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1. Predict the product(s) and show the mechanism for each reaction below II. After finding the product, find how many C are there for each product and how many H signals in what integral ratio OTos CH3ONa CH3OH

1. Predict the product(s) and show the mechanism for each reaction below II. After finding the product, find how many C are there for each product and how many H signals in what integral ratio OTos CH3ONa CH3OH

Chemistry
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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**Title: Understanding Organic Reactions and Predicting Products** **I. Reaction Prediction and Mechanism Explanation** *Reactants:* - Starting material: A tertiary alkyl tosylate (OTos) - Reagents: Sodium methoxide (CH₃ONa) and methanol (CH₃OH) *Task:* Predict the products of the reaction between a tertiary alkyl tosylate and sodium methoxide in methanol. Illustrate the mechanism. *Reaction Overview:* - The structure depicted features a tertiary carbon bonded to an OTs group. In the presence of CH₃ONa and CH₃OH, an elimination reaction is likely due to the sterically hindered tertiary carbon. *Detailed Mechanism:* 1. **Deprotonation:** Sodium methoxide acts as a strong base, abstracting a proton from a β-hydrogen, leading to the formation of an alkene. 2. **Elimination:** The leaving group (OTs) departs, facilitating a bimolecular elimination (E2) reaction. *Expected Product:* - The likely outcome is an alkene formed by the elimination of the tosylate group, resulting in the release of tosylate ion (OTs⁻). **II. Analysis of Product – Carbon and Hydrogen Signals** *Carbon Count:* - Count the total number of carbons present in the product structure. *Hydrogen NMR Signals:* - Determine the integral ratio of hydrogen signals in the NMR spectrum of the product, indicating the different hydrogen environments. By understanding these fundamentals, one can predict reaction outcomes and analyze products using spectroscopy techniques effectively.
Transcribed Image Text:**Title: Understanding Organic Reactions and Predicting Products** **I. Reaction Prediction and Mechanism Explanation** *Reactants:* - Starting material: A tertiary alkyl tosylate (OTos) - Reagents: Sodium methoxide (CH₃ONa) and methanol (CH₃OH) *Task:* Predict the products of the reaction between a tertiary alkyl tosylate and sodium methoxide in methanol. Illustrate the mechanism. *Reaction Overview:* - The structure depicted features a tertiary carbon bonded to an OTs group. In the presence of CH₃ONa and CH₃OH, an elimination reaction is likely due to the sterically hindered tertiary carbon. *Detailed Mechanism:* 1. **Deprotonation:** Sodium methoxide acts as a strong base, abstracting a proton from a β-hydrogen, leading to the formation of an alkene. 2. **Elimination:** The leaving group (OTs) departs, facilitating a bimolecular elimination (E2) reaction. *Expected Product:* - The likely outcome is an alkene formed by the elimination of the tosylate group, resulting in the release of tosylate ion (OTs⁻). **II. Analysis of Product – Carbon and Hydrogen Signals** *Carbon Count:* - Count the total number of carbons present in the product structure. *Hydrogen NMR Signals:* - Determine the integral ratio of hydrogen signals in the NMR spectrum of the product, indicating the different hydrogen environments. By understanding these fundamentals, one can predict reaction outcomes and analyze products using spectroscopy techniques effectively.
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