Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Question
**Title: Predicting the Major Product of a Nucleophilic Substitution Reaction** **Question:** Draw the major product of the following reaction. **Reaction Details:** - **Reactant:** The initial compound is a brominated alkane with the configuration showing the bromine (Br) atom as a wedge, indicating its stereochemistry. - **Reagent:** The reagent is a negatively charged tert-butoxide ion, OC(CH₃)₃⁻. - **Reaction Arrow:** Indicates the progression from reactant to product. **Explanation:** In this reaction, we are dealing with a nucleophilic substitution, where the tert-butoxide ion acts as the nucleophile. Given the sterics and the strength of the base, the reaction is likely to proceed via an elimination mechanism (E2), rather than substitution, due to steric hindrance. This leads to the formation of an alkene. **Expected Major Product:** - The elimination will typically favor the more substituted alkene due to Zaitsev's rule, which predicts that the most stable alkene (usually the one with the more highly substituted double bond) will be the major product. **Conclusion:** Using this understanding, draw the expected alkene product, taking into account the stereochemistry and the most substituted possible product.
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Transcribed Image Text:**Title: Predicting the Major Product of a Nucleophilic Substitution Reaction** **Question:** Draw the major product of the following reaction. **Reaction Details:** - **Reactant:** The initial compound is a brominated alkane with the configuration showing the bromine (Br) atom as a wedge, indicating its stereochemistry. - **Reagent:** The reagent is a negatively charged tert-butoxide ion, OC(CH₃)₃⁻. - **Reaction Arrow:** Indicates the progression from reactant to product. **Explanation:** In this reaction, we are dealing with a nucleophilic substitution, where the tert-butoxide ion acts as the nucleophile. Given the sterics and the strength of the base, the reaction is likely to proceed via an elimination mechanism (E2), rather than substitution, due to steric hindrance. This leads to the formation of an alkene. **Expected Major Product:** - The elimination will typically favor the more substituted alkene due to Zaitsev's rule, which predicts that the most stable alkene (usually the one with the more highly substituted double bond) will be the major product. **Conclusion:** Using this understanding, draw the expected alkene product, taking into account the stereochemistry and the most substituted possible product.
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