Textbook Question
Using the given starting material and any necessary organic or inorganic reagents, indicate how the desired compounds could be synthesized:
a.
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Ch. 12 - Radicals
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
Chapter 13, Problem 41b
Given that ∆H° for the reaction is -42 kcal/mol and the bond dissociation enthalpies for the C−H, C−Cl, and O−H bonds are 101, 85, and 105 kcal/mol respectively, calculate the bond dissociation enthalpy of the O−Cl bond.
Verified step by step guidance1
Step 1: Analyze the reaction provided in the image. The reactants are tert-butyl hypochlorite (C4H9OCl) and isobutane (C4H10), and the products are tert-butyl alcohol (C4H9OH) and tert-butyl chloride (C4H9Cl). This reaction involves bond dissociation and formation.
Step 2: Write the bond dissociation and formation processes. Bonds broken: C−H (from isobutane), O−Cl (from tert-butyl hypochlorite). Bonds formed: O−H (in tert-butyl alcohol), C−Cl (in tert-butyl chloride).
Step 3: Use the enthalpy change formula for the reaction: ∆H° = Σ(Bonds broken) − Σ(Bonds formed). Substitute the given values: ∆H° = -42 kcal/mol, bond dissociation enthalpies for C−H = 101 kcal/mol, C−Cl = 85 kcal/mol, O−H = 105 kcal/mol.
Step 4: Rearrange the formula to solve for the bond dissociation enthalpy of O−Cl. Let the bond dissociation enthalpy of O−Cl be x. The equation becomes: -42 = (101 + x) − (85 + 105).
Step 5: Simplify the equation to isolate x. Perform algebraic manipulation to calculate the bond dissociation enthalpy of O−Cl.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Bond Dissociation Enthalpy (BDE)
Bond dissociation enthalpy is the energy required to break a specific bond in a molecule, resulting in the formation of free radicals. It is typically expressed in kcal/mol and reflects the strength of the bond; higher values indicate stronger bonds. Understanding BDE is crucial for predicting reaction pathways and the stability of intermediates in organic reactions.
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How to calculate enthalpy using bond dissociation energies.
Enthalpy Change (∆H°)
Enthalpy change (∆H°) is the heat content change associated with a chemical reaction at constant pressure. A negative ∆H° indicates that the reaction is exothermic, releasing energy, while a positive ∆H° signifies an endothermic reaction, absorbing energy. This concept is essential for calculating the overall energy changes in reactions, including bond formation and breaking.
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Reaction Mechanism
A reaction mechanism describes the step-by-step sequence of elementary reactions by which overall chemical change occurs. It provides insight into how reactants are converted into products, including the formation and breaking of bonds. Understanding the mechanism is vital for predicting the products of a reaction and calculating the associated energy changes, such as bond dissociation enthalpies.
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Related Practice
Textbook Question
Starting with cyclohexane, how could the following compounds be prepared?
e.
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Textbook Question
Using the given starting material and any necessary organic or inorganic reagents, indicate how the desired compounds could be synthesized:
c.
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Textbook Question
Starting with cyclohexane, how could the following compounds be prepared?
c.
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Textbook Question
A chemist wanted to determine experimentally the relative ease of removing a hydrogen atom from a tertiary, a secondary, and a primary carbon by a chlorine radical. He allowed 2-methylbutane to undergo chlorination at 300 °C and obtained as products 36% 1-chloro-2-methylbutane, 18% 2-chloro-2-methylbutane, 28% 2-chloro-3-methylbutane, and 18% 1-chloro-3-methylbutane. What values did he obtain for the relative ease of removing a hydrogen atom from tertiary, secondary, and primary hydrogen carbons by a chlorine radical under the conditions of his experiment?
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Textbook Question
Propose a mechanism for the following reaction:
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