**Title:** Conversion of Alkenes to Alcohols via Hydroboration-Oxidation**Content:**Alkenes can be converted to alcohols by hydroboration-oxidation. This process involves two main steps using specific reagents to transform an alkene into an alcohol, while stereochemistry and the precise addition of groups are carefully controlled.**Chemical Reaction and Mechanism:**1. **Initial Reactant:** - The starting material is a cyclohexene ring, which contains a carbon-carbon double bond, making it an alkene.2. **Reaction Sequence:** - **Step 1:** The alkene undergoes hydroboration using \( \text{B}_2\text{H}_6 \) and diglyme. In this step, boron adds to the least substituted carbon of the alkene in a syn-addition manner. - **Step 2:** The organoborane intermediate is then oxidized by hydrogen peroxide (\( \text{H}_2\text{O}_2 \)), in the presence of hydroxide ions (\( \text{HO}^- \)), and water (\( \text{H}_2\text{O} \)). This converts the boron group to a hydroxyl group (\( \text{OH} \)), completing the transformation to alcohol.**Stereochemistry:**Clearly indicate stereochemistry by employing a wedged bond for groups projecting outwards, a dashed bond for groups projecting inwards, and two in-plane bonds for groups that lie in the plane of the paper, around each chiral carbon. Hydrogen atoms connected to wedge-and-dash bonds must be explicitly shown to reflect accurate stereochemistry.**Interactive Component:**The diagram provides tools to draw and modify molecular structures, including:- Lines for drawing bonds.- Wedges and dashes for stereochemistry.- Options to add specific atoms such as carbon (C), hydrogen (H), and oxygen (O).This precise depiction of molecular configurations is crucial for understanding the spatial arrangement and physical properties of the resultant alcohols. By following this reaction path and noting stereochemistry, students gain insight into how structural changes occur in organic reactions, enhancing their understanding of molecular transformations.

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 1. B2H6, diglyme (a) 2. H2O2, HO, 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 1. B2H6, diglyme (a) 2. H2O2, HO, 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

**Title:** Conversion of Alkenes to Alcohols via Hydroboration-Oxidation

**Content:**

Alkenes can be converted to alcohols by hydroboration-oxidation. This process involves two main steps using specific reagents to transform an alkene into an alcohol, while stereochemistry and the precise addition of groups are carefully controlled.

**Chemical Reaction and Mechanism:**

1. **Initial Reactant:**
- The starting material is a cyclohexene ring, which contains a carbon-carbon double bond, making it an alkene.

2. **Reaction Sequence:**
- **Step 1:** The alkene undergoes hydroboration using \( \text{B}_2\text{H}_6 \) and diglyme. In this step, boron adds to the least substituted carbon of the alkene in a syn-addition manner.
- **Step 2:** The organoborane intermediate is then oxidized by hydrogen peroxide (\( \text{H}_2\text{O}_2 \)), in the presence of hydroxide ions (\( \text{HO}^- \)), and water (\( \text{H}_2\text{O} \)). This converts the boron group to a hydroxyl group (\( \text{OH} \)), completing the transformation to alcohol.

**Stereochemistry:**

Clearly indicate stereochemistry by employing a wedged bond for groups projecting outwards, a dashed bond for groups projecting inwards, and two in-plane bonds for groups that lie in the plane of the paper, around each chiral carbon. Hydrogen atoms connected to wedge-and-dash bonds must be explicitly shown to reflect accurate stereochemistry.

**Interactive Component:**

The diagram provides tools to draw and modify molecular structures, including:
- Lines for drawing bonds.
- Wedges and dashes for stereochemistry.
- Options to add specific atoms such as carbon (C), hydrogen (H), and oxygen (O).

This precise depiction of molecular configurations is crucial for understanding the spatial arrangement and physical properties of the resultant alcohols.

By following this reaction path and noting stereochemistry, students gain insight into how structural changes occur in organic reactions, enhancing their understanding of molecular transformations.

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