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.
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.
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.
- [ ] \( R,R \).
- [ ] \( R \).
- [x] racemic.
**Note:** The option "racemic" is selected, indicating the presence of an equal mixture of enantiomers. The answer is marked as "Incorrect," implying that the selected characteristic is not the right description for the product(s) of the reaction in question.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fc1ac5224-ae90-47cf-a0ff-6d2ed7449d0c%2Fdeccc2ee-850e-4fe4-825c-b35c6fab2392%2Feunoubh_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.
- [ ] \( R,R \).
- [ ] \( R \).
- [x] racemic.
**Note:** The option "racemic" is selected, indicating the presence of an equal mixture of enantiomers. The answer is marked as "Incorrect," implying that the selected characteristic is not the right description for the product(s) of the reaction in question.
![### Educational Content: Hydroboration-Oxidation of Alkenes
**Alkene to Alcohol Conversion via Hydroboration-Oxidation**
Alkenes can be transformed into alcohols through a two-step hydroboration-oxidation process. This reaction involves the addition of borane (BH₃) followed by oxidation.
#### Reaction Sequence
1. **Reactants and Conditions:**
- **Step 1:** Borane (B₂H₆) in diglyme (a solvent)
- **Step 2:** Hydrogen peroxide (H₂O₂) with a hydroxide ion (HO⁻) in water (H₂O)
2. **Reaction Details:**
- An alkene undergoes an initial treatment with borane, leading to the addition of boron and hydrogen across the double bond.
- The second step involves the oxidation where the boron atom is replaced by a hydroxyl group (-OH) using hydrogen peroxide.
#### Structure and Stereochemistry
- **Stereochemistry Indication:** Clearly indicate the stereochemistry of the resulting alcohol by using a wedged bond (to show bonds coming out of the plane), a dashed bond (representing bonds going behind the plane), and two in-plane bonds at each chiral carbon.
- **Product Structure:**
- Two alcohols are formed from the reaction of cyclohexene:
1. **First Product:** The hydroxyl group and one hydrogen are on adjacent carbons, both depicted with wedged bonds, indicating their stereochemistry.
2. **Second Product:** Similar structure with the hydroxyl group and hydrogen having changed positions.
#### Diagram Explanation
- The left side of the diagram shows the initial cyclohexene molecule with a double bond.
- The reaction conditions are listed with arrows indicating the reaction progression.
- The right side of the diagram illustrates the two possible stereoisomeric alcohol products, emphasizing the spatial arrangement of the OH group and hydrogen atom.
*Note: Be sure to draw hydrogens on the oxygen where applicable, which is crucial for understanding molecular geometry and stereochemistry.*
This educational resource helps in visualizing the transformation from alkenes to alcohols and the importance of stereochemistry in such reactions.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fc1ac5224-ae90-47cf-a0ff-6d2ed7449d0c%2Fdeccc2ee-850e-4fe4-825c-b35c6fab2392%2F7ulo03b_processed.jpeg&w=3840&q=75)
Transcribed Image Text:### Educational Content: Hydroboration-Oxidation of Alkenes
**Alkene to Alcohol Conversion via Hydroboration-Oxidation**
Alkenes can be transformed into alcohols through a two-step hydroboration-oxidation process. This reaction involves the addition of borane (BH₃) followed by oxidation.
#### Reaction Sequence
1. **Reactants and Conditions:**
- **Step 1:** Borane (B₂H₆) in diglyme (a solvent)
- **Step 2:** Hydrogen peroxide (H₂O₂) with a hydroxide ion (HO⁻) in water (H₂O)
2. **Reaction Details:**
- An alkene undergoes an initial treatment with borane, leading to the addition of boron and hydrogen across the double bond.
- The second step involves the oxidation where the boron atom is replaced by a hydroxyl group (-OH) using hydrogen peroxide.
#### Structure and Stereochemistry
- **Stereochemistry Indication:** Clearly indicate the stereochemistry of the resulting alcohol by using a wedged bond (to show bonds coming out of the plane), a dashed bond (representing bonds going behind the plane), and two in-plane bonds at each chiral carbon.
- **Product Structure:**
- Two alcohols are formed from the reaction of cyclohexene:
1. **First Product:** The hydroxyl group and one hydrogen are on adjacent carbons, both depicted with wedged bonds, indicating their stereochemistry.
2. **Second Product:** Similar structure with the hydroxyl group and hydrogen having changed positions.
#### Diagram Explanation
- The left side of the diagram shows the initial cyclohexene molecule with a double bond.
- The reaction conditions are listed with arrows indicating the reaction progression.
- The right side of the diagram illustrates the two possible stereoisomeric alcohol products, emphasizing the spatial arrangement of the OH group and hydrogen atom.
*Note: Be sure to draw hydrogens on the oxygen where applicable, which is crucial for understanding molecular geometry and stereochemistry.*
This educational resource helps in visualizing the transformation from alkenes to alcohols and the importance of stereochemistry in such reactions.
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