Textbook Question
The sulfur and oxygen in methanethiol and methanol are both sp3 hybridized. Why is the S―H bond longer than the O―H bond?
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Ch. 2 - General Chemistry Translated: Finding the Electrons
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. 2 - General Chemistry Translated: Finding the ElectronsProblem 44
Mullins 1st EditionCh. 2 - General Chemistry Translated: Finding the ElectronsProblem 44Chapter 1, Problem 44
A molecular orbital diagram is shown for the C―Cl bond in chloromethane. If two more electrons were added to chloromethane, where would the electrons go?
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Verified step by step guidance1
Step 1: Analyze the molecular orbital diagram provided. The diagram shows the bonding (σ) and antibonding (σ*) molecular orbitals for the C-Cl bond in chloromethane. The bonding orbital (σ) is lower in energy and fully occupied with two electrons, while the antibonding orbital (σ*) is higher in energy and currently unoccupied.
Step 2: Recall the principle of electron filling in molecular orbitals. Electrons fill the lowest available energy orbitals first, following the Aufbau principle. If additional electrons are added to the molecule, they will occupy the next available orbital with the lowest energy.
Step 3: Determine the next available orbital. Since the bonding orbital (σ) is already fully occupied, the next available orbital is the antibonding orbital (σ*), which is higher in energy.
Step 4: Consider the implications of adding electrons to the antibonding orbital. Electrons in antibonding orbitals weaken the bond between the atoms because they counteract the stabilizing effect of electrons in the bonding orbital.
Step 5: Conclude that if two more electrons were added to chloromethane, they would occupy the antibonding orbital (σ*), potentially destabilizing the C-Cl bond.
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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 describes how atomic orbitals combine to form molecular orbitals, which can be occupied by electrons. In this theory, electrons are delocalized over the entire molecule rather than being localized between individual atoms. The energy levels of these molecular orbitals determine the stability and reactivity of the molecule, with bonding orbitals being lower in energy and antibonding orbitals being higher.
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Review of Molecular Orbitals
Electron Configuration in Molecular Orbitals
The electron configuration in molecular orbitals indicates how electrons are distributed among the available molecular orbitals. Electrons fill the lowest energy orbitals first, following the Pauli exclusion principle and Hund's rule. In the case of chloromethane, the molecular orbital diagram shows the placement of electrons in bonding (σ) and antibonding (σ*) orbitals, which is crucial for predicting how additional electrons would be accommodated.
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Bonding and Antibonding Orbitals
Bonding orbitals are formed when atomic orbitals combine constructively, leading to increased electron density between the nuclei, which stabilizes the bond. Antibonding orbitals, indicated by an asterisk (σ*), result from destructive interference and have higher energy, leading to destabilization. When considering the addition of electrons to chloromethane, it is essential to determine whether they will occupy bonding or antibonding orbitals based on their energy levels.
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Related Practice
Textbook Question
Each pair of structures represents two valid resonance structures. Use the arrow-pushing formalism to justify the formation of the one on the left from the one on the right.
(b)
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Textbook Question
Rank the following molecules by the length of the indicated bond from shortest to longest.
(a)
(b)
(c)
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Textbook Question
How might electrons be excited from π to π* based on the molecular orbital diagram shown? [This will be relevant in Chapter 21.]
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Textbook Question
Each pair of structures represents two valid resonance structures. Use the arrow-pushing formalism to justify the formation of the one on the left from the one on the right.
(a)
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Textbook Question
Use hybrid orbitals to draw the following molecules.
(d)
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