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.

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**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
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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