Textbook Question
Each of the following proposed mechanisms for the free-radical chlorination of methane is wrong. Explain how the experimental evidence disproves each mechanism.
b.
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Ch.4 - The Study of Chemical Reactions
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 4, Problem 4
The reaction of tert-butyl chloride with methanol(CH3)3C—Cl Tert-butylchloride + CH3—OH methanol —> (CH3)C—OCH3 methyltert-butylether + HCl is found to follow the rate equation rate= Kt[(CH3)3C—Cl] a. What is the kinetic order with respect to tert-butyl chloride?
Verified step by step guidance1
Identify the given rate equation: \( \text{rate} = k_t[(\text{CH}_3)_3\text{C—Cl}] \).
Recognize that the rate equation shows the dependence of the reaction rate on the concentration of tert-butyl chloride.
Notice that the rate equation only includes the concentration of tert-butyl chloride, \((\text{CH}_3)_3\text{C—Cl}\), and no other reactants.
Determine the kinetic order with respect to tert-butyl chloride by examining the exponent of its concentration in the rate equation.
Conclude that the kinetic order with respect to tert-butyl chloride is the exponent of its concentration in the rate equation, which is 1.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Kinetics and Rate Laws
Kinetics is the study of the rates of chemical reactions. A rate law expresses the relationship between the rate of a reaction and the concentration of its reactants. The rate equation provided indicates that the rate of the reaction depends only on the concentration of tert-butyl chloride, which is crucial for determining the reaction's order.
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Reaction Order
The reaction order is the exponent to which the concentration of a reactant is raised in the rate law. It indicates how the rate of reaction changes with varying concentrations of reactants. In this case, since the rate equation is first-order with respect to tert-butyl chloride, it means that doubling the concentration of tert-butyl chloride will double the reaction rate.
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Unimolecular Reactions
Unimolecular reactions involve a single reactant molecule undergoing a transformation, often leading to a product without the need for a second reactant. The reaction of tert-butyl chloride with methanol is likely unimolecular, as indicated by the first-order rate law, suggesting that the rate is determined solely by the concentration of tert-butyl chloride.
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Related Practice
Textbook Question
Deuterium (D) is the hydrogen isotope of mass number 2, with a proton and a neutron in its nucleus. The chemistry of deuterium is nearly identical to the chemistry of hydrogen, except that the C―D bond is slightly stronger than the C―H bond by 5.0 kJ/mol (1.2 kcal/mol). Reaction rates tend to be slower when a C―D bond (as opposed to a C―H bond) is broken in a rate-limiting step.This effect, called a kinetic isotope effect, is clearly seen in the chlorination of methane. Methane undergoes free-radical chlorination 12 times as fast as tetradeuteriomethane (CD4)Faster: CH4 + Cl⋅ —> CH3Cl + HCl relative rate= 12Slower: CD4 + Cl⋅ —> CD3Cl + DClrelative rate= 1 c. Consider the thermodynamics of the chlorination of methane and the chlorination of ethane, and use the Hammond postulate to explain why one of these reactions has a much larger isotope effect than the other.
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Textbook Question
Use bond-dissociation enthalpies [TABLE 4-2], p. 167) to calculate values of ΔH° for the following reactions.a. CH3—CH3 + I2 —> CH3CH2I + HI
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Textbook Question
The bromination of methane proceeds through the following steps:1. Br2 + 2 Br• ΔH° (per mole)/+190 kJ (45 kcal)Ea (per mole)/ 190 kJ (45 kcal)2. CH4 + Br• —> CH3+ HBr +73 kJ (17 kcal) 79 kJ (19 kcal) 3. • CH3 + Br2 —> CH3Br + Br -112 kJ (-27 kcal) 4 kJ (1 kcal) d. Compute the overall value of ΔH° for the bromination
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Textbook Question
Each of the following proposed mechanisms for the free-radical chlorination of methane is wrong. Explain how the experimental evidence disproves each mechanism.
a.
1
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Textbook Question
How could an industrial plant control the proportions of methane and chlorine to favor production of CCl4? To favor production of CH3Cl?
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