Textbook Question
Under certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium methoxide forms 1-methoxybutane at a rate of 0.05 mol/L per second. What would be the rate if 0.1 M 1-bromobutane and 2.0 M NaOCH3 were used?
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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 11a
Classify each reaction as a substitution, an elimination, or neither. Identify the leaving group in each reaction, and the nucleophile in substitutions.
a. 
Verified step by step guidance1
Identify the type of reaction: The reaction involves the replacement of an iodine atom with an ethoxy group (OCH2CH3), indicating a substitution reaction.
Determine the leaving group: In the given reaction, the iodine atom (I) is the leaving group as it is replaced by the ethoxy group.
Identify the nucleophile: The nucleophile in this reaction is the ethoxide ion (OCH2CH3-) from the sodium ethoxide (Na+ -OCH2CH3).
Analyze the reaction mechanism: This is likely an SN2 reaction because it involves a primary alkyl halide and a strong nucleophile, leading to a direct displacement of the leaving group.
Consider the reaction conditions: The presence of a strong base and a primary substrate supports the SN2 mechanism, where the nucleophile attacks the carbon atom bonded to the leaving group, resulting in the substitution.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Substitution Reaction
A substitution reaction involves the replacement of an atom or a group of atoms in a molecule with another atom or group. In the given reaction, the iodide ion (I-) is replaced by the ethoxy group (OCH2CH3) from sodium ethoxide (Na+ -OCH2CH3), indicating a nucleophilic substitution reaction.
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Recognizing Substitution Reactions.
Leaving Group
A leaving group is an atom or group that can depart with an electron pair, forming a stable species after the departure. In the reaction, the iodide ion (I-) acts as the leaving group, as it detaches from the cyclohexane ring to form sodium iodide (NaI), facilitating the substitution process.
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07:22The 3 important leaving groups to know.
Nucleophile
A nucleophile is a chemical species that donates an electron pair to form a chemical bond in a reaction. In this reaction, the ethoxide ion (OCH2CH3-) from sodium ethoxide acts as the nucleophile, attacking the carbon atom bonded to the iodide ion, leading to the formation of the new ether linkage in the product.
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Related Practice
Textbook Question
Classify each reaction as a substitution, an elimination, or neither. Identify the leaving group in each reaction, and the nucleophile in substitutions.
c.
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Textbook Question
Classify each reaction as a substitution, an elimination, or neither. Identify the leaving group in each reaction, and the nucleophile in substitutions.
b.
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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.
(d)
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.
(c)
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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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