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:### Topic: Likely Inhibited Reaction in Organic Chemistry
#### Question:
**Explain in a sentence or two why the following reaction is not likely to occur.**
#### Reaction Diagram:
- **Reactant:** A benzene ring with a nitro group (NO₂) attached at the top (para position) and a methyl group (CH₃) to be potentially added at the opposite para position.
- **Reagents:**
- Methyl Chloride (CH₃Cl)
- Aluminum Chloride (AlCl₃)
### Analysis:
In the provided reaction diagram, the reactant is a nitrobenzene ring, which is proposed to undergo a Friedel-Crafts alkylation reaction using methyl chloride (CH₃Cl) and aluminum chloride (AlCl₃) as the catalyst.
### Explanation:
The reaction is not likely to occur because the nitro group (NO₂) attached to the benzene ring is a strong deactivating group. It withdraws electron density from the ring through both resonance and inductive effects, significantly reducing the electron density on the aromatic ring. Since Friedel-Crafts alkylation reactions require a nucleophilic aromatic ring, the electron-deficient nature of nitrobenzene makes it highly resistant to such electrophilic aromatic substitution reactions. As a result, the reaction is generally not successful.
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