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 8
![### Predicting the Products of Organic Reactions
**Problem Statement:**
Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.
**Reaction:**
\[ \text{H} \quad \text{H} \]
\[ \text{C} \equiv \text{C} + \text{CH}_2\text{I}_2 \rightarrow \quad \text{Zn(Cu), ether} \]
\[ \text{H}_3\text{C} \quad \text{CH}_3 \]
### Explanation:
**Reactants and Reagents:**
1. The starting molecule is 2-butyne with the molecular formula \( \text{C}_4\text{H}_6 \). The structure is as follows:
\[ \text{H}_3\text{C}-\text{C} \equiv \text{C}-\text{CH}_3 \]
2. The reaction involves methylene iodide (\(\text{CH}_2\text{I}_2\)) and zinc-copper couple (Zn/Cu) in ether as the solvent.
**Reaction Mechanism:**
1. The reaction shown is the Simmons-Smith reaction, which converts alkenes (or alkynes in some cases) into cyclopropane derivatives using a carbenoid intermediate.
2. Here, the methylene iodide reacts with the zinc-copper couple to form the carbenoid (iodozincmethylene), which then adds to the triple bond of the alkyne.
**Product:**
The product of this reaction is trans-2,3-dimethylcyclopropane.
- The cyclopropanation of the alkyne will result in the formation of a three-membered ring with two methyl groups attached to the newly formed cyclopropane ring. The product can be represented as:
\[ \text{H}_3\text{C}\text{-}\text{C}\text{-}\overset{\displaystyle\sf II}{\text{CH}_2} \text{-}\overset{-\displaystyle{\sf II}}{\text{C}}\text{-}\text{CH}_3 \]
**Regiochemistry and Stereochemistry:**
- The reaction maintains the stereochemistry of the starting alkyne if specificity is maintained.
- The formed cyclopropane ring will have the](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Ff71695ef-d0f4-4003-9f93-ae5ca95ceb18%2F94569264-b6ff-4bd0-8ce7-a8d52d372d3f%2Fy2tegbp_processed.jpeg&w=3840&q=75)
Transcribed Image Text:### Predicting the Products of Organic Reactions
**Problem Statement:**
Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.
**Reaction:**
\[ \text{H} \quad \text{H} \]
\[ \text{C} \equiv \text{C} + \text{CH}_2\text{I}_2 \rightarrow \quad \text{Zn(Cu), ether} \]
\[ \text{H}_3\text{C} \quad \text{CH}_3 \]
### Explanation:
**Reactants and Reagents:**
1. The starting molecule is 2-butyne with the molecular formula \( \text{C}_4\text{H}_6 \). The structure is as follows:
\[ \text{H}_3\text{C}-\text{C} \equiv \text{C}-\text{CH}_3 \]
2. The reaction involves methylene iodide (\(\text{CH}_2\text{I}_2\)) and zinc-copper couple (Zn/Cu) in ether as the solvent.
**Reaction Mechanism:**
1. The reaction shown is the Simmons-Smith reaction, which converts alkenes (or alkynes in some cases) into cyclopropane derivatives using a carbenoid intermediate.
2. Here, the methylene iodide reacts with the zinc-copper couple to form the carbenoid (iodozincmethylene), which then adds to the triple bond of the alkyne.
**Product:**
The product of this reaction is trans-2,3-dimethylcyclopropane.
- The cyclopropanation of the alkyne will result in the formation of a three-membered ring with two methyl groups attached to the newly formed cyclopropane ring. The product can be represented as:
\[ \text{H}_3\text{C}\text{-}\text{C}\text{-}\overset{\displaystyle\sf II}{\text{CH}_2} \text{-}\overset{-\displaystyle{\sf II}}{\text{C}}\text{-}\text{CH}_3 \]
**Regiochemistry and Stereochemistry:**
- The reaction maintains the stereochemistry of the starting alkyne if specificity is maintained.
- The formed cyclopropane ring will have the
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