Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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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.
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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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