Textbook Question
Draw Newman projections of the following molecules viewed from the direction of the blue arrows.
(b)
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Ch.3 - Structure and Stereochemistry of Alkanes
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 3, Problem 10a
List each set of compounds in order of increasing boiling point.
a. hexane, octane, and decane
Verified step by step guidance1
Understand that boiling point is influenced by molecular weight and intermolecular forces. In alkanes, as the molecular weight increases, the boiling point generally increases due to stronger van der Waals forces.
Identify the molecular formula for each compound: hexane (C₆H₁₄), octane (C₈H₁₈), and decane (C₁₀H₂₂).
Recognize that these compounds are all alkanes, which are nonpolar and primarily exhibit van der Waals forces. The longer the carbon chain, the greater the surface area for these forces, leading to a higher boiling point.
Compare the molecular weights: hexane has the lowest molecular weight, followed by octane, and then decane, which has the highest molecular weight.
Arrange the compounds in order of increasing boiling point based on their molecular weights: hexane < octane < decane.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Boiling Point
Boiling point is the temperature at which a substance transitions from a liquid to a gas. It is influenced by molecular weight, intermolecular forces, and molecular structure. In organic compounds, longer carbon chains typically result in higher boiling points due to increased van der Waals forces.
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Intermolecular Forces
Intermolecular forces are the forces that hold molecules together, affecting properties like boiling point. In hydrocarbons, van der Waals forces (dispersion forces) are predominant. These forces increase with molecular size, leading to higher boiling points for larger molecules.
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Molecular Size and Structure
Molecular size and structure significantly impact boiling points. In alkanes, as the number of carbon atoms increases, the molecular size grows, enhancing van der Waals forces. Thus, among hexane, octane, and decane, decane has the highest boiling point due to its larger size.
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Related Practice
Textbook Question
Draw the structures of the following compounds.
c. 3,3-diethyl-4-(2,2-dimethylpropyl)octane
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Textbook Question
List each set of compounds in order of increasing boiling point.
b. Octane, (CH3)3C—C(CH3)3 and CH3CH2C(CH3)2CH2CH2CH3
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Textbook Question
Without looking at the structures, give molecular formulas for the compounds: (a) 4-(1,1-dimethylethyl)octane and (b) 5-(1,2,2-trimethylpropyl)nonane. Use the names of the groups to determine the number of carbon atoms; then use the (2n + 2) rule.
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Textbook Question
Draw Newman projections of the following molecules viewed from the direction of the blue arrows.
(a)
1
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Textbook Question
Draw the structures of the following compounds.
b. 5-(1,2,2-trimethylpropyl)nonane
1
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