Textbook Question
a. Propose a mechanism for the free-radical chlorination of ethane,
2
views
Ch.4 - The Study of Chemical Reactions
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
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 11a
The reaction of tert-butyl chloride with methanol
is found to follow the rate equation
rate = kr[(CH3)3C—Cl]
a. What is the kinetic order with respect to tert-butyl chloride?
Verified step by step guidance1
Step 1: Analyze the given reaction. The reaction involves tert-butyl chloride ((CH3)3C—Cl) reacting with methanol (CH3—OH) to form methyl tert-butyl ether ((CH3)3C—OCH3) and HCl. This is a substitution reaction.
Step 2: Examine the rate equation provided: rate = Kt[(CH3)3C—Cl]. The rate equation indicates that the rate of the reaction depends only on the concentration of tert-butyl chloride.
Step 3: Recall the definition of kinetic order. The kinetic order with respect to a reactant is determined by the exponent of its concentration term in the rate equation. Here, the concentration of tert-butyl chloride is raised to the power of 1.
Step 4: Conclude that the reaction is first-order with respect to tert-butyl chloride because the rate equation shows a direct proportionality to [(CH3)3C—Cl] raised to the power of 1.
Step 5: Note that this reaction likely proceeds via an SN1 mechanism, as the rate depends only on the concentration of tert-butyl chloride and not on methanol. This mechanism involves the formation of a carbocation intermediate.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
1mWas this helpful?
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. The rate law expresses the relationship between the rate of a reaction and the concentration of its reactants. In this case, the rate equation indicates that the reaction rate depends only on the concentration of tert-butyl chloride, suggesting it is a first-order reaction with respect to this reactant.
Recommended video:
5:07
Rates of Intramolecular Reactions Concept 2
Substitution Reactions
The reaction of tert-butyl chloride with methanol is an example of a nucleophilic substitution reaction, where a nucleophile (methanol) replaces a leaving group (chloride ion). This type of reaction can proceed via different mechanisms, such as SN1 or SN2, with the SN1 mechanism being favored for tertiary alkyl halides like tert-butyl chloride due to steric hindrance.
Recommended video:
Guided course
01:34Recognizing Substitution Reactions.
Energy Diagrams
Energy diagrams visually represent the energy changes during a chemical reaction. They illustrate the transition states and intermediates, showing how the energy of the system changes from reactants to products. In this reaction, the energy diagram would depict the activation energy required for the formation of the carbocation intermediate, which is a key feature of the SN1 mechanism.
Recommended video:
Guided course
06:07Introduction to free energy diagrams.
Related Practice
Textbook Question
b. Calculate ΔH° for each step in this reaction.
c. Calculate the overall value of ΔH° for this reaction.
1
views
Textbook Question
The reaction of tert-butyl chloride with methanol
is found to follow the rate equation
rate = kr[(CH3)3C—Cl]
c. What is the kinetic order overall
2
views
Textbook Question
a. Using bond-dissociation enthalpies from Table 4-2. (page 167), calculate the heat of reaction for each step in the free-radical bromination of methane
b. Calculate the overall heat of the reaction.
Textbook Question
The reaction of tert-butyl chloride with methanol
is found to follow the rate equation
rate = kr[(CH3)3C—Cl]
b. What is the kinetic order with respect to methanol?
8
views
Textbook Question
Under certain conditions, the bromination of cyclohexene follows an unusual rate law:
a. What is the kinetic order with respect to cyclohexene?
2
views