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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![**Title: Assessing the Major Product of a Given Organic Reaction**
**Introduction:**
In organic chemistry, predicting the major product of a chemical reaction is crucial for understanding reaction mechanisms and outcomes. The given problem involves a cyclopentanone reacting in the presence of LDA followed by the addition of an ethyl acetate molecule. The steps and anticipated products are evaluated below.
**Reaction Details:**
**1. Reactants:**
- **Cyclopentanone:** A five-membered ring ketone (\(\displaystyle\text{C}_5\text{H}_8\text{O}\)).
- **Lithium Diisopropylamide (LDA):** A strong, non-nucleophilic base.
- **Ethyl acetate:** An ester (\(\displaystyle\text{C}_4\text{H}_8\text{O}_2\)).
**2. Reaction Steps:**
**Step 1:**
- **Deprotonation with LDA:** LDA abstracts a proton (usually the alpha hydrogen) from cyclopentanone, creating a highly reactive enolate ion. This enolate is represented as:
\[
\begin{aligned}
&\text{Cyclopentanone} \xrightarrow{\text{1) LDA}} \text{Cyclopentanone enolate} \\
\end{aligned}
\]
**Step 2:**
- **Nucleophilic Attack on Ethyl Acetate:** The enolate ion then attacks the carbon of the carbonyl group in ethyl acetate. This step leads to the formation of a new carbon-carbon bond, corresponding to a nucleophilic acyl substitution.
\[
\begin{aligned}
&\text{Cyclopentanone enolate} + \text{Ethyl acetate} \xrightarrow{\text{reaction}} \text{Product}
\end{aligned}
\]
**3. Structure Examination:**
- **Final Product:**
The resultant product will have the new carbon at the alpha position of cyclopentanone bonded to the carbonyl carbon of ethyl acetate. Thus, the major product forms a β-dicarbonyl compound.
**Explanation with Diagrams:**
Diagrams should illustrate:
- **Initial Structure:** Cyclopentanone and ethyl acetate should be distinct.
- **Intermediates:** Demonstrate the formation of](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fb6c48281-bcf8-4d84-ad3c-d8fb9e0661f0%2Fcd0f368b-a687-4177-8b0c-f6cb771e4ec5%2F0r10s_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Title: Assessing the Major Product of a Given Organic Reaction**
**Introduction:**
In organic chemistry, predicting the major product of a chemical reaction is crucial for understanding reaction mechanisms and outcomes. The given problem involves a cyclopentanone reacting in the presence of LDA followed by the addition of an ethyl acetate molecule. The steps and anticipated products are evaluated below.
**Reaction Details:**
**1. Reactants:**
- **Cyclopentanone:** A five-membered ring ketone (\(\displaystyle\text{C}_5\text{H}_8\text{O}\)).
- **Lithium Diisopropylamide (LDA):** A strong, non-nucleophilic base.
- **Ethyl acetate:** An ester (\(\displaystyle\text{C}_4\text{H}_8\text{O}_2\)).
**2. Reaction Steps:**
**Step 1:**
- **Deprotonation with LDA:** LDA abstracts a proton (usually the alpha hydrogen) from cyclopentanone, creating a highly reactive enolate ion. This enolate is represented as:
\[
\begin{aligned}
&\text{Cyclopentanone} \xrightarrow{\text{1) LDA}} \text{Cyclopentanone enolate} \\
\end{aligned}
\]
**Step 2:**
- **Nucleophilic Attack on Ethyl Acetate:** The enolate ion then attacks the carbon of the carbonyl group in ethyl acetate. This step leads to the formation of a new carbon-carbon bond, corresponding to a nucleophilic acyl substitution.
\[
\begin{aligned}
&\text{Cyclopentanone enolate} + \text{Ethyl acetate} \xrightarrow{\text{reaction}} \text{Product}
\end{aligned}
\]
**3. Structure Examination:**
- **Final Product:**
The resultant product will have the new carbon at the alpha position of cyclopentanone bonded to the carbonyl carbon of ethyl acetate. Thus, the major product forms a β-dicarbonyl compound.
**Explanation with Diagrams:**
Diagrams should illustrate:
- **Initial Structure:** Cyclopentanone and ethyl acetate should be distinct.
- **Intermediates:** Demonstrate the formation of
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