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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
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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**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.
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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