Determine the product(s) of the following substitution reaction: NaCN DMF :3:

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**Determine the Product(s) of the Following Substitution Reaction:**

The image shows a chemical reaction where a 5-membered cyclopentane ring is substituted with a chlorine atom (Cl) and a methyl group (CH3). The chlorine atom is substituted at the 1-position (highlighted in bold), and the methyl group is located on the adjacent carbon (at the 2-position with a wedged bond indicating it's in the up position).

The reagents provided for this reaction are sodium cyanide (NaCN) and dimethylformamide (DMF). Here's how the reaction proceeds:

1. **Reagent Interaction**: Sodium cyanide (NaCN) often acts as a nucleophile in a substitution reaction. DMF (dimethylformamide) is commonly used as a polar aprotic solvent which facilitates such substitution reactions.

2. **Reaction Mechanism**:
   - **Formation of Cyanide Ion (CN⁻)**: In the presence of DMF, NaCN dissociates to produce free cyanide ions (CN⁻) which are strong nucleophiles.
   - **Nucleophilic Substitution**: The cyanide ion (CN⁻) attacks the carbon bearing the chlorine atom (which is a good leaving group). This leads to the substitution of chlorine by the cyanide ion.

3. **Resultant Product**:
   - The product of this nucleophilic substitution reaction is 1-Cyanocyclopentane.

**Reaction Equation**:
   \[
   \ce{Cyclopentane-1-Chloride + NaCN ->[DMF] Cyclopentane-1-Cyanide + NaCl}
   \]

**Detailed Steps of the Mechanism**:
- Step 1: The carbon-chlorine (C-Cl) bond in the cyclopentyl chloride is polarized, with a partial positive charge on carbon and a partial negative charge on chlorine due to the electronegativity of chlorine.
- Step 2: The nucleophilic cyanide ion (CN⁻) attacks the electrophilic carbon (which attached to Cl), resulting in the expulsion of the chloride ion (Cl⁻).
- Step 3: The product formed is cyclopentyl cyanide, where the cyanide group has replaced the chlorine atom.

This reaction demonstrates a typical SN2 (bimolecular nucleophilic substitution) mechanism, which is common for these types of substrates under
Transcribed Image Text:**Determine the Product(s) of the Following Substitution Reaction:** The image shows a chemical reaction where a 5-membered cyclopentane ring is substituted with a chlorine atom (Cl) and a methyl group (CH3). The chlorine atom is substituted at the 1-position (highlighted in bold), and the methyl group is located on the adjacent carbon (at the 2-position with a wedged bond indicating it's in the up position). The reagents provided for this reaction are sodium cyanide (NaCN) and dimethylformamide (DMF). Here's how the reaction proceeds: 1. **Reagent Interaction**: Sodium cyanide (NaCN) often acts as a nucleophile in a substitution reaction. DMF (dimethylformamide) is commonly used as a polar aprotic solvent which facilitates such substitution reactions. 2. **Reaction Mechanism**: - **Formation of Cyanide Ion (CN⁻)**: In the presence of DMF, NaCN dissociates to produce free cyanide ions (CN⁻) which are strong nucleophiles. - **Nucleophilic Substitution**: The cyanide ion (CN⁻) attacks the carbon bearing the chlorine atom (which is a good leaving group). This leads to the substitution of chlorine by the cyanide ion. 3. **Resultant Product**: - The product of this nucleophilic substitution reaction is 1-Cyanocyclopentane. **Reaction Equation**: \[ \ce{Cyclopentane-1-Chloride + NaCN ->[DMF] Cyclopentane-1-Cyanide + NaCl} \] **Detailed Steps of the Mechanism**: - Step 1: The carbon-chlorine (C-Cl) bond in the cyclopentyl chloride is polarized, with a partial positive charge on carbon and a partial negative charge on chlorine due to the electronegativity of chlorine. - Step 2: The nucleophilic cyanide ion (CN⁻) attacks the electrophilic carbon (which attached to Cl), resulting in the expulsion of the chloride ion (Cl⁻). - Step 3: The product formed is cyclopentyl cyanide, where the cyanide group has replaced the chlorine atom. This reaction demonstrates a typical SN2 (bimolecular nucleophilic substitution) mechanism, which is common for these types of substrates under
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