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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Question
Predict the major products of each reaction and its stereochemistry. Write NR if none found.
![### Chemical Reactions: Stereochemistry and Reaction Mechanisms
#### Reaction 8
![Chemical Structure]
**Substrate**: 1-chloro-2-methylpropane (CH₃CHClD)
**Reagent**: Sodium methoxide (CH₃ONa)
**Reaction**: The substrate undergoes a reaction with sodium methoxide.
#### Reaction 9
![Chemical Structure]
**Substrate**: Bromo-cyclohexane
**Reagent**: Water (H₂O)
**Reaction**: The substrate undergoes a reaction with water.
---
### Detailed Explanations
#### Reaction 8:
This is an example of an S_N2 (bimolecular nucleophilic substitution) reaction. Sodium methoxide (CH₃ONa) acts as a strong nucleophile. It attacks the carbon attached to the chlorine, displacing the chlorine atom due to the backside attack mechanism typical in S_N2 reactions. Given that the chlorine is attached to a chiral center, this attack results in inversion of configuration at that carbon center.
#### Reaction 9:
This reaction typically follows an S_N1 (unimolecular nucleophilic substitution) mechanism. Here, the substrate bromo-cyclohexane first undergoes ionization to form a carbocation intermediate with the loss of a bromide ion (Br⁻). Water (H₂O) acts as a nucleophile and attacks the carbocation, leading to the formation of a substituted cyclohexane.
For further reactions and detailed mechanisms, always consider the specific conditions and reactivity patterns of the reagents used.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F8c772ec7-1ff1-499d-9ec1-b5ffac417bc5%2F7bab618c-617b-423b-9410-674f38194d4b%2Fhaj311vj.jpeg&w=3840&q=75)
Transcribed Image Text:### Chemical Reactions: Stereochemistry and Reaction Mechanisms
#### Reaction 8
![Chemical Structure]
**Substrate**: 1-chloro-2-methylpropane (CH₃CHClD)
**Reagent**: Sodium methoxide (CH₃ONa)
**Reaction**: The substrate undergoes a reaction with sodium methoxide.
#### Reaction 9
![Chemical Structure]
**Substrate**: Bromo-cyclohexane
**Reagent**: Water (H₂O)
**Reaction**: The substrate undergoes a reaction with water.
---
### Detailed Explanations
#### Reaction 8:
This is an example of an S_N2 (bimolecular nucleophilic substitution) reaction. Sodium methoxide (CH₃ONa) acts as a strong nucleophile. It attacks the carbon attached to the chlorine, displacing the chlorine atom due to the backside attack mechanism typical in S_N2 reactions. Given that the chlorine is attached to a chiral center, this attack results in inversion of configuration at that carbon center.
#### Reaction 9:
This reaction typically follows an S_N1 (unimolecular nucleophilic substitution) mechanism. Here, the substrate bromo-cyclohexane first undergoes ionization to form a carbocation intermediate with the loss of a bromide ion (Br⁻). Water (H₂O) acts as a nucleophile and attacks the carbocation, leading to the formation of a substituted cyclohexane.
For further reactions and detailed mechanisms, always consider the specific conditions and reactivity patterns of the reagents used.
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