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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![**Question 5:**
**Objective:**
Arrange the following compounds according to **INCREASING** reactivity towards Bromination (via Electrophilic Aromatic Substitution, EAS).
**Compounds:**
- **Compound A:** Chlorobenzene (benzene ring with a chlorine atom attached).
- **Compound B:** Ethylbenzene (benzene ring with an ethyl group attached).
- **Compound C:** 1-Chloro-2-phenylethane (benzene ring with a chlorine atom and an ethyl group attached).
- **Compound D:** Benzonitrile (benzene ring with a nitrile group attached).
- **Compound E:** N,N-Dimethylaniline (benzene ring with an amine group attached in its protonated form).
**Diagram:**
A sequence of blank boxes is presented with inequality signs between them to indicate the order of reactivity:
**Reactivity:**
\[ \text{Blank} \ < \ \text{Blank} \ < \ \text{Blank} \ < \ \text{Blank} \ < \ \text{Blank} \]
Each blank is to be filled with one of the compounds (A, B, C, D, E) based on their increasing reactivity toward bromination via EAS.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fce17c6ae-9240-4648-8795-951aa382f408%2Fa09fd66d-0e28-48b1-a975-e29943fdd4da%2F0ug9tcg_processed.png&w=3840&q=75)
Transcribed Image Text:**Question 5:**
**Objective:**
Arrange the following compounds according to **INCREASING** reactivity towards Bromination (via Electrophilic Aromatic Substitution, EAS).
**Compounds:**
- **Compound A:** Chlorobenzene (benzene ring with a chlorine atom attached).
- **Compound B:** Ethylbenzene (benzene ring with an ethyl group attached).
- **Compound C:** 1-Chloro-2-phenylethane (benzene ring with a chlorine atom and an ethyl group attached).
- **Compound D:** Benzonitrile (benzene ring with a nitrile group attached).
- **Compound E:** N,N-Dimethylaniline (benzene ring with an amine group attached in its protonated form).
**Diagram:**
A sequence of blank boxes is presented with inequality signs between them to indicate the order of reactivity:
**Reactivity:**
\[ \text{Blank} \ < \ \text{Blank} \ < \ \text{Blank} \ < \ \text{Blank} \ < \ \text{Blank} \]
Each blank is to be filled with one of the compounds (A, B, C, D, E) based on their increasing reactivity toward bromination via EAS.
Expert Solution
Step 1
Electrophilic bromination of phenyl ring depends on electron density on phenyl ring, which vary with the substitution on the ring.
Amine group is strong activating group using lone pair on the nitrogen.
Other hand nitrile group is the most deactivating group as it withdraw electron via resonance.
Ethyl group is weak activating and -Cl is weak deactivating group.
Now when ethyl and -Cl group present in the same ring then it's show intermediate activity toward bromination.
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