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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![**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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Febef2a95-d468-4be7-b2f1-95e4c16dc461%2Fa722d32c-56cf-4160-b2fa-61549f73bf44%2Fmfojys9_processed.jpeg&w=3840&q=75)
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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