3. Acidity Assessment! Rank the following acids in order from weakest acid to strongest acid. Explain why you ranked the acids in the designated order. Your answer should include, if applicable, reasons based in inductive effects, resonance (EDG vs. EWG), etc. Он но NH2 HO CI А В D E V V V
3. Acidity Assessment! Rank the following acids in order from weakest acid to strongest acid. Explain why you ranked the acids in the designated order. Your answer should include, if applicable, reasons based in inductive effects, resonance (EDG vs. EWG), etc. Он но NH2 HO CI А В D E V V V
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...
Related questions
Question
Rank the following acids in order from weakest acid to strongest acid. Explain why you ranked the acids in the designated order. Your answer should include, if applicable, reasons based in inductive effects, resonance (electron donating groups vs electron withdrawing groups), etc.
![**Acidity Assessment**
**Task:** Rank the following acids in order from weakest acid to strongest acid. Provide an explanation for your ranking, including relevant reasons based on inductive effects, resonance (Electron Donating Groups (EDG) vs. Electron Withdrawing Groups (EWG)), etc.
**Compounds:**
- **A:** Benzene ring with an OH group (Phenol)
- **B:** Cyclohexane with an OH group
- **C:** Benzene ring with an OH group and a Cl group positioned ortho to each other
- **D:** Cyclohexane with a NH₂ group
- **E:** Benzene ring with an OH group and a carbonyl group adjacent to each other
**Ranking Order:**
\[ \text{B} < \text{D} < \text{A} < \text{C} < \text{E} \]
**Considerations for Ranking:**
1. **Inductive Effect:**
- Electron withdrawing groups (EWG) like Cl can stabilize the negative charge on the conjugate base, enhancing acidity.
- Electron donating groups (EDG) like NH₂ can destabilize the negative charge on the conjugate base, reducing acidity.
2. **Resonance:**
- Molecules with resonance stabilization in the conjugate base are generally more acidic because the negative charge can be delocalized.
3. **Structural Stability:**
- Aromatic compounds often show increased acidity due to resonance compared to non-aromatic counterparts.
**Explanation:**
- **B (Cyclohexanol):** Least acidic; lacks delocalization or electron withdrawing effects.
- **D (Cyclohexylamine):** Slightly more acidic than B due to NH₂, but still relatively weak.
- **A (Phenol):** More acidic than non-aromatic compounds due to resonance stabilization.
- **C (Chlorophenol):** Cl as an EWG increases acidity over phenol by stabilizing the conjugate base.
- **E (Acetylphenol):** Strongest acid; the carbonyl group is a strong EWG and enhances the acidity via resonance and induction.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F9fa0ca06-dd60-4896-86b5-5c6179a72eaa%2Fe3aee664-14f1-4723-8545-b17e0527f60c%2F9a21vsd_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Acidity Assessment**
**Task:** Rank the following acids in order from weakest acid to strongest acid. Provide an explanation for your ranking, including relevant reasons based on inductive effects, resonance (Electron Donating Groups (EDG) vs. Electron Withdrawing Groups (EWG)), etc.
**Compounds:**
- **A:** Benzene ring with an OH group (Phenol)
- **B:** Cyclohexane with an OH group
- **C:** Benzene ring with an OH group and a Cl group positioned ortho to each other
- **D:** Cyclohexane with a NH₂ group
- **E:** Benzene ring with an OH group and a carbonyl group adjacent to each other
**Ranking Order:**
\[ \text{B} < \text{D} < \text{A} < \text{C} < \text{E} \]
**Considerations for Ranking:**
1. **Inductive Effect:**
- Electron withdrawing groups (EWG) like Cl can stabilize the negative charge on the conjugate base, enhancing acidity.
- Electron donating groups (EDG) like NH₂ can destabilize the negative charge on the conjugate base, reducing acidity.
2. **Resonance:**
- Molecules with resonance stabilization in the conjugate base are generally more acidic because the negative charge can be delocalized.
3. **Structural Stability:**
- Aromatic compounds often show increased acidity due to resonance compared to non-aromatic counterparts.
**Explanation:**
- **B (Cyclohexanol):** Least acidic; lacks delocalization or electron withdrawing effects.
- **D (Cyclohexylamine):** Slightly more acidic than B due to NH₂, but still relatively weak.
- **A (Phenol):** More acidic than non-aromatic compounds due to resonance stabilization.
- **C (Chlorophenol):** Cl as an EWG increases acidity over phenol by stabilizing the conjugate base.
- **E (Acetylphenol):** Strongest acid; the carbonyl group is a strong EWG and enhances the acidity via resonance and induction.
Expert Solution
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 2 steps with 2 images
Recommended textbooks for you
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY