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: Understanding Hydroboration-Oxidation Reactions**
**Question:**
What is the major product of the following reaction?
**Reactants:**
1. \( \text{BH}_3 \cdot \text{THF} \)
2. \( \text{NaOH}, \text{H}_2\text{O}_2, \text{H}_2\text{O} \)
**Structure of the Alkyne:**
The starting material is a terminal alkyne with the following structure:
\[
\begin{array}{c}
\text{C}\equiv\text{C} - \text{CH}_3 \\
\vert \\
\text{C}
\end{array}
\]
**Reaction Description:**
This reaction is a typical hydroboration-oxidation process, which converts alkynes into alcohols. It involves two main steps:
1. **Hydroboration:** A borane reagent (BH\(_3\) – THF complex) adds across the triple bond of the alkyne, forming an alkylborane intermediate.
2. **Oxidation:** The alkylborane intermediate is oxidized using hydrogen peroxide in the presence of a base (NaOH), resulting in the formation of an alcohol.
**Product Options:**
1. **Option A:**
\[
\begin{array}{c}
\text{OH} \\
\vert \\
\text{C} = \text{C} - \text{CH}_3 \\
\vert \\
\text{H}
\end{array}
\]
2. **Option B:**
\[
\begin{array}{c}
\text{H} \\
\vert \\
\text{C} = \text{C} - \text{CH}_3 \\
\vert \\
\text{OH}
\end{array}
\]
3. **Option C:**
(Not shown in the image)
**Explanation:**
In hydroboration-oxidation of alkynes, the addition of BH\(_3\) occurs in an anti-Markovnikov fashion, and the result after oxidation is an aldehyde for a terminal alkyne. However, the structure of the drawn options A and B suggests alcohol products rather than](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fd1272796-fc0f-416a-81a3-03a4c523ec88%2F85d7bde9-fb28-436c-82b6-626ed63152be%2F1itd84q_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Title: Understanding Hydroboration-Oxidation Reactions**
**Question:**
What is the major product of the following reaction?
**Reactants:**
1. \( \text{BH}_3 \cdot \text{THF} \)
2. \( \text{NaOH}, \text{H}_2\text{O}_2, \text{H}_2\text{O} \)
**Structure of the Alkyne:**
The starting material is a terminal alkyne with the following structure:
\[
\begin{array}{c}
\text{C}\equiv\text{C} - \text{CH}_3 \\
\vert \\
\text{C}
\end{array}
\]
**Reaction Description:**
This reaction is a typical hydroboration-oxidation process, which converts alkynes into alcohols. It involves two main steps:
1. **Hydroboration:** A borane reagent (BH\(_3\) – THF complex) adds across the triple bond of the alkyne, forming an alkylborane intermediate.
2. **Oxidation:** The alkylborane intermediate is oxidized using hydrogen peroxide in the presence of a base (NaOH), resulting in the formation of an alcohol.
**Product Options:**
1. **Option A:**
\[
\begin{array}{c}
\text{OH} \\
\vert \\
\text{C} = \text{C} - \text{CH}_3 \\
\vert \\
\text{H}
\end{array}
\]
2. **Option B:**
\[
\begin{array}{c}
\text{H} \\
\vert \\
\text{C} = \text{C} - \text{CH}_3 \\
\vert \\
\text{OH}
\end{array}
\]
3. **Option C:**
(Not shown in the image)
**Explanation:**
In hydroboration-oxidation of alkynes, the addition of BH\(_3\) occurs in an anti-Markovnikov fashion, and the result after oxidation is an aldehyde for a terminal alkyne. However, the structure of the drawn options A and B suggests alcohol products rather than
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