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6. Draw a detailed arrow pushing mechanism for the following transformations: srl NaOCH3 SN2 Br + OCH3 18

6. Draw a detailed arrow pushing mechanism for the following transformations: srl NaOCH3 SN2 Br + OCH3 18

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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**Educational Website Content: Arrow Pushing Mechanisms** **Title: Understanding Arrow Pushing Mechanisms in Organic Chemistry** **Introduction:** In organic chemistry, understanding the mechanisms of reactions is crucial. Here, we explore two reaction mechanisms involving nucleophilic substitution: SN2 and SN1. These reactions involve changes in molecular structure and are represented through the technique of arrow pushing. **1. SN2 Reaction Mechanism:** **Reaction:** An alkyl bromide reacts with sodium methoxide (NaOCH₃) to form an ether. **Reactants:** - Alkyl bromide (structure shown with a bromine atom bonded to a carbon chain) - Sodium methoxide (NaOCH₃) **Product:** - Ether (the bromine is replaced by an OCH₃ group) **Process:** - This is a bimolecular nucleophilic substitution (SN2) where the nucleophile (CH₃O⁻) attacks the carbon atom bonded to bromine. - The reaction proceeds with a single concerted step, leading to the removal of the bromine atom and the formation of a new bond between the carbon and the methoxy group. **2. SN1 Reaction Mechanism:** **Reaction:** A cyclohexyl bromide reacts with an alcohol to form an ether. **Reactants:** - Cyclohexyl bromide (structure includes bromine attached to a cyclohexane ring) - Alcohol (secondary alcohol shown with an OH group) **Product:** - Ether (the bromine is replaced by an ether linkage involving the alcohol group) **Process:** - This is a unimolecular nucleophilic substitution (SN1). - The reaction involves the formation of a carbocation intermediate after the bromine leaves the molecule. - The alcohol acts as the nucleophile, attacking the carbocation to form the ether product. **Conclusion:** In these types of reactions, arrow pushing is utilized to illustrate electron movement during bond formation and breakage. Understanding these mechanisms allows chemists to predict the behavior of molecules during chemical transformations.
Transcribed Image Text:**Educational Website Content: Arrow Pushing Mechanisms** **Title: Understanding Arrow Pushing Mechanisms in Organic Chemistry** **Introduction:** In organic chemistry, understanding the mechanisms of reactions is crucial. Here, we explore two reaction mechanisms involving nucleophilic substitution: SN2 and SN1. These reactions involve changes in molecular structure and are represented through the technique of arrow pushing. **1. SN2 Reaction Mechanism:** **Reaction:** An alkyl bromide reacts with sodium methoxide (NaOCH₃) to form an ether. **Reactants:** - Alkyl bromide (structure shown with a bromine atom bonded to a carbon chain) - Sodium methoxide (NaOCH₃) **Product:** - Ether (the bromine is replaced by an OCH₃ group) **Process:** - This is a bimolecular nucleophilic substitution (SN2) where the nucleophile (CH₃O⁻) attacks the carbon atom bonded to bromine. - The reaction proceeds with a single concerted step, leading to the removal of the bromine atom and the formation of a new bond between the carbon and the methoxy group. **2. SN1 Reaction Mechanism:** **Reaction:** A cyclohexyl bromide reacts with an alcohol to form an ether. **Reactants:** - Cyclohexyl bromide (structure includes bromine attached to a cyclohexane ring) - Alcohol (secondary alcohol shown with an OH group) **Product:** - Ether (the bromine is replaced by an ether linkage involving the alcohol group) **Process:** - This is a unimolecular nucleophilic substitution (SN1). - The reaction involves the formation of a carbocation intermediate after the bromine leaves the molecule. - The alcohol acts as the nucleophile, attacking the carbocation to form the ether product. **Conclusion:** In these types of reactions, arrow pushing is utilized to illustrate electron movement during bond formation and breakage. Understanding these mechanisms allows chemists to predict the behavior of molecules during chemical transformations.
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