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...
Related questions
Question
![**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
Expert Solution

This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 2 steps with 1 images

Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Recommended textbooks for you

Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning

Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education

Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning

Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY