Consider the following molecules: OH Он ČI B Which is the stronger acid? Which structural effect led you to that answer? (If more than one effect is present, select the more significant effect)
Consider the following molecules: OH Он ČI B Which is the stronger acid? Which structural effect led you to that answer? (If more than one effect is present, select the more significant effect)
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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- **Molecule A:**
- Contains a benzene ring (six-membered carbon ring with alternating double bonds).
- A hydroxyl group (OH) is attached to one of the carbon atoms.
- A chlorine (Cl) atom is attached to the carbon atom in the para position (opposite) relative to the hydroxyl group.
- **Molecule B:**
- Contains a benzene ring (six-membered carbon ring with alternating double bonds).
- A hydroxyl group (OH) is attached to one of the carbon atoms.
- No other substituents are present on the benzene ring.
**Questions to Consider:**
1. **Which is the stronger acid?**
2. **Which structural effect led you to that answer?**
- If more than one effect is present, select the more significant effect.
**Detailed Explanation:**
The strength of an acid in aromatic compounds such as these can be influenced by the substituents present on the benzene ring. Chlorine, being an electron-withdrawing group via inductive effect and slightly through resonance, can have a significant impact on the acidity of phenol (the base structure of molecule A and B). The presence of chlorine tends to stabilize the conjugate base of the acid, making it more likely to donate a proton (H+), hence increasing the acidity. Thus, analyze the molecules with respect to the position of electron-withdrawing groups and consider their effects on acidity.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F4167b07b-ab2c-42e3-ab89-9f12261de975%2Fc0ddd38e-9334-4366-92c6-28fdefdcb8d9%2Fo86tupg_processed.png&w=3840&q=75)
Transcribed Image Text:**Consider the following molecules:**
- **Molecule A:**
- Contains a benzene ring (six-membered carbon ring with alternating double bonds).
- A hydroxyl group (OH) is attached to one of the carbon atoms.
- A chlorine (Cl) atom is attached to the carbon atom in the para position (opposite) relative to the hydroxyl group.
- **Molecule B:**
- Contains a benzene ring (six-membered carbon ring with alternating double bonds).
- A hydroxyl group (OH) is attached to one of the carbon atoms.
- No other substituents are present on the benzene ring.
**Questions to Consider:**
1. **Which is the stronger acid?**
2. **Which structural effect led you to that answer?**
- If more than one effect is present, select the more significant effect.
**Detailed Explanation:**
The strength of an acid in aromatic compounds such as these can be influenced by the substituents present on the benzene ring. Chlorine, being an electron-withdrawing group via inductive effect and slightly through resonance, can have a significant impact on the acidity of phenol (the base structure of molecule A and B). The presence of chlorine tends to stabilize the conjugate base of the acid, making it more likely to donate a proton (H+), hence increasing the acidity. Thus, analyze the molecules with respect to the position of electron-withdrawing groups and consider their effects on acidity.
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