10. Nitril group, -CN, is a meta director. Predict the product for the following reaction, by proposing a plausible mechanism. Make sure show resonance structures to explain selectivity. CN BrJFeBr,
10. Nitril group, -CN, is a meta director. Predict the product for the following reaction, by proposing a plausible mechanism. Make sure show resonance structures to explain selectivity. CN BrJFeBr,
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:**Title: Understanding the Selectivity of Meta Directors in Electrophilic Aromatic Substitution**
**Problem 10: Nitrile Group as a Meta Director**
**Objective:**
Predict the product for an electrophilic aromatic substitution reaction involving a nitrile-substituted benzene compound by proposing a plausible mechanism and using resonance structures to explain selectivity.
**Reaction Details:**
- **Reactant:** Benzene ring with a nitrile group (–CN) attached.
- **Reagent:** Bromine (Br₂) with iron(III) bromide (FeBr₃) catalyst.
**Instructions:**
The nitrile group, –CN, is known to be a meta director in electrophilic aromatic substitution reactions. This means that any incoming substituent will most likely attach to the meta position relative to the –CN group.
**Step-by-step Approach:**
1. **Identify the Directing Effect:**
- Recognize the nitrile group's effect as an electron-withdrawing group, which makes it a meta director. This is due to its ability to stabilize the intermediate cation during the reaction by resonance and inductive effects.
2. **Predict the Product:**
- Given that –CN directs to the meta position, predict the preferred site for bromination on the benzene ring.
3. **Mechanism Explanation:**
- Use resonance structures to illustrate how the electron-withdrawing nitrile group stabilizes the sigma complex intermediate of the meta-substituted reaction pathway.
4. **Draw the Product:**
- Show the final structure with bromine (Br) added to the meta position in relation to the nitrile group on the benzene ring.
**Conclusion:**
This exercise demonstrates the role of substituents in directing the outcome of electrophilic aromatic substitution reactions. Understanding these principles is essential for predicting reaction products in aromatic chemistry.
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