Textbook Question
Show how you might use SN2 reactions to convert 1-chlorobutane into the following compounds.
a. butan-1-ol
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Ch.6 - Alkyl Halides; Nucleophilic Substitution
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 6, Problem 6c
For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.
c. 1-bromobutane and 1-chlorobutane
Verified step by step guidance1
Identify the two compounds in question: 1-bromobutane and 1-chlorobutane. These are alkyl halides where bromine and chlorine are attached to a butane chain.
Consider the molecular weight of each compound. 1-bromobutane has a higher molecular weight than 1-chlorobutane because bromine is heavier than chlorine.
Analyze the intermolecular forces present. Both compounds exhibit van der Waals forces, but 1-bromobutane will have stronger dispersion forces due to its larger electron cloud compared to 1-chlorobutane.
Check the boiling points in the provided table. 1-bromobutane has a boiling point of 102°C, while 1-chlorobutane has a boiling point of 78°C.
Explain the difference in boiling points: The higher boiling point of 1-bromobutane is due to its greater molecular weight and stronger dispersion forces, which require more energy to overcome during the phase transition from liquid to gas.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Boiling Point
The boiling point of a compound is the temperature at which its vapor pressure equals the external pressure, causing it to change from liquid to gas. It is influenced by intermolecular forces, molecular weight, and structural characteristics. Generally, compounds with stronger intermolecular forces, such as hydrogen bonding or dipole-dipole interactions, exhibit higher boiling points.
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Intermolecular Forces
Intermolecular forces are the forces of attraction or repulsion between molecules. The main types include London dispersion forces, dipole-dipole interactions, and hydrogen bonding. In the case of halogenated compounds like 1-bromobutane and 1-chlorobutane, the strength of these forces significantly affects their boiling points, with stronger dipole-dipole interactions leading to higher boiling points.
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Molecular Weight
Molecular weight, or molar mass, is the mass of a molecule calculated as the sum of the atomic weights of its constituent atoms. Generally, as molecular weight increases, the boiling point tends to increase due to the greater surface area and stronger London dispersion forces. In comparing 1-bromobutane and 1-chlorobutane, the difference in molecular weights contributes to their boiling point differences.
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Related Practice
Textbook Question
For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.
b. isopropyl chloride and tert-butyl bromide
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Textbook Question
Show how free-radical halogenation might be used to synthesize the following compounds. In each case, explain why we expect to get a single major product.
(a) 1-chloro-2,2-dimethylpropane (neopentyl chloride)
(b) 2-bromo-2-methylbutane
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Textbook Question
Show how you might use SN2 reactions to convert 1-chlorobutane into the following compounds.
b. 1-fluorobutane
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Textbook Question
The light-initiated reaction of 2,3-dimethylbut-2-ene with N-bromosuccinimide (NBS) gives two products:
a. Give a mechanism for this reaction, showing how the two products arise as a consequence of the resonance-stabilized intermediate.
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Textbook Question
The light-initiated reaction of 2,3-dimethylbut-2-ene with N-bromosuccinimide (NBS) gives two products:
b. The bromination of cyclohexene using NBS gives only one major product, as shown on the previous page. Explain why there is no second product from an allylic shift.
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