Textbook Question
Suggest an alkene to undergo hydroboration–oxidation (1. BH3 2. NaOH, H2O2) to give exclusively the alcohols shown. Pay close attention to the relative (but not absolute) stereochemical outcome.
(b)
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Ch. 8 - Alkenes I: Properties and Electrophilic Additions
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
Chapter 7, Problem 8
Draw the molecular orbital picture of trans-but-2-ene.
Verified step by step guidance1
Start by identifying the molecular structure of trans-but-2-ene. It is a four-carbon alkene with a double bond between carbons 2 and 3, and the two substituents on the double-bonded carbons are on opposite sides (trans configuration).
Determine the type of orbitals involved in the bonding. The double bond consists of one sigma (σ) bond formed by the overlap of sp² hybrid orbitals and one pi (π) bond formed by the side-by-side overlap of unhybridized p orbitals.
Draw the sigma framework first. Each carbon atom in the molecule is sp² hybridized, so three sp² orbitals on each carbon form sigma bonds: one with a hydrogen atom, one with another carbon atom, and one with the adjacent carbon in the double bond.
Next, represent the pi bond. The unhybridized p orbitals on carbons 2 and 3 overlap laterally to form the π bond. Ensure that the p orbitals are shown perpendicular to the plane of the molecule, as this is a key feature of π bonding.
Finally, label the molecular orbitals. The bonding molecular orbital (π) is formed by the in-phase overlap of the p orbitals, while the antibonding molecular orbital (π*) is formed by the out-of-phase overlap. Indicate the relative energy levels of these orbitals, with π being lower in energy than π*.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Molecular Orbitals
Molecular orbitals (MOs) are formed by the combination of atomic orbitals when atoms bond together. In the case of trans-but-2-ene, the MOs help describe the distribution of electrons in the molecule, which influences its stability and reactivity. Understanding how these orbitals overlap is crucial for visualizing the bonding and electronic structure of the compound.
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Trans Configuration
Trans configuration refers to the arrangement of substituents across a double bond in a molecule. For trans-but-2-ene, the two methyl groups are positioned on opposite sides of the double bond, which affects the molecule's physical properties, such as boiling point and polarity. Recognizing this configuration is essential for accurately drawing its molecular orbital picture.
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Hybridization
Hybridization is the concept of mixing atomic orbitals to form new hybrid orbitals that can accommodate bonding. In trans-but-2-ene, the carbon atoms undergo sp² hybridization, resulting in three sp² hybrid orbitals for sigma bonding and one unhybridized p orbital for pi bonding. This understanding is vital for constructing the molecular orbital diagram and predicting the molecule's geometry.
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Related Practice
Textbook Question
What is the index of hydrogen deficiency for each of the following molecular formulas?
(c) C8H14Cl2
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Textbook Question
Provide the IUPAC names for the following alkenes.
(a)
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Textbook Question
What is the index of hydrogen deficiency for each of the following molecular formulas?
(d) C9H12N2O2
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Textbook Question
What is the index of hydrogen deficiency for each of the following molecular formulas?
(e) C6H12O2
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Textbook Question
Provide the expected product for the reaction of each of the following alkenes with H₂SO₄ and H₂O.
(d)
3
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