Textbook Question
How much more stable is the most stable staggered conformer than the most stable eclipsed conformer?
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Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and StructureProblem 76a
Bruice 8th EditionCh. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and StructureProblem 76aChapter 4, Problem 76a
Draw a potential energy diagram for rotation about the C¬C bond of 1,2-dichloroethane through 360°, starting with the least stable conformer. The anti conformer is 1.2 kcal/mol more stable than a gauche conformer. A gauche conformer has two energy barriers, 5.2 kcal/mol and 9.3 kcal/mol.
Verified step by step guidance1
Step 1: Understand the problem. The goal is to draw a potential energy diagram for the rotation about the C-C bond in 1,2-dichloroethane through 360°. The diagram should reflect the energy changes as the molecule rotates, starting with the least stable conformer. Key information includes the anti conformer being 1.2 kcal/mol more stable than the gauche conformer, and the energy barriers for the gauche conformer being 5.2 kcal/mol and 9.3 kcal/mol.
Step 2: Identify the conformers. The anti conformer has the two chlorine atoms on opposite sides of the molecule, making it the most stable due to minimized steric hindrance. The gauche conformers have the chlorine atoms closer together, leading to steric interactions and higher energy. There are two gauche conformers due to the symmetry of the molecule.
Step 3: Determine the energy levels. Assign the anti conformer a baseline energy level (e.g., 0 kcal/mol). The gauche conformers are 1.2 kcal/mol higher in energy than the anti conformer. The energy barriers for rotation are given as 5.2 kcal/mol and 9.3 kcal/mol, which correspond to the transition states encountered during rotation.
Step 4: Sketch the potential energy diagram. On the x-axis, represent the dihedral angle of rotation (0° to 360°). On the y-axis, represent the potential energy in kcal/mol. Start with the least stable conformer (highest energy gauche conformer) and plot the energy changes as the molecule rotates through the anti conformer and other gauche conformer, including the energy barriers at the transition states.
Step 5: Label the diagram. Clearly mark the anti conformer, gauche conformers, and transition states with their respective energy values. Indicate the dihedral angles where each conformer and transition state occurs (e.g., 0°, 120°, 240°, 360°). Ensure the diagram reflects the periodic nature of rotation and the energy differences provided in the problem.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Potential Energy Diagrams
A potential energy diagram visually represents the energy changes of a system as it undergoes a transformation, such as rotation around a bond. In organic chemistry, these diagrams help illustrate the stability of different conformers and the energy barriers associated with interconversions. The y-axis typically represents potential energy, while the x-axis shows the degree of rotation, allowing for a clear understanding of the energy landscape.
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Conformational Analysis
Conformational analysis involves studying the different spatial arrangements of a molecule that can be achieved by rotation around single bonds. In the case of 1,2-dichloroethane, the anti and gauche conformers represent two distinct arrangements, with the anti conformer being more stable due to less steric hindrance. Understanding these conformers is crucial for predicting the molecule's behavior and reactivity.
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Energy Barriers
Energy barriers are the energy differences that must be overcome for a molecule to transition from one conformer to another. In the context of 1,2-dichloroethane, the specified barriers of 5.2 kcal/mol and 9.3 kcal/mol indicate the energy required to move from the gauche conformer to higher energy states. These barriers are essential for understanding the stability of conformers and the kinetics of conformational changes.
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Related Practice
Textbook Question
Draw the two chair conformers for each of the following and indicate which conformer is more stable:
e. cis-1-ethyl-3-isopropylcyclohexane
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Textbook Question
Draw the two chair conformers for each of the following and indicate which conformer is more stable:
f. cis-1-ethyl-4-isopropylcyclohexane
1217
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Textbook Question
Draw the conformer that is present in greatest concentration.
1224
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Textbook Question
How much more stable is the most stable staggered conformer than the least stable eclipsed conformer?
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Textbook Question
Why are lower molecular weight alcohols more soluble in water than higher molecular weight alcohols?
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