, 16 molecular orbitals will be created. These can be further divided into bonding and antibonding orbitals, typically with half being bonding and half being antibonding, depending on the specific molecular structure.
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Related Practice
Textbook Question
The molecular orbital picture of H2 can be represented by the following diagram. Label σ and σ* on the diagram—that is, which is (a) and which is (b)? Which is lower in energy? Why?
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Textbook Question
p-Nitrophenol (pKa = 7.2) is ten times more acidic than m-nitrophenol (pKa = 8.4) Explain.
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Textbook Question
Hexa-1,3,5-triene uses six p orbitals, each containing a single electron, to make its three π bonds. How many total molecular orbitals are made by the six p orbitals?
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Textbook Question
Why is this not a viable representation of the ψ2, molecular orbital of buta-1,3-diene?
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Textbook Question
Hydroboration, an electrophilic addition reaction like those studied in Section 21.4, only gives 1,2-addition to buta-1,3-diene, regardless of temperature. Why?
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