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Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 15CTQ
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**Instructions:** 1. **Problem Statement:** - Draw the major product of this reaction. Ignore inorganic byproducts. 2. **Reaction Details:** - **Initial Structure:** Cyclopentanone - A five-membered ring with a ketone group (C=O) at the top position. - **Reagents:** 1. **LDA (Lithium Diisopropylamide), -78 °C** 2. **CH₃CH₂Br (Ethyl Bromide), 1 equivalent** 3. **Steps to Consider:** - LDA is a strong, non-nucleophilic base that will deprotonate the most acidic proton. - The reaction will occur at low temperature (-78 °C) to avoid side reactions. - The subsequent addition of ethyl bromide will likely result in an alkylation. 4. **Expected Reaction Outcome:** - The LDA will deprotonate the α-carbon adjacent to the carbonyl group in cyclopentanone. - The carbanion formed will then undergo a nucleophilic substitution reaction with ethyl bromide, resulting in an alkylated product. 5. **Final Task:** - Draw the major organic product formed from the alkylation of cyclopentanone using the above reagents. 6. **Note:** - Ensure to label the final drawing correctly, showcasing the new alkyl group and maintaining the correct stereochemistry if applicable.
Transcribed Image Text:**Instructions:** 1. **Problem Statement:** - Draw the major product of this reaction. Ignore inorganic byproducts. 2. **Reaction Details:** - **Initial Structure:** Cyclopentanone - A five-membered ring with a ketone group (C=O) at the top position. - **Reagents:** 1. **LDA (Lithium Diisopropylamide), -78 °C** 2. **CH₃CH₂Br (Ethyl Bromide), 1 equivalent** 3. **Steps to Consider:** - LDA is a strong, non-nucleophilic base that will deprotonate the most acidic proton. - The reaction will occur at low temperature (-78 °C) to avoid side reactions. - The subsequent addition of ethyl bromide will likely result in an alkylation. 4. **Expected Reaction Outcome:** - The LDA will deprotonate the α-carbon adjacent to the carbonyl group in cyclopentanone. - The carbanion formed will then undergo a nucleophilic substitution reaction with ethyl bromide, resulting in an alkylated product. 5. **Final Task:** - Draw the major organic product formed from the alkylation of cyclopentanone using the above reagents. 6. **Note:** - Ensure to label the final drawing correctly, showcasing the new alkyl group and maintaining the correct stereochemistry if applicable.
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