Textbook Question
For each of the following compounds, determine whether the cis isomer or the trans isomer is more stable.
a.
b.
c.
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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 76c
Bruice 8th EditionCh. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and StructureProblem 76cChapter 4, Problem 76c
How much more stable is the most stable staggered conformer than the most stable eclipsed conformer?
Verified step by step guidance1
Identify the molecule in question and determine the type of interactions present in both the staggered and eclipsed conformations. For example, in alkanes like ethane, the staggered conformation minimizes torsional strain, while the eclipsed conformation maximizes it.
Understand that the energy difference between staggered and eclipsed conformations arises due to torsional strain. Torsional strain occurs when bonds on adjacent carbons are aligned (eclipsed), leading to repulsion between electron clouds in the bonding orbitals.
Recall that the most stable staggered conformer occurs when bulky groups are positioned as far apart as possible (anti-periplanar), minimizing steric hindrance. The most stable eclipsed conformer occurs when the least sterically hindered groups are aligned.
Use the given or known energy values for the torsional strain of the staggered and eclipsed conformations. For example, in ethane, the energy difference between the staggered and eclipsed conformations is approximately 12 kJ/mol (or 3 kcal/mol).
Calculate the energy difference by subtracting the energy of the most stable staggered conformer from the energy of the most stable eclipsed conformer. This value represents how much more stable the staggered conformer is compared to the eclipsed conformer.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Conformational Isomerism
Conformational isomerism refers to the different spatial arrangements of atoms in a molecule that can be interconverted by rotation around single bonds. In organic chemistry, this concept is crucial for understanding how molecules can adopt various shapes, which significantly influence their stability and reactivity.
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Understanding what a conformer is.
Staggered vs. Eclipsed Conformers
Staggered and eclipsed conformers are two specific arrangements of atoms in a molecule, particularly in alkanes. Staggered conformers have groups positioned as far apart as possible, minimizing steric strain, while eclipsed conformers have groups aligned with each other, leading to increased steric hindrance and higher energy states. This difference in arrangement directly affects the stability of the molecule.
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Stability and Energy in Conformers
The stability of conformers is determined by their potential energy, with lower energy states being more stable. The most stable staggered conformer is significantly lower in energy compared to the most stable eclipsed conformer due to reduced steric interactions. Understanding this energy difference is essential for predicting the behavior and reactivity of organic molecules.
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Related Practice
Textbook Question
How many ethers have molecular formula C5H12O? Draw their structures and give each a systematic name. What are their common names?
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Textbook Question
Draw the conformer that is present in greatest concentration.
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Textbook Question
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.
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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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