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8. Predict the major product of the following multistep syntheses: a. 1. mCPBA 2. (CuLi 3. DMSO, (COCI)2, -60 °C 4. Et3N

8. Predict the major product of the following multistep syntheses: a. 1. mCPBA 2. (CuLi 3. DMSO, (COCI)2, -60 °C 4. Et3N

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
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Multistep Synthesis Problem:** **Objective: Predict the major product of the following multistep syntheses:** **Starting Material:** - Cyclohexene **Reagents:** 1. mCPBA (meta-Chloroperoxybenzoic acid) 2. Vinyl cuprate (\[(CH\(_2\)=CH)CuLi]_2\]) 3. DMSO (Dimethyl sulfoxide), (COCl)\(_2\), at -60 °C 4. Et\(_3\)N (Triethylamine) **Product:** - The major product of this reaction sequence is a ketone featuring a cyclohexyl group and a three-carbon chain with an alkene (double bond) at the end, shown in red. **Explanation of Steps:** 1. **Epoxidation**: The starting cyclohexene undergoes epoxidation by mCPBA to form an epoxide. 2. **Nucleophilic Opening**: The vinyl cuprate opens the epoxide and attaches a vinyl group to the carbon. 3. **Swern Oxidation**: DMSO and (COCl)\(_2\) at -60 °C facilitate the conversion of the alcohol group to a ketone. 4. **Neutralization**: Triethylamine (Et\(_3\)N) neutralizes the reaction mixture.
Transcribed Image Text:**Multistep Synthesis Problem:** **Objective: Predict the major product of the following multistep syntheses:** **Starting Material:** - Cyclohexene **Reagents:** 1. mCPBA (meta-Chloroperoxybenzoic acid) 2. Vinyl cuprate (\[(CH\(_2\)=CH)CuLi]_2\]) 3. DMSO (Dimethyl sulfoxide), (COCl)\(_2\), at -60 °C 4. Et\(_3\)N (Triethylamine) **Product:** - The major product of this reaction sequence is a ketone featuring a cyclohexyl group and a three-carbon chain with an alkene (double bond) at the end, shown in red. **Explanation of Steps:** 1. **Epoxidation**: The starting cyclohexene undergoes epoxidation by mCPBA to form an epoxide. 2. **Nucleophilic Opening**: The vinyl cuprate opens the epoxide and attaches a vinyl group to the carbon. 3. **Swern Oxidation**: DMSO and (COCl)\(_2\) at -60 °C facilitate the conversion of the alcohol group to a ketone. 4. **Neutralization**: Triethylamine (Et\(_3\)N) neutralizes the reaction mixture.
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