E. Rank the following molecules in decreasing activation (from most activated =1 to most deactivated =6) based on the substituents present on the benzene ring. Also indicate whether the substituents are ortho-para or meta directors. HO -NH₂ CI
E. Rank the following molecules in decreasing activation (from most activated =1 to most deactivated =6) based on the substituents present on the benzene ring. Also indicate whether the substituents are ortho-para or meta directors. HO -NH₂ CI
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:**Question E: Ranking of Benzene Derivatives by Activation and Directive Properties**
**Objective:** Rank the following molecules in decreasing order of activation (from most activated, assigned a rank of 1, to most deactivated, assigned a rank of 6) based on the substituents present on the benzene ring. Also, indicate whether the substituents are ortho-para or meta directors.
**Molecules Provided:**
1. **Molecule A:** Benzoic acid (benzene ring with a carboxyl group, -COOH)
2. **Molecule B:** Isopropylbenzene (benzene ring with an isopropyl group, -CH(CH₃)₂)
3. **Molecule C:** Nitrobenzene (benzene ring with a nitro group, -NO₂)
4. **Molecule D:** Aniline (benzene ring with an amino group, -NH₂)
5. **Molecule E:** Chlorobenzene (benzene ring with a chloro group, -Cl)
6. **Molecule F:** Benzyl acetate (benzene ring with an acetoxy group, -OCOCH₃)
**Instructions for Ranking and Directive Properties:**
- **Activation trend:** The activation or deactivation of the benzene ring depends on the substituent’s electronic effects. Electron-donating groups (EDGs) activate the ring, whereas electron-withdrawing groups (EWGs) deactivate the ring.
- **Directive properties:** Substituents can be either ortho-para directors (EDGs usually) or meta directors (EWGs usually).
**Analyzed Details:**
1. **Aniline (-NH₂):**
- **Activation:** Strong electron-donating group.
- **Directive Property:** Ortho-para director.
- **Rank:** 1 (most activated).
2. **Isopropylbenzene (-CH(CH₃)₂):**
- **Activation:** Moderately electron-donating group.
- **Directive Property:** Ortho-para director.
- **Rank:** 2.
3. **Chlorobenzene (-Cl):**
- **Activation:** Weakly deactivating group (due to inductive withdrawal but resonance donation).
- **Directive Property:** Ortho-para director.
- **Rank:** 3.
4. **Benzoic acid (-COOH):**
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