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Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. CH3 NaOCH2CH3 excess CH3CH2OH

Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. CH3 NaOCH2CH3 excess CH3CH2OH

Chemistry
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
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**Acyl Transfer Reaction: Tetrahedral Intermediate** **Reaction Description:** Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Your task is to draw the tetrahedral intermediate as it is first formed in the following reaction: - Reaction Scheme: - Cyclohexanone acetate ester (where the acetate group has a carbonyl bonded to an oxygen, which is then bonded to a cyclohexane ring and a methyl group) reacts with excess ethanol (CH₃CH₂OH) in the presence of sodium ethoxide (NaOCH₂CH₃). **Instructions:** - You do not have to consider stereochemistry. - Include all valence lone pairs in your answer. - Do not include counter-ions, e.g., Na⁺, I⁻, in your answer. - In cases where there is more than one answer, just draw one. **Diagram Explanation:** - The workspace provided includes drawing tools to help visualize and sketch the tetrahedral intermediate. The panel includes options for drawing various shapes and chemical bonds, and adding elements and lone pairs. The exercise primarily focuses on understanding the mechanism of acyl transfer reactions through the formation of a tetrahedral intermediate. The goal is to accurately depict the intermediate without taking stereochemistry into account, emphasizing the correct placement of lone pairs and bonds.
Transcribed Image Text:**Acyl Transfer Reaction: Tetrahedral Intermediate** **Reaction Description:** Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Your task is to draw the tetrahedral intermediate as it is first formed in the following reaction: - Reaction Scheme: - Cyclohexanone acetate ester (where the acetate group has a carbonyl bonded to an oxygen, which is then bonded to a cyclohexane ring and a methyl group) reacts with excess ethanol (CH₃CH₂OH) in the presence of sodium ethoxide (NaOCH₂CH₃). **Instructions:** - You do not have to consider stereochemistry. - Include all valence lone pairs in your answer. - Do not include counter-ions, e.g., Na⁺, I⁻, in your answer. - In cases where there is more than one answer, just draw one. **Diagram Explanation:** - The workspace provided includes drawing tools to help visualize and sketch the tetrahedral intermediate. The panel includes options for drawing various shapes and chemical bonds, and adding elements and lone pairs. The exercise primarily focuses on understanding the mechanism of acyl transfer reactions through the formation of a tetrahedral intermediate. The goal is to accurately depict the intermediate without taking stereochemistry into account, emphasizing the correct placement of lone pairs and bonds.
Title: Acyl Transfer Reaction - Tetrahedral Intermediate --- **Concept:** Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed through a tetrahedral intermediate. In the following reaction, identify and draw the tetrahedral intermediate as it is first formed. **Reaction:** ![Reaction](https://example.com/reaction) \[ \text{Cyclopropanone} + \text{Ethylamine} \rightarrow \] **Instructions:** - **Do not consider stereochemistry** in your drawing. - **Include all valence lone pairs** in your answer. - **Exclude counter-ions** such as \( \text{Na}^+ \) or \( \text{I}^- \). - If multiple structures are possible, **draw only one**. **Tools:** A diagram tool is available to sketch the intermediate. Tools include options for drawing bonds, lone pairs, and molecular shapes. Adjust your drawing as needed to match the expected intermediate structure. ![Diagram Tool Screenshot](https://example.com/diagram_tool_screenshot) **Navigation:** Buttons for navigating to the previous and next sections are available. Use these to continue with further related educational content or to review prior information. **Contact:** For additional guidance or questions, use the "Email Instructor" feature. **Save and Exit:** Remember to save your progress by clicking the "Save and Exit" button. ---
Transcribed Image Text:Title: Acyl Transfer Reaction - Tetrahedral Intermediate --- **Concept:** Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed through a tetrahedral intermediate. In the following reaction, identify and draw the tetrahedral intermediate as it is first formed. **Reaction:** ![Reaction](https://example.com/reaction) \[ \text{Cyclopropanone} + \text{Ethylamine} \rightarrow \] **Instructions:** - **Do not consider stereochemistry** in your drawing. - **Include all valence lone pairs** in your answer. - **Exclude counter-ions** such as \( \text{Na}^+ \) or \( \text{I}^- \). - If multiple structures are possible, **draw only one**. **Tools:** A diagram tool is available to sketch the intermediate. Tools include options for drawing bonds, lone pairs, and molecular shapes. Adjust your drawing as needed to match the expected intermediate structure. ![Diagram Tool Screenshot](https://example.com/diagram_tool_screenshot) **Navigation:** Buttons for navigating to the previous and next sections are available. Use these to continue with further related educational content or to review prior information. **Contact:** For additional guidance or questions, use the "Email Instructor" feature. **Save and Exit:** Remember to save your progress by clicking the "Save and Exit" button. ---
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