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Determine the product(s) of the following substitution reaction: Br: HS DMSO

Determine the product(s) of the following substitution reaction: Br: HS DMSO

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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**Substitution Reaction Problem** Determine the product(s) of the following substitution reaction: **Reactants:** 1. A bromobutane (a butane chain with a bromine atom attached to the end carbon atom). 2. Benzene methanethiol (a thiol group attached to a benzene ring). **Conditions:** - The reaction takes place in Dimethyl sulfoxide (DMSO) indicated by the arrow pointing to "DMSO". In this reaction, the nucleophile from the benzene methanethiol (the thiol group, -SH) will perform a nucleophilic substitution on the bromobutane, replacing the bromine atom (Br) with the thiol group. The product(s) will be a thiol-functionalized butane: butane with a benzene methanethiol group attached to the end carbon atom where the bromine atom was originally located. This is typically a straightforward nucleophilic substitution reaction (S_N2), where the bromine atom leaves and is replaced by the thiol group. The solvent, DMSO, is a polar aprotic solvent which supports the S_N2 reaction mechanism. **Final Product Structure:** Butane-S-Benzenethiol (butane chain connected to a sulfur atom which is connected to a benzene ring). **Key Points:** - The thiol group (-SH) acts as a nucleophile. - The bromine atom (Br) is the leaving group. - The reaction occurs in DMSO, which is a polar aprotic solvent, favoring S_N2 reaction pathway.
Transcribed Image Text:**Substitution Reaction Problem** Determine the product(s) of the following substitution reaction: **Reactants:** 1. A bromobutane (a butane chain with a bromine atom attached to the end carbon atom). 2. Benzene methanethiol (a thiol group attached to a benzene ring). **Conditions:** - The reaction takes place in Dimethyl sulfoxide (DMSO) indicated by the arrow pointing to "DMSO". In this reaction, the nucleophile from the benzene methanethiol (the thiol group, -SH) will perform a nucleophilic substitution on the bromobutane, replacing the bromine atom (Br) with the thiol group. The product(s) will be a thiol-functionalized butane: butane with a benzene methanethiol group attached to the end carbon atom where the bromine atom was originally located. This is typically a straightforward nucleophilic substitution reaction (S_N2), where the bromine atom leaves and is replaced by the thiol group. The solvent, DMSO, is a polar aprotic solvent which supports the S_N2 reaction mechanism. **Final Product Structure:** Butane-S-Benzenethiol (butane chain connected to a sulfur atom which is connected to a benzene ring). **Key Points:** - The thiol group (-SH) acts as a nucleophile. - The bromine atom (Br) is the leaving group. - The reaction occurs in DMSO, which is a polar aprotic solvent, favoring S_N2 reaction pathway.
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