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:The image presents a chemical reaction question, which asks to identify the major organic product formed under specific conditions. The reactant is propene, represented as a three-carbon alkene with a double bond.
**Reagents and Conditions:**
1. BH₃·THF (Borane in Tetrahydrofuran)
2. NaOH, H₂O₂ (Sodium Hydroxide, Hydrogen Peroxide)
**Reaction Description:**
This is a hydroboration-oxidation reaction, a common method for converting alkenes to alcohols.
**Product Choices:**
Four structural options are provided for selection:
1. A primary alcohol with the hydroxyl group on the terminal carbon.
2. A secondary alcohol with the hydroxyl group on the middle carbon.
3. An organoborane intermediate with BH₂ attached to the terminal carbon.
4. A diol containing two hydroxyl groups.
The correct choice for this reaction is the primary alcohol, where the hydroxyl group is added to the less substituted carbon, illustrating anti-Markovnikov addition typical of hydroboration-oxidation reactions.

Transcribed Image Text:**Explanation of Reaction and Potential Major Products:**
In this exercise, we are asked to determine the major product of the given reaction, where a dibenzyl is exposed to osmium tetroxide (OsO₄) followed by sodium bisulfite (NaHSO₃) in water. This process typically results in the conversion of alkenes to diols by syn-dihydroxylation.
### Reaction Details:
- **Reagents:**
1. **OsO₄** (Osmium tetroxide)
2. **NaHSO₃, H₂O** (Sodium bisulfite in water)
- **Mechanism:**
The osmium tetroxide adds to the double bond in a syn addition manner, leading to the formation of a cyclic osmate ester intermediate, which is subsequently hydrolyzed by sodium bisulfite to give a vicinal diol.
### Options for Major Products:
1. **Option 1:**
- Structure: Two adjacent carbon atoms each bonded to a hydroxyl group, showing syn addition as both -OH groups are on the same side. Phenyl groups (Ph) are also present, indicating the presence of benzene rings.
2. **Option 2:**
- Structure: Similar to option 1, with stereochemistry indicating syn addition but with different orientation. Phenyl groups are shown.
3. **Option 3:**
- Structure: An epoxide ring is suggested here. This indicates a different pathway and is not the expected outcome with OsO₄.
4. **Option 4:**
- Structure: Suggests the formation of an open chain with additional phenyl groups which is unlikely under these conditions.
5. **Option 5:**
- Structure: Another epoxide, similar to option 3, which is less likely here.
6. **Option 6:**
- Statement: No reaction under these conditions or the correct product is not listed.
### Conclusion:
- **Expected Outcome:**
This reaction most likely leads to a syn-diol formation on the alkenes, specified in options 1 or 2. The reaction condition and reagents strongly support syn addition of hydroxyl groups.
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