Н. H3C Н н offod bnuor Im- л H-B . I BH3 THF 1. BH3, THF 2. NaOH, H2O2 Hi Н Н H“Y H3C H3C Jogros sohlenomyanu ns iconod elduob Н 7+ H Н ОН BH₂ H Н NaOH H2O2 Н ОН "Н"н HW H3C Н nodiso s of ebbs XH
Н. H3C Н н offod bnuor Im- л H-B . I BH3 THF 1. BH3, THF 2. NaOH, H2O2 Hi Н Н H“Y H3C H3C Jogros sohlenomyanu ns iconod elduob Н 7+ H Н ОН BH₂ H Н NaOH H2O2 Н ОН "Н"н HW H3C Н nodiso s of ebbs XH
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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Draw the two structures for the markovnikov and anti-markovnikov products possible from this reaction. How do you know if the product made is markovnikov or anti-markovnikov?
Transcribed Image Text:### Hydroboration-Oxidation Reaction of an Alkene
**Reaction Overview:**
This image illustrates the hydroboration-oxidation of an alkene to form an alcohol.
**Mechanism Steps:**
1. **Hydroboration:**
- **Reagents:** BH₃ (borane) in THF (tetrahydrofuran)
- The alkene (CH₂=CHCH₃) reacts with BH₃.
- A transition state complex is formed where boron (B) adds to the less substituted carbon, and hydrogen (H) adds to the more substituted carbon of the double bond, following anti-Markovnikov's rule.
- This results in an organoborane intermediate.
2. **Oxidation:**
- **Reagents:** NaOH (sodium hydroxide) and H₂O₂ (hydrogen peroxide)
- The organoborane intermediate is treated with NaOH and H₂O₂.
- The boron group is replaced by an hydroxyl group (OH), producing the alcohol.
**Final Product:**
The alcohol obtained has the OH group attached to the less substituted carbon of the original double bond.
This reaction is a key method for converting alkenes into alcohols with anti-Markovnikov selectivity, meaning the addition of the OH group occurs at the end of the molecular chain, opposite from the more substituted carbon.
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