Draw a valence-bond (balloon-animal) orbital picture of an ethyl cation. With reference to your awing, explain how hyperconjugative stabilization works. Also, next to the Lewis structure below, draw ne "no-bond" resonance contributing structure that represents hyperconjugative stabilization of the tion.

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...
icon
Related questions
icon
Concept explainers
Question
### Hyperconjugative Stabilization in Ethyl Cation: An Educational Illustration

**Question 7:** Draw a valence-bond (balloon-animal) orbital picture of an ethyl cation. With reference to your drawing, explain how hyperconjugative stabilization works. Also, next to the Lewis structure below, draw one "no-bond" resonance contributing structure that represents hyperconjugative stabilization of the cation.

**Lewis Structure:**

The given Lewis structure for the ethyl cation is:

```
         H
         |
H ─ C ─ C^+
    |   |
    H   H
```

**Explanation of Hyperconjugative Stabilization:**

Hyperconjugation is a stabilizing interaction that results from the delocalization of electrons in sigma bonds (C-H or C-C) to an adjacent empty or partially filled non-bonding p-orbital or antibonding σ* orbital. In the case of the ethyl cation, the positive charge on the carbon (C+) adjacent to one or more C-H bonds allows for hyperconjugative interactions. This delocalization serves to stabilize the positive charge on the carbon atom.

### Orbital Picture and Explanation:

**Valence-Bond Description:**

- The ethyl cation (C2H5+) consists of two carbon atoms: one bearing a positive charge (C+) and the other bonded to three hydrogen atoms (CH3).
- The positively charged carbon has no electrons in its p-orbital, making it an empty orbital.
- The electrons in the adjacent C-H bonds can delocalize into this empty p-orbital, providing stabilization to the cation.

### "No-Bond" Resonance Structure:

To represent this hyperconjugative stabilization, we draw a resonance structure showing the delocalization. This "no-bond" resonance structure illustrates the shift of electron density:

```
   H      H
    |      |
H  —  C  == C  + 
    |      |
    H      H
```

In this diagram:

- The double-headed arrow indicates resonance or delocalization between the standard Lewis structure and the "no-bond" contributing structure.
- The double bond (==) signifies the delocalized electrons from the sigma C-H bonds into the empty p-orbital on the adjacent carbon atom carrying a positive charge.

### Summary:

In hyperconjugation,
Transcribed Image Text:### Hyperconjugative Stabilization in Ethyl Cation: An Educational Illustration **Question 7:** Draw a valence-bond (balloon-animal) orbital picture of an ethyl cation. With reference to your drawing, explain how hyperconjugative stabilization works. Also, next to the Lewis structure below, draw one "no-bond" resonance contributing structure that represents hyperconjugative stabilization of the cation. **Lewis Structure:** The given Lewis structure for the ethyl cation is: ``` H | H ─ C ─ C^+ | | H H ``` **Explanation of Hyperconjugative Stabilization:** Hyperconjugation is a stabilizing interaction that results from the delocalization of electrons in sigma bonds (C-H or C-C) to an adjacent empty or partially filled non-bonding p-orbital or antibonding σ* orbital. In the case of the ethyl cation, the positive charge on the carbon (C+) adjacent to one or more C-H bonds allows for hyperconjugative interactions. This delocalization serves to stabilize the positive charge on the carbon atom. ### Orbital Picture and Explanation: **Valence-Bond Description:** - The ethyl cation (C2H5+) consists of two carbon atoms: one bearing a positive charge (C+) and the other bonded to three hydrogen atoms (CH3). - The positively charged carbon has no electrons in its p-orbital, making it an empty orbital. - The electrons in the adjacent C-H bonds can delocalize into this empty p-orbital, providing stabilization to the cation. ### "No-Bond" Resonance Structure: To represent this hyperconjugative stabilization, we draw a resonance structure showing the delocalization. This "no-bond" resonance structure illustrates the shift of electron density: ``` H H | | H — C == C + | | H H ``` In this diagram: - The double-headed arrow indicates resonance or delocalization between the standard Lewis structure and the "no-bond" contributing structure. - The double bond (==) signifies the delocalized electrons from the sigma C-H bonds into the empty p-orbital on the adjacent carbon atom carrying a positive charge. ### Summary: In hyperconjugation,
Expert Solution
steps

Step by step

Solved in 5 steps with 5 images

Blurred answer
Knowledge Booster
Basics in Organic Reaction Mechanisms
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.
Similar questions
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY