In the molecule shown below, determine which of the highlighted C-H bonds (from a to e) is expected to have the lowest bond dissociation energy. Ho C-Ha C-Hb C-Hc C-Hd C-He
In the molecule shown below, determine which of the highlighted C-H bonds (from a to e) is expected to have the lowest bond dissociation energy. Ho C-Ha C-Hb C-Hc C-Hd C-He
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
Related questions
Question
### Options:
A. \( \text{C-H}_a \)
B. \( \text{C-H}_b \)
C. \( \text{C-H}_c \)
D. \( \text{C-H}_d \)
E. \( \text{C-H}_e \)
### Analysis of the Molecule:
The given molecular structure includes several highlighted hydrogen atoms labeled \( \text{H}_a \), \( \text{H}_b \), \( \text{H}_c \), \( \text{H}_d \), and \( \text{H}_e \), which are bonded to respective carbon atoms in the cyclohexane ring, and one substituent.
### Determining Bond Dissociation Energy:
Bond dissociation energy (BDE) refers to the energy required to break a specific bond in a molecule homolytically, resulting in two radicals. Typically, factors such as bond strength, bond length, and the stability of the resulting radicals influence the dissociation energy. The actual analysis involves considering the type and environment of each C-H bond:
1. **Hyperconjugation**: Bonds adjacent to a more significant number of hydrogen atoms often show lower BDE due to hyperconjugation effects.
2. **Inductive effects**: Electronegative substituents might affect nearby C-H bonds, altering the BDE.
3. **Radical stability**: The more stable the resulting radical, the lower the bond dissociation energy.
Using these principles, one can predict that the bond with the potentially lowest dissociation energy would be the one adjacent to more stabilizing interactions (like hyperconjugation or inductive effects) or forming the most stable free radical on dissociation.
For detailed reasoning and final answer derivation, evaluating the specific electronic and structural environment of each C-H bond in the context of the molecule's geometry and substituent effects is crucial.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fec41627d-7715-46d4-accb-fe042454172c%2Fb55bb82c-1651-4745-bdfc-b3cba6b0f9a8%2Fzwjm45_processed.jpeg&w=3840&q=75)
Transcribed Image Text:### Bond Dissociation Energy Analysis
In the molecule shown below, determine which of the highlighted C-H bonds (from a to e) is expected to have the lowest bond dissociation energy.
### Options:
A. \( \text{C-H}_a \)
B. \( \text{C-H}_b \)
C. \( \text{C-H}_c \)
D. \( \text{C-H}_d \)
E. \( \text{C-H}_e \)
### Analysis of the Molecule:
The given molecular structure includes several highlighted hydrogen atoms labeled \( \text{H}_a \), \( \text{H}_b \), \( \text{H}_c \), \( \text{H}_d \), and \( \text{H}_e \), which are bonded to respective carbon atoms in the cyclohexane ring, and one substituent.
### Determining Bond Dissociation Energy:
Bond dissociation energy (BDE) refers to the energy required to break a specific bond in a molecule homolytically, resulting in two radicals. Typically, factors such as bond strength, bond length, and the stability of the resulting radicals influence the dissociation energy. The actual analysis involves considering the type and environment of each C-H bond:
1. **Hyperconjugation**: Bonds adjacent to a more significant number of hydrogen atoms often show lower BDE due to hyperconjugation effects.
2. **Inductive effects**: Electronegative substituents might affect nearby C-H bonds, altering the BDE.
3. **Radical stability**: The more stable the resulting radical, the lower the bond dissociation energy.
Using these principles, one can predict that the bond with the potentially lowest dissociation energy would be the one adjacent to more stabilizing interactions (like hyperconjugation or inductive effects) or forming the most stable free radical on dissociation.
For detailed reasoning and final answer derivation, evaluating the specific electronic and structural environment of each C-H bond in the context of the molecule's geometry and substituent effects is crucial.
Expert Solution
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 4 steps with 1 images
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Recommended textbooks for you
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY