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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Transcribed Image Text:### Chemistry Reaction Problem
**Problem:**
12. Give the product of the following reaction
**Diagram:**
- **Reactant:** A benzene ring with two substituents:
- A bromomethyl (CH2Br) group attached to one carbon atom.
- A bromine (Br) atom attached to a carbon adjacent to the bromomethyl group.
- **Reagent:** NaSH (sodium hydrosulfide).
The skeletal structure of the reactant indicates that it is 1-bromo-2-(bromomethyl)benzene. The directed arrow indicates that the reaction proceeds with NaSH.
**Explanation of Reaction:**
In this reaction, sodium hydrosulfide (NaSH) acts as a nucleophile. It is likely to participate in a nucleophilic substitution reaction (S_N2 type) with the bromomethyl group, resulting in the substitution of the bromine atom by a thiol (–SH) group.
**Expected Product:**
The product is expected to be 2-bromobenzyl thiol (1-bromo-2-(thiomethyl)benzene), where the bromomethyl group (–CH2Br) is replaced by a thiomethyl group (–CH2SH), while the bromine atom on the benzene ring remains intact.
So the product's structure will be:
- A benzene ring with:
- A thiomethyl (CH2SH) group attached to one carbon atom.
- A bromine (Br) atom attached to a carbon adjacent to the thiomethyl group.
This can be abbreviated as 1-bromo-2-(thiomethyl)benzene.
This transformation highlights a common method for introducing a thiol group into an organic molecule using NaSH as a nucleophile.
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