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 10
![**Exercise: Predicting Reaction Products**
---
**Task:**
Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.
**Reaction:**
\[ \text{Reactant:} \]
(The reactant is a compound containing a double bond between a carbon atom bonded to a methyl group (CH₃) and another carbon atom.)
\[
\begin{array}{c}
1. \text{Hg(OAc)}_2, \text{H}_2\text{O} \\
2. \text{NaBH}_4
\end{array}
\]
---
**Explanation:**
The provided reaction involves the addition of mercuric acetate (Hg(OAc)₂) in the presence of water (H₂O), followed by reduction with sodium borohydride (NaBH₄). This is a common method for converting alkenes into alcohols, specifically known as oxymercuration-demercuration.
1. **Oxymercuration**: The double bond reacts with mercuric acetate and water to form a mercurinium ion intermediate. This intermediate then undergoes nucleophilic attack by water, leading to the formation of an organomercury compound.
2. **Demercuration**: The organomercury compound is then reduced by sodium borohydride (NaBH₄), replacing the mercury with a hydrogen atom, resulting in the formation of an alcohol.
**Product:**
The product of this reaction will be an alcohol where the hydroxyl group (OH) is added to the more substituted carbon in the double bond, following Markovnikov's rule.
**Regiochemistry:**
The reaction adheres to Markovnikov’s rule, where the hydroxyl group attaches to the more substituted carbon atom of the original double bond.
**Stereochemistry:**
The resulting product does not have stereochemical constraints as the addition of Hg(OAc)₂ and the subsequent reduction with NaBH₄ typically lead to racemic mixtures if stereocenters are formed.
End of Exercise.
---
This explanation provides students with a clear understanding of the reaction process, the intermediate steps, and the resulting products, emphasizing the importance of regiochemistry and stereochemistry in organic synthesis.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Ff71695ef-d0f4-4003-9f93-ae5ca95ceb18%2F9e94b30c-8a0b-4f0b-b451-3817ddc5eb58%2Foa82ivn_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Exercise: Predicting Reaction Products**
---
**Task:**
Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.
**Reaction:**
\[ \text{Reactant:} \]
(The reactant is a compound containing a double bond between a carbon atom bonded to a methyl group (CH₃) and another carbon atom.)
\[
\begin{array}{c}
1. \text{Hg(OAc)}_2, \text{H}_2\text{O} \\
2. \text{NaBH}_4
\end{array}
\]
---
**Explanation:**
The provided reaction involves the addition of mercuric acetate (Hg(OAc)₂) in the presence of water (H₂O), followed by reduction with sodium borohydride (NaBH₄). This is a common method for converting alkenes into alcohols, specifically known as oxymercuration-demercuration.
1. **Oxymercuration**: The double bond reacts with mercuric acetate and water to form a mercurinium ion intermediate. This intermediate then undergoes nucleophilic attack by water, leading to the formation of an organomercury compound.
2. **Demercuration**: The organomercury compound is then reduced by sodium borohydride (NaBH₄), replacing the mercury with a hydrogen atom, resulting in the formation of an alcohol.
**Product:**
The product of this reaction will be an alcohol where the hydroxyl group (OH) is added to the more substituted carbon in the double bond, following Markovnikov's rule.
**Regiochemistry:**
The reaction adheres to Markovnikov’s rule, where the hydroxyl group attaches to the more substituted carbon atom of the original double bond.
**Stereochemistry:**
The resulting product does not have stereochemical constraints as the addition of Hg(OAc)₂ and the subsequent reduction with NaBH₄ typically lead to racemic mixtures if stereocenters are formed.
End of Exercise.
---
This explanation provides students with a clear understanding of the reaction process, the intermediate steps, and the resulting products, emphasizing the importance of regiochemistry and stereochemistry in organic synthesis.
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