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...
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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
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