Which is the best method for the following transformation? OH A. 1. BH3, THF 2. H₂O₂, OH- B. H¹, H₂O C. concentrated H₂SO4 D. 1. Hg(OAc)2, H₂O 2. NaBH4
Which is the best method for the following transformation? OH A. 1. BH3, THF 2. H₂O₂, OH- B. H¹, H₂O C. concentrated H₂SO4 D. 1. Hg(OAc)2, H₂O 2. NaBH4
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 is the best method for the following transformation?
### Diagram:
The diagram depicts a chemical reaction where an alkene is converted to an alcohol. The structure on the left is an alkene with a double bond between two carbon atoms (one of which is a methane group), and the structure on the right is an alcohol where the OH group is attached to what was the formerly double-bonded carbon.
```
H3C-CH=CH2 → H3C-CH(OH)-CH3
```
### Options:
A.
1. BH₃, THF
2. H₂O₂, OH⁻
B.
H⁺, H₂O
C.
Concentrated H₂SO₄
D.
1. Hg(OAc)₂, H₂O
2. NaBH₄
## Explanation:
### Option A:
The combination of BH₃ (borane) in THF (tetrahydrofuran) followed by H₂O₂ (hydrogen peroxide) and OH⁻ (hydroxide ion) is usually indicative of hydroboration-oxidation. This method results in the anti-Markovnikov addition of water (OH and H), where the hydroxyl group attaches to the less substituted carbon atom.
### Option B:
Using H⁺ (proton, typically in the form of an acid) and H₂O (water) usually leads to the Markovnikov addition of water to the double bond, where the hydroxyl group attaches to the more substituted carbon atom.
### Option C:
Concentrated H₂SO₄ (sulfuric acid) can be used for acid-catalyzed hydration of alkenes, which typically follows Markovnikov's rule.
### Option D:
The use of Hg(OAc)₂, H₂O followed by NaBH₄ (sodium borohydride) describes an oxymercuration-demercuration reaction. This method also results in Markovnikov addition of water without rearrangements.
---
### Conclusion:
For converting an alkene to an alcohol with the anti-Markovnikov orientation, the best method is **Option A** (1. BH₃, THF 2. H₂O₂, OH⁻).
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