Textbook Question
Use the information in Table 4-2 (p. 167) to rank the following radicals in decreasing order of stability.
1
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 41d
Use bond-dissociation enthalpies (Table 4-2, p. 167) to calculate values of ΔH° for the following reactions.
d. CH3CH2CH3 + H2 → CH3CH3 + CH4
Verified step by step guidance1
Identify the bonds broken and formed in the reaction. In this case, the bonds broken are one C-H bond in CH3CH2CH3 (propane) and one H-H bond in H2. The bonds formed are one C-H bond in CH3CH3 (ethane) and one C-H bond in CH4 (methane).
Refer to the bond-dissociation enthalpy table (TABLE 4-2, p. 167) to find the bond-dissociation enthalpy values for each bond involved. For example, the bond-dissociation enthalpy for a C-H bond and an H-H bond will be listed in the table.
Calculate the total energy required to break the bonds. This is done by summing the bond-dissociation enthalpy values for the bonds broken (C-H in propane and H-H in H2).
Calculate the total energy released when the new bonds are formed. This is done by summing the bond-dissociation enthalpy values for the bonds formed (C-H in ethane and C-H in methane).
Determine the overall enthalpy change (ΔH°) for the reaction by subtracting the total energy released (bonds formed) from the total energy required (bonds broken). Use the formula: ΔH° = Σ(bonds broken) - Σ(bonds formed).
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
5mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Bond-Dissociation Enthalpy
Bond-dissociation enthalpy (BDE) is the energy required to break a specific bond in a molecule, resulting in the formation of free radicals. It is a crucial concept in thermochemistry, as it helps predict the stability of molecules and the energy changes during chemical reactions. BDE values are typically expressed in kilojoules per mole (kJ/mol) and vary depending on the type of bond and the molecular environment.
Recommended video:
Guided course
04:09
How to calculate enthalpy using bond dissociation energies.
Enthalpy Change (ΔH°)
The enthalpy change (ΔH°) of a reaction is the difference in enthalpy between the products and reactants under standard conditions. It indicates whether a reaction is exothermic (releases heat, ΔH° < 0) or endothermic (absorbs heat, ΔH° > 0). Calculating ΔH° using bond-dissociation enthalpies involves summing the BDEs of bonds broken in the reactants and subtracting the BDEs of bonds formed in the products.
Recommended video:
Guided course
04:38Calculating Enthalpies
Reaction Mechanism
A reaction mechanism describes the step-by-step sequence of elementary reactions by which overall chemical change occurs. Understanding the mechanism is essential for predicting the products and energy changes in a reaction. In the context of the given reaction, recognizing the bonds involved and their respective BDEs allows for accurate calculation of the overall enthalpy change, reflecting the energy dynamics of the process.
Recommended video:
Guided course
02:16Heck Reaction Mechanism
Related Practice
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
2
views
Textbook Question
Use bond-dissociation enthalpies (Table 4-2, p. 167) to calculate values of ΔH° for the following reactions.
c. (CH3)3C—OH + HCl → (CH3)3C—Cl + H2O
1
views
Textbook Question
For each alkane, which monobrominated derivatives could you form in good yield by free-radical bromination?
a. Cyclopentane
b. Methylcyclopentnae
6
views
Textbook Question
For each alkane,
2. determine whether free-radical chlorination would be a good way to make any of these monochlorinated derivatives. Will the reaction give mostly one major product?
a. Cyclopentane
b. Methylcyclopentane
1
views
Textbook Question
Use bond-dissociation enthalpies (Table 4-2, p. 167) to calculate values of ΔH° for the following reactions.
b. CH3CH2Cl + HI → CH3CH2I + HCl
2
views