Consider the reaction below to answer the following questions. When dichlorocarbene is generated in the presence of an alkene, a dichlorocyclopropane is formed. Cl H₂C CH3 C=C + CHCl3 1 H H KOH H₂C CH3 H H Write the complete stepwise mechanism for the formation of dichlorocarbene, :CC1₂. Show all intermediate structures and show all electron flow with arrows.
Consider the reaction below to answer the following questions. When dichlorocarbene is generated in the presence of an alkene, a dichlorocyclopropane is formed. Cl H₂C CH3 C=C + CHCl3 1 H H KOH H₂C CH3 H H Write the complete stepwise mechanism for the formation of dichlorocarbene, :CC1₂. Show all intermediate structures and show all electron flow with arrows.
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
![**Understanding the Formation of Dichlorocyclopropane**
In this exercise, we'll explore the reaction in which dichlorocarbene is generated in the presence of an alkene, leading to the formation of dichlorocyclopropane.
**Reaction Overview:**
- **Reactants:** Propene (H₃C-CH=CH₂) and chloroform (CHCl₃)
- **Reagent:** KOH (Potassium hydroxide)
- **Product:** Dichlorocyclopropane
**Objective:**
To write and understand the complete stepwise mechanism for the formation of dichlorocarbene (:CCl₂). It’s crucial to display all intermediate structures and illustrate the electron flow using arrows.
### Stepwise Mechanism:
1. **Deprotonation of Chloroform:**
- Potassium hydroxide (KOH) acts as a base and deprotonates chloroform (CHCl₃) to form the trichloromethide ion (CCl₃⁻).
2. **Formation of Dichlorocarbene:**
- The trichloromethide ion (CCl₃⁻) undergoes elimination of a chloride ion (Cl⁻), forming dichlorocarbene (:CCl₂).
3. **Cyclopropanation of the Alkene:**
- Dichlorocarbene (:CCl₂) reacts with the alkene (H₃C-CH=CH₂) to form dichlorocyclopropane.
- The vacant p-orbital of :CCl₂ overlaps with the π-bond of the alkene, resulting in the formation of a three-membered ring.
### Diagram Explanation:
There is a structural illustration showing the initial reactants on the left: the alkene with one hydrogen and two carbon groups (H₃C-CH=CH₂) and chloroform (CHCl₃) with the presence of a KOH arrow pointing toward the product on the right, which is dichlorocyclopropane with two chlorine atoms incorporated at the points of a cyclopropane structure.
### Key Points:
- **Electron Flow:** Use arrows to indicate the movement from electron-rich species (base or nucleophile) to electron-deficient species (electrophile or carbene center).
- **Reaction Conditions:** Typically conducted under controlled conditions to](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F17240ec3-a1b6-433b-936a-3fd00ad8499d%2F530696b7-379b-4ccd-9082-b40b5b32bf2b%2Ffrysr1c_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Understanding the Formation of Dichlorocyclopropane**
In this exercise, we'll explore the reaction in which dichlorocarbene is generated in the presence of an alkene, leading to the formation of dichlorocyclopropane.
**Reaction Overview:**
- **Reactants:** Propene (H₃C-CH=CH₂) and chloroform (CHCl₃)
- **Reagent:** KOH (Potassium hydroxide)
- **Product:** Dichlorocyclopropane
**Objective:**
To write and understand the complete stepwise mechanism for the formation of dichlorocarbene (:CCl₂). It’s crucial to display all intermediate structures and illustrate the electron flow using arrows.
### Stepwise Mechanism:
1. **Deprotonation of Chloroform:**
- Potassium hydroxide (KOH) acts as a base and deprotonates chloroform (CHCl₃) to form the trichloromethide ion (CCl₃⁻).
2. **Formation of Dichlorocarbene:**
- The trichloromethide ion (CCl₃⁻) undergoes elimination of a chloride ion (Cl⁻), forming dichlorocarbene (:CCl₂).
3. **Cyclopropanation of the Alkene:**
- Dichlorocarbene (:CCl₂) reacts with the alkene (H₃C-CH=CH₂) to form dichlorocyclopropane.
- The vacant p-orbital of :CCl₂ overlaps with the π-bond of the alkene, resulting in the formation of a three-membered ring.
### Diagram Explanation:
There is a structural illustration showing the initial reactants on the left: the alkene with one hydrogen and two carbon groups (H₃C-CH=CH₂) and chloroform (CHCl₃) with the presence of a KOH arrow pointing toward the product on the right, which is dichlorocyclopropane with two chlorine atoms incorporated at the points of a cyclopropane structure.
### Key Points:
- **Electron Flow:** Use arrows to indicate the movement from electron-rich species (base or nucleophile) to electron-deficient species (electrophile or carbene center).
- **Reaction Conditions:** Typically conducted under controlled conditions to
Expert Solution
![](/static/compass_v2/shared-icons/check-mark.png)
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
Step by step
Solved in 2 steps with 2 images
![Blurred answer](/static/compass_v2/solution-images/blurred-answer.jpg)
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](https://www.bartleby.com/isbn_cover_images/9781305957404/9781305957404_smallCoverImage.gif)
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781259911156/9781259911156_smallCoverImage.gif)
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
![Principles of Instrumental Analysis](https://www.bartleby.com/isbn_cover_images/9781305577213/9781305577213_smallCoverImage.gif)
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781305957404/9781305957404_smallCoverImage.gif)
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781259911156/9781259911156_smallCoverImage.gif)
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
![Principles of Instrumental Analysis](https://www.bartleby.com/isbn_cover_images/9781305577213/9781305577213_smallCoverImage.gif)
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
![Organic Chemistry](https://www.bartleby.com/isbn_cover_images/9780078021558/9780078021558_smallCoverImage.gif)
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
![Chemistry: Principles and Reactions](https://www.bartleby.com/isbn_cover_images/9781305079373/9781305079373_smallCoverImage.gif)
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
![Elementary Principles of Chemical Processes, Bind…](https://www.bartleby.com/isbn_cover_images/9781118431221/9781118431221_smallCoverImage.gif)
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY