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.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Febef2a95-d468-4be7-b2f1-95e4c16dc461%2Fa0e8e0f1-5500-49d2-9c0f-77101bfc4cf0%2Fv4ryrkk_processed.jpeg&w=3840&q=75)
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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