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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![### Chemical Reaction Mechanism Exercise
#### Reaction Overview:
This educational exercise involves predicting the product and providing a stepwise detailed mechanism for the reaction sequence given. We will predict the product for the reaction of 2-bromo-1-methylcyclohexanol with sodium hydroxide (NaOH), followed by addition of methyl magnesium bromide (CH₃MgBr) and finally, water (H₂O).
#### Substance and Reaction Steps:
1. **Starting Material:**
- **2-bromo-1-methylcyclohexanol**
2. **Reagents:**
- **1) NaOH**
- **2) CH₃MgBr**
- **3) H₂O**
#### Detailed Steps:
1. **First Step: Reaction with NaOH**
- NaOH is a strong base and will deprotonate the hydroxyl group (-OH) on the cyclohexane ring, forming an alkoxide ion.
2. **Second Step: Addition of CH₃MgBr (Grignard Reagent)**
- The alkoxide ion will react with the methyl magnesium bromide (CH₃MgBr), adding a methyl group to the carbon bearing the bromine atom, resulting in the formation of a new C-C bond.
3. **Final Step: Addition of Water (H₂O)**
- The addition of water will protonate the alkoxide, converting it back to an alcohol, leading to the formation of the final product.
#### Stereochemical Outcome Prediction:
- It is crucial to carefully consider the stereochemical outcome of the reaction. During the mechanism, keep in mind the retention or inversion of configuration at stereocenters, as well as potential formations of racemic mixtures if applicable.
#### Explanation of Structures and Intermediate Steps:
- The starting material, 2-bromo-1-methylcyclohexanol, is shown with its hydroxyl and bromine substituents on a cyclohexane ring.
- The intermediate steps should display all formed intermediates with proper arrow pushing to show electron movement.
- The final product should display proper stereochemistry, indicating whether the configuration is retained or inverted.
By working through these steps systematically and carefully, the detailed mechanism and predicted product can be thoroughly understood and illustrated.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fb5f6837c-d2c0-4b1e-b9cf-8d2a3dea38c6%2F6f03a1b5-0b84-42cb-8b55-50d3122ef02e%2Fjdfyg3.png&w=3840&q=75)
Transcribed Image Text:### Chemical Reaction Mechanism Exercise
#### Reaction Overview:
This educational exercise involves predicting the product and providing a stepwise detailed mechanism for the reaction sequence given. We will predict the product for the reaction of 2-bromo-1-methylcyclohexanol with sodium hydroxide (NaOH), followed by addition of methyl magnesium bromide (CH₃MgBr) and finally, water (H₂O).
#### Substance and Reaction Steps:
1. **Starting Material:**
- **2-bromo-1-methylcyclohexanol**
2. **Reagents:**
- **1) NaOH**
- **2) CH₃MgBr**
- **3) H₂O**
#### Detailed Steps:
1. **First Step: Reaction with NaOH**
- NaOH is a strong base and will deprotonate the hydroxyl group (-OH) on the cyclohexane ring, forming an alkoxide ion.
2. **Second Step: Addition of CH₃MgBr (Grignard Reagent)**
- The alkoxide ion will react with the methyl magnesium bromide (CH₃MgBr), adding a methyl group to the carbon bearing the bromine atom, resulting in the formation of a new C-C bond.
3. **Final Step: Addition of Water (H₂O)**
- The addition of water will protonate the alkoxide, converting it back to an alcohol, leading to the formation of the final product.
#### Stereochemical Outcome Prediction:
- It is crucial to carefully consider the stereochemical outcome of the reaction. During the mechanism, keep in mind the retention or inversion of configuration at stereocenters, as well as potential formations of racemic mixtures if applicable.
#### Explanation of Structures and Intermediate Steps:
- The starting material, 2-bromo-1-methylcyclohexanol, is shown with its hydroxyl and bromine substituents on a cyclohexane ring.
- The intermediate steps should display all formed intermediates with proper arrow pushing to show electron movement.
- The final product should display proper stereochemistry, indicating whether the configuration is retained or inverted.
By working through these steps systematically and carefully, the detailed mechanism and predicted product can be thoroughly understood and illustrated.
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