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What is the expected major product of the reaction sequence shown? Assume standard workup after each step and that only the major product of the first step is taken on to the second step. OH 1. PB13 2. NaOEt, EtOH

What is the expected major product of the reaction sequence shown? Assume standard workup after each step and that only the major product of the first step is taken on to the second step. OH 1. PB13 2. NaOEt, EtOH

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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**Question on Reaction Sequence** **Objective:** Determine the expected major product of the two-step reaction sequence shown. Standard workup is assumed after each step, and only the major product of the first step proceeds to the second step. **Reaction Steps:** 1. **Reagents:** - **Step 1:** PBr₃ (Phosphorus tribromide) - **Step 2:** NaOEt, EtOH (Sodium ethoxide in ethanol) **Starting Compound:** A cyclohexane ring with an attached hydroxyl group (OH) and a methyl group (CH₃) on the same carbon, represented in a wedge form indicating stereochemistry. --- **Multiple Choice Options:** 1. **Option 1:** A cyclohexene with an ethyl group extending in a wedge conformation. 2. **Option 2:** A cyclohexane with an ethyl group batched to the main structure. The methyl group is intact, in a wedge conformation. 3. **Option 3:** A cyclohexane with a bromine atom in a wedge and a methyl group in a similar spatial arrangement. 4. **Option 4:** A cyclohexane with an ethoxy group (OEt) in a wedge and the methyl group also in a wedge. **Analysis of Reaction Sequence:** 1. **First Step with PBr₃:** - Converts the alcohol group (OH) to a bromide (Br), maintaining the stereochemistry (suggested by the products' consistent wedge notation). 2. **Second Step with NaOEt, EtOH:** - Likely involves elimination, leading to a double bond formation. This sequence ultimately requires examining the potential transformations through substitution and elimination processes, leading to the final expected major product.
Transcribed Image Text:**Question on Reaction Sequence** **Objective:** Determine the expected major product of the two-step reaction sequence shown. Standard workup is assumed after each step, and only the major product of the first step proceeds to the second step. **Reaction Steps:** 1. **Reagents:** - **Step 1:** PBr₃ (Phosphorus tribromide) - **Step 2:** NaOEt, EtOH (Sodium ethoxide in ethanol) **Starting Compound:** A cyclohexane ring with an attached hydroxyl group (OH) and a methyl group (CH₃) on the same carbon, represented in a wedge form indicating stereochemistry. --- **Multiple Choice Options:** 1. **Option 1:** A cyclohexene with an ethyl group extending in a wedge conformation. 2. **Option 2:** A cyclohexane with an ethyl group batched to the main structure. The methyl group is intact, in a wedge conformation. 3. **Option 3:** A cyclohexane with a bromine atom in a wedge and a methyl group in a similar spatial arrangement. 4. **Option 4:** A cyclohexane with an ethoxy group (OEt) in a wedge and the methyl group also in a wedge. **Analysis of Reaction Sequence:** 1. **First Step with PBr₃:** - Converts the alcohol group (OH) to a bromide (Br), maintaining the stereochemistry (suggested by the products' consistent wedge notation). 2. **Second Step with NaOEt, EtOH:** - Likely involves elimination, leading to a double bond formation. This sequence ultimately requires examining the potential transformations through substitution and elimination processes, leading to the final expected major product.
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