### Educational Explanation: Conversion of Alkenes to Alcohols via Hydroboration-OxidationIn this exercise, alkenes are converted to alcohols through the hydroboration-oxidation reaction sequence. The task is to:(a) Draw the structure of the alcohol or alcohols formed in the reaction sequence and clearly indicate stereochemistry by drawing a wedged bond, a dashed bond, and two in-plane bonds for each chiral carbon. Be sure to draw hydrogen atoms connected to wedge and dash bonds, as well as oxygen where applicable.(b) Characterize the products of the reactions. #### Reaction Sequence1. **Hydroboration**: - Reagents: \( B_2H_6 \), diglyme - This step involves the addition of boron and hydrogen across the double bond of an alkene.2. **Oxidation**: - Reagents: \( H_2O_2 \), \( HO^- \), \( H_2O \) - The boron atom is replaced by a hydroxyl group (\(-OH\)).#### Structure and Stereochemistry- The first diagram shows a cyclohexene molecule as the starting alkene.- In the second set of diagrams, the products formed are cyclohexanol derivatives with different stereochemistries: 1. **Left Structure**: - The hydroxyl group (\(-OH\)) is on a wedge, indicating it is positioned above the plane of the ring. - A hydrogen atom is on a dashed line, indicating it is positioned below the plane. 2. **Right Structure**: - The hydroxyl group (\(-OH\)) is above the plane, but the positions of substituents differ, resulting in an isomer.Each structure illustrates different stereochemical outcomes of the reaction, reflecting how the initial addition of boron and subsequent oxidation can produce distinct configurations of alcohols.#### Key Points to Consider:- **Stereochemistry**: Understanding how groups are added in three-dimensional space is crucial. The orientation (wedged, dashed, in-plane) affects the physical and chemical properties of the compound.- **Reaction Mechanism**: The hydroboration step adds elements syn (on the same side), while oxidation replaces boron with hydroxyl without rearranging the stereocenter.Through this method, alkenes can be effectively transformed into

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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. 1. B2H6, diglyme (a) 2. H2O2, HO¯, H20 OH OH H

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. 1. B2H6, diglyme (a) 2. H2O2, HO¯, H20 OH OH H

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

### Educational Explanation: Conversion of Alkenes to Alcohols via Hydroboration-Oxidation

In this exercise, alkenes are converted to alcohols through the hydroboration-oxidation reaction sequence. The task is to:

(a) Draw the structure of the alcohol or alcohols formed in the reaction sequence and clearly indicate stereochemistry by drawing a wedged bond, a dashed bond, and two in-plane bonds for each chiral carbon. Be sure to draw hydrogen atoms connected to wedge and dash bonds, as well as oxygen where applicable.

(b) Characterize the products of the reactions.

#### Reaction Sequence

1. **Hydroboration**:
- Reagents: \( B_2H_6 \), diglyme
- This step involves the addition of boron and hydrogen across the double bond of an alkene.

2. **Oxidation**:
- Reagents: \( H_2O_2 \), \( HO^- \), \( H_2O \)
- The boron atom is replaced by a hydroxyl group (\(-OH\)).

#### Structure and Stereochemistry

- The first diagram shows a cyclohexene molecule as the starting alkene.
- In the second set of diagrams, the products formed are cyclohexanol derivatives with different stereochemistries:
1. **Left Structure**:
- The hydroxyl group (\(-OH\)) is on a wedge, indicating it is positioned above the plane of the ring.
- A hydrogen atom is on a dashed line, indicating it is positioned below the plane.
2. **Right Structure**:
- The hydroxyl group (\(-OH\)) is above the plane, but the positions of substituents differ, resulting in an isomer.

Each structure illustrates different stereochemical outcomes of the reaction, reflecting how the initial addition of boron and subsequent oxidation can produce distinct configurations of alcohols.

#### Key Points to Consider:

- **Stereochemistry**: Understanding how groups are added in three-dimensional space is crucial. The orientation (wedged, dashed, in-plane) affects the physical and chemical properties of the compound.
- **Reaction Mechanism**: The hydroboration step adds elements syn (on the same side), while oxidation replaces boron with hydroxyl without rearranging the stereocenter.

Through this method, alkenes can be effectively transformed into

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