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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![**Problem 7: Propose a Mechanism for the Following Reaction Favoring an SN1 Reaction**
The question involves predicting a mechanism for a chemical reaction under conditions that favor an SN1 reaction.
**Reactants and Products:**
- **Reactant:** A cyclopentane ring attached to a carbon chain with a bromine atom (\(Br\)) as a leaving group.
- **Solvent:** Water (\(H_2O\)).
- **Product:** A cyclopentane ring attached to a carbon chain with a hydroxyl group (\(OH\)).
**Reaction Details:**
1. **Formation of Carbocation:**
- The reaction begins with the departure of the bromine ion (\(Br^-\)), forming a carbocation. This step is crucial in an SN1 mechanism and involves the generation of an intermediate with a positive charge due to the loss of the leaving group.
2. **Nucleophilic Attack:**
- The water molecule, acting as a nucleophile, attacks the carbocation at the positively charged carbon, leading to the formation of an oxonium ion.
3. **Deprotonation:**
- Finally, the oxonium ion donates a proton (\(H^+\)) to the surrounding solvent, stabilizing the system and resulting in the formation of the alcohol (\(OH\)) as the final product.
**Notes on SN1 Mechanism:**
- An SN1 reaction involves a two-step mechanism characterized by the formation of a carbocation intermediate.
- These reactions are typically favored in polar protic solvents like water, which can stabilize the carbocation and the leaving group.
This illustrates a common transformation in organic chemistry where a halide group is replaced by a hydroxyl group under the influence of a polar protic solvent through an SN1 pathway.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F430bf55b-cd13-42e4-b9bc-47cb9df7ce37%2F5dd879e3-f2a3-4c42-b732-5f8883814dfb%2Ftkx884k_processed.png&w=3840&q=75)
Transcribed Image Text:**Problem 7: Propose a Mechanism for the Following Reaction Favoring an SN1 Reaction**
The question involves predicting a mechanism for a chemical reaction under conditions that favor an SN1 reaction.
**Reactants and Products:**
- **Reactant:** A cyclopentane ring attached to a carbon chain with a bromine atom (\(Br\)) as a leaving group.
- **Solvent:** Water (\(H_2O\)).
- **Product:** A cyclopentane ring attached to a carbon chain with a hydroxyl group (\(OH\)).
**Reaction Details:**
1. **Formation of Carbocation:**
- The reaction begins with the departure of the bromine ion (\(Br^-\)), forming a carbocation. This step is crucial in an SN1 mechanism and involves the generation of an intermediate with a positive charge due to the loss of the leaving group.
2. **Nucleophilic Attack:**
- The water molecule, acting as a nucleophile, attacks the carbocation at the positively charged carbon, leading to the formation of an oxonium ion.
3. **Deprotonation:**
- Finally, the oxonium ion donates a proton (\(H^+\)) to the surrounding solvent, stabilizing the system and resulting in the formation of the alcohol (\(OH\)) as the final product.
**Notes on SN1 Mechanism:**
- An SN1 reaction involves a two-step mechanism characterized by the formation of a carbocation intermediate.
- These reactions are typically favored in polar protic solvents like water, which can stabilize the carbocation and the leaving group.
This illustrates a common transformation in organic chemistry where a halide group is replaced by a hydroxyl group under the influence of a polar protic solvent through an SN1 pathway.
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