Alkenes can be converted to alcohols by hydroboration-oxidation. (a) Draw the structure of the alcohol or alcohols formed in the reaction sequence. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two in-plane bonds per each chiral carbon. Draw hydrogen atoms that are connected to wedge-and-dash bonds.(b) Characterize the product or products of the reactions. Be sure to draw hydrogens on oxygen, where applicable. Select Draw Rings More Erase C H 1. B2H6, diglyme (а) 2. Н.О2, НО"-, H20
Alkenes can be converted to alcohols by hydroboration-oxidation. (a) Draw the structure of the alcohol or alcohols formed in the reaction sequence. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two in-plane bonds per each chiral carbon. Draw hydrogen atoms that are connected to wedge-and-dash bonds.(b) Characterize the product or products of the reactions. Be sure to draw hydrogens on oxygen, where applicable. Select Draw Rings More Erase C H 1. B2H6, diglyme (а) 2. Н.О2, НО"-, H20
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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![**Question:**
(b) The product or products of the reaction are characterized as being
- [ ] achiral
- [ ] R, S (and/or S, R)
- [ ] S
- [ ] S, S
- [ ] diastereomers
- [ ] R, R
- [ ] R
- [ ] racemic](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fc1ac5224-ae90-47cf-a0ff-6d2ed7449d0c%2Fe734a9d9-33c4-48da-9986-a38ef3aecd7a%2Fn285onl_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Question:**
(b) The product or products of the reaction are characterized as being
- [ ] achiral
- [ ] R, S (and/or S, R)
- [ ] S
- [ ] S, S
- [ ] diastereomers
- [ ] R, R
- [ ] R
- [ ] racemic
![**Educational Content on Alkene Hydroboration-Oxidation**
**Introduction:**
Alkenes can undergo a transformation to become alcohols through the process of hydroboration-oxidation. This reaction sequence is significant in organic chemistry for its ability to convert double bonds into alcohols with specific stereochemistry.
**Reaction Details:**
1. **Reactant:** The starting material is an alkene. The structure shown is cyclohexene, which features a six-membered carbon ring with a double bond.
2. **Reaction Conditions:**
- **Step 1:** The alkene is treated with borane (BH₃) in the presence of diglyme (a solvent). This step is known as hydroboration, where boron adds across the double bond.
- **Step 2:** The boron-containing intermediate is reacted with hydrogen peroxide (H₂O₂) and hydroxide ions (OH⁻) in water. This stage, known as oxidation, replaces boron with a hydroxyl group, converting the alkene into an alcohol.
**Instructions for Representation:**
- **Structure Drawing:** When depicting the alcohol product, clearly indicate stereochemistry using bond representations:
- **Wedge Bond:** Represents a bond coming out of the plane towards the viewer.
- **Dash Bond:** Represents a bond going into the plane away from the viewer.
- **In-plane Bonds:** Used for bonds lying flat in the plane of the drawing.
- **Hydrogen Atoms:** Ensure to draw hydrogen atoms connected to the chiral centers or as specified in the chemical structure.
**Diagram Explanation:**
The diagram illustrates the chemical reaction of cyclohexene (hexagonal structure with a double bond) undergoing conversion to the corresponding alcohol. The reagents are listed alongside arrows indicating the sequence of steps involved in the transformation.
**Conclusion:**
This hydroboration-oxidation process is crucial for obtaining alcohols with controlled stereochemistry from alkenes, a fundamental transformation in organic synthesis. Understanding this reaction helps in predicting the outcome and configurations of organic compounds in chemical research and industry.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fc1ac5224-ae90-47cf-a0ff-6d2ed7449d0c%2Fe734a9d9-33c4-48da-9986-a38ef3aecd7a%2Fw75v48_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Educational Content on Alkene Hydroboration-Oxidation**
**Introduction:**
Alkenes can undergo a transformation to become alcohols through the process of hydroboration-oxidation. This reaction sequence is significant in organic chemistry for its ability to convert double bonds into alcohols with specific stereochemistry.
**Reaction Details:**
1. **Reactant:** The starting material is an alkene. The structure shown is cyclohexene, which features a six-membered carbon ring with a double bond.
2. **Reaction Conditions:**
- **Step 1:** The alkene is treated with borane (BH₃) in the presence of diglyme (a solvent). This step is known as hydroboration, where boron adds across the double bond.
- **Step 2:** The boron-containing intermediate is reacted with hydrogen peroxide (H₂O₂) and hydroxide ions (OH⁻) in water. This stage, known as oxidation, replaces boron with a hydroxyl group, converting the alkene into an alcohol.
**Instructions for Representation:**
- **Structure Drawing:** When depicting the alcohol product, clearly indicate stereochemistry using bond representations:
- **Wedge Bond:** Represents a bond coming out of the plane towards the viewer.
- **Dash Bond:** Represents a bond going into the plane away from the viewer.
- **In-plane Bonds:** Used for bonds lying flat in the plane of the drawing.
- **Hydrogen Atoms:** Ensure to draw hydrogen atoms connected to the chiral centers or as specified in the chemical structure.
**Diagram Explanation:**
The diagram illustrates the chemical reaction of cyclohexene (hexagonal structure with a double bond) undergoing conversion to the corresponding alcohol. The reagents are listed alongside arrows indicating the sequence of steps involved in the transformation.
**Conclusion:**
This hydroboration-oxidation process is crucial for obtaining alcohols with controlled stereochemistry from alkenes, a fundamental transformation in organic synthesis. Understanding this reaction helps in predicting the outcome and configurations of organic compounds in chemical research and industry.
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