Textbook Question
Draw the two chair conformers for each of the following and indicate which conformer is more stable:
d. cis-1,2-diethylcyclohexane
1
views
Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
Not the one you use?Change textbookSelect a different textbook
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
All textbooks
Bruice 8th EditionCh. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and StructureProblem 75
Bruice 8th EditionCh. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and StructureProblem 75Chapter 4, Problem 75
Why are lower molecular weight alcohols more soluble in water than higher molecular weight alcohols?
Verified step by step guidance1
Consider the structure of alcohols: they have a hydrophilic (water-attracting) hydroxyl group (-OH) and a hydrophobic (water-repelling) hydrocarbon chain.
Understand that solubility in water is influenced by the ability of a substance to form hydrogen bonds with water molecules.
Recognize that lower molecular weight alcohols have shorter hydrocarbon chains, which means the hydrophilic hydroxyl group has a more significant influence on the molecule's overall polarity.
Note that as the hydrocarbon chain length increases in higher molecular weight alcohols, the hydrophobic character of the molecule increases, reducing its overall solubility in water.
Conclude that the balance between the hydrophilic and hydrophobic parts of the molecule determines the solubility, with lower molecular weight alcohols being more soluble due to their relatively larger hydrophilic component.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Was this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Hydrophilicity and Hydrophobicity
Hydrophilicity refers to the affinity of a molecule for water, while hydrophobicity indicates a lack of such affinity. Lower molecular weight alcohols, like methanol and ethanol, have shorter hydrocarbon chains, which makes them more hydrophilic due to their ability to form hydrogen bonds with water. In contrast, higher molecular weight alcohols have longer hydrophobic hydrocarbon chains that reduce their overall solubility in water.
Recommended video:
2:00
Fatty Acids Concept 1
Hydrogen Bonding
Hydrogen bonding is a type of intermolecular force that occurs when a hydrogen atom covalently bonded to a highly electronegative atom, such as oxygen, interacts with another electronegative atom. Lower molecular weight alcohols can form more hydrogen bonds with water molecules due to their smaller size and higher proportion of hydroxyl (-OH) groups, enhancing their solubility. Higher molecular weight alcohols have fewer hydroxyl groups relative to their size, limiting their ability to interact with water.
Recommended video:
Guided course
00:48The definition of hydrogenation.
Molecular Size and Structure
The size and structure of a molecule significantly influence its solubility in water. As the molecular weight of alcohols increases, the hydrophobic hydrocarbon portion becomes more dominant, overshadowing the hydrophilic -OH group. This structural change leads to decreased solubility in water for higher molecular weight alcohols, as the larger hydrophobic regions do not interact favorably with water molecules.
Recommended video:
Guided course
08:41Review of Molecular Orbitals
Related Practice
Textbook Question
How much more stable is the most stable staggered conformer than the most stable eclipsed conformer?
1
views
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
2
views
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
1
views
Textbook Question
Draw the conformer that is present in greatest concentration.
1
views
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.
2
views