What product would be obtained from the reaction of cyclopropane with `Cl_(2)` in the presence of `FeCl_(3)`?

Options

A. 1,2-dichloropropane
B. 1,2-dichlorocyclopropane
C. 1,3-dichloropropane
D. 1,1-dichlropropane

Answer

To determine the product obtained from the reaction of cyclopropane with Cl₂ in the presence of FeCl₃, we can follow these steps:

### Step-by-Step Solution:

1. **Identify the Reactants**:
- The reactants are cyclopropane (C₃H₆) and chlorine gas (Cl₂) in the presence of iron(III) chloride (FeCl₃).

2. **Understand the Role of FeCl₃**:
- FeCl₃ acts as a Lewis acid and helps generate a more reactive electrophile from Cl₂. It facilitates the formation of Cl⁺ (chloronium ion) and Cl⁻ (chloride ion) which can react with cyclopropane.

3. **Formation of Electrophile**:
- In the presence of FeCl₃, Cl₂ dissociates to form Cl⁺ and Cl⁻:
\[ \text{Cl}_2 + \text{FeCl}_3 \rightarrow \text{Cl}^+ + \text{FeCl}_4^- \]
- Here, Cl⁺ is the electrophile that will react with cyclopropane.

4. **Cyclopropane Structure**:
- Cyclopropane has a strained three-membered ring structure with sp³ hybridized carbons. The bond angles are approximately 60 degrees, which leads to significant ring strain.

5. **Electrophilic Attack**:
- The electrophile Cl⁺ attacks one of the carbon atoms in cyclopropane, leading to the opening of the ring. The C-C bond breaks due to the ring strain, resulting in a carbocation intermediate:
\[ \text{Cyclopropane} \xrightarrow{\text{Cl}^+} \text{CH}_2^+ - \text{CH}_2 - \text{CH}_2 \]

6. **Formation of the Product**:
- The Cl⁻ ion generated from the dissociation of Cl₂ can now attack the carbocation formed after the ring opening. The final product will be a chain of three carbon atoms (propane) with chlorine substituents:
\[ \text{CH}_2 - \text{CH} - \text{CH}_2 \text{ with Cl on both ends} \]

7. **Naming the Product**:
- The product has two chlorine atoms attached to the first and third carbon of the propane chain. Thus, the compound is named 1,3-dichloropropane.

### Final Answer:
The product obtained from the reaction of cyclopropane with Cl₂ in the presence of FeCl₃ is **1,3-dichloropropane**.

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