Textbook Question
Draw and name all stereoisomers of 3-chlorohepta-2,4-diene
b. using the E-Z nomenclature.
Ch. 7 - Structure and Synthesis of Alkenes; Elimination
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 7, Problem 46a
For each alkene, indicate the direction of the dipole moment. For each pair, determine which compound has the larger dipole moment.
a. cis-1,2-difluoroethene or trans-1,2-difluoroethene
Verified step by step guidance1
Identify the molecular structure of cis-1,2-difluoroethene and trans-1,2-difluoroethene. In the cis isomer, both fluorine atoms are on the same side of the double bond, while in the trans isomer, they are on opposite sides.
Understand that the dipole moment is a vector quantity that depends on the difference in electronegativity between atoms and the geometry of the molecule. Fluorine is more electronegative than carbon, creating a dipole in the C-F bond.
For cis-1,2-difluoroethene, the dipole moments of the two C-F bonds add up because they are in the same direction, resulting in a net dipole moment pointing from the hydrogen side towards the fluorine side.
For trans-1,2-difluoroethene, the dipole moments of the two C-F bonds cancel each other out because they are in opposite directions, resulting in a net dipole moment of zero.
Compare the net dipole moments: cis-1,2-difluoroethene has a larger dipole moment than trans-1,2-difluoroethene because the dipoles in the trans isomer cancel out, while in the cis isomer, they reinforce each other.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Dipole Moment
The dipole moment is a measure of the separation of positive and negative charges in a molecule. It is a vector quantity, having both magnitude and direction, and is influenced by the electronegativity of atoms and the geometry of the molecule. In alkenes, the dipole moment is determined by the arrangement of substituents around the double bond.
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Cis-Trans Isomerism
Cis-trans isomerism, also known as geometric isomerism, occurs in alkenes due to restricted rotation around the double bond. In cis isomers, similar groups are on the same side of the double bond, while in trans isomers, they are on opposite sides. This spatial arrangement affects the dipole moment, as cis isomers often have a higher dipole moment due to the additive effect of the dipoles.
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Electronegativity
Electronegativity is the tendency of an atom to attract electrons towards itself in a chemical bond. In molecules like difluoroethene, fluorine's high electronegativity creates a polar bond with carbon, contributing to the molecule's overall dipole moment. The difference in electronegativity between bonded atoms is a key factor in determining the direction and magnitude of the dipole moment.
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Related Practice
Textbook Question
Draw and name all stereoisomers of 3-chlorohepta-2,4-diene
a. using the cis-trans nomenclature.
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Textbook Question
For each alkene, indicate the direction of the dipole moment. For each pair, determine which compound has the larger dipole moment.
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Textbook Question
The energy difference between cis- and trans-but-2-ene is about 4 kJ/mol; however, the trans isomer of 4,4-dimethylpent-2-ene is nearly 16 kJ/mol more stable than the cis isomer. Explain this large difference.
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Textbook Question
Cholesterol, C27H46O, has only one pi bond. With no additional information, what else can you say about its structure?
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Textbook Question
For each alkene, indicate the direction of the dipole moment. For each pair, determine which compound has the larger dipole moment
b. cis-1,2-dibromoethene or trans-2,3-dibromobut-2-ene
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