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:
Which would be the best leaving group in the following compound for an SN1 mechanism?
### Compound Structure:
The given compound has the following structure:
- A central carbon chain with substituents.
- Substituents on the central chain include: Br, OH, OH2+, Me, HO, and TsO.
#### Structural Representation:
```plaintext
Br
|
TsO - C - C - Me
| |
OH OH2+
|
HO
```
Here, "TsO" represents a tosyl group.
### Multiple Choice Options:
- ☐ Br
- ☐ OH
- ☐ OH2+
- ☐ OTs
In this structure:
- "Br" stands for Bromine
- "OH" stands for Hydroxyl group
- "OH2+" is a protonated hydroxyl group
- "OTs" stands for Tosylate
### Detailed Analysis of Options:
1. **Br (Bromine):**
- Bromine is a good leaving group in various organic reactions due to its ability to stabilize the negative charge when it leaves.
2. **OH (Hydroxyl Group):**
- The OH group is generally a poor leaving group in SN1 reactions because it forms a highly reactive hydroxide ion (OH-).
3. **OH2+ (Protonated Hydroxyl Group):**
- Once protonated, water (H2O) becomes a very good leaving group in SN1 reactions because it is neutral and stable upon departure.
4. **OTs (Tosylate):**
- Tosylate is an excellent leaving group in many substitution reactions including SN1 due to the resonance stabilization of the tosylate anion.
### Answer:
The best leaving group in an SN1 mechanism for the given compound is:
- ☐ Br
- ☐ OH
- ☑️ OH2+
- ☐ OTs
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