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:### Reaction Prediction Problem
**Question:**
Predict the product for the following reaction.
**Reaction Details:**
1. **Reactants:**
- A benzene ring with a propyl group (isopropylbenzene) attached.
- An acyl chloride (butanoyl chloride).
2. **Reagents:**
- Aluminum chloride (AlCl₃)
- Dimethylamine ((CH₃)₂NH)
- Sulfuric acid (H₂SO₄)
- Sodium cyanoborohydride (NaBH₃CN)
**Discussion:**
- The reaction begins with the use of AlCl₃, a catalyst for the Friedel-Crafts acylation. This will facilitate the addition of the acyl group from the acyl chloride to the benzene ring.
- The dimethylamine indicates the formation of an iminium ion intermediate. This will likely react through reductive amination, given the presence of NaBH₃CN, which is a reducing agent.
- The use of sulfuric acid suggests an acid-catalyzed step in the reaction mechanism, potentially related to the activation of the acyl chloride or amine.
Through these steps, the proposed mechanism includes:
- Formation of a ketone intermediate via Friedel-Crafts acylation.
- Reaction with dimethylamine to form an iminium ion.
- Reduction by sodium cyanoborohydride to yield a secondary amine as the final product.
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