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What is the expected major product of the following reaction sequence? da O 1. t-BuOK, t-BuOH 2a. 03, CH₂Cl₂ 2b. Me₂S que -ОН -OH L..OH "OH OTH HÅH н + enantiomer

What is the expected major product of the following reaction sequence? da O 1. t-BuOK, t-BuOH 2a. 03, CH₂Cl₂ 2b. Me₂S que -ОН -OH L..OH "OH OTH HÅH н + enantiomer

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Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Question 44
**Question:** What is the expected *major* product of the following reaction sequence? The chemical equation shown displays a cyclohexane ring with a chlorine atom attached (cyclohexyl chloride). This compound undergoes two reaction steps: 1. The first step involves treatment with t-BuOK (tert-butoxide) and t-BuOH (tert-butyl alcohol). 2. The second step, denoted as 2a and 2b, involves ozonolysis using ozone (O₃), CH₂Cl₂ (dichloromethane) followed by dimethyl sulfide (Me₂S). **Options:** - **Option 1:** A linear chain with six carbon atoms, an aldehyde group (–CHO) at the terminal carbon, and a ketone group (–C=O) at the fifth carbon. - **Option 2:** A linear chain with five carbon atoms, a terminal aldehyde group (–CHO), and another aldehyde group (–CHO) on the other end, separated by three carbons. - **Option 3:** A cyclohexane ring with a ketone group (–C=O) at one carbon and an aldehyde group (–CHO) at the adjacent carbon. - **Option 4:** A cyclohexane ring with two hydroxyl groups (–OH) on adjacent carbons. - **Option 5:** A cyclohexane ring with two hydroxyl groups (–OH) on adjacent carbons, but indicated as enantiomers (mirror-image isomers). **Explanation of Reactions:** Step 1: The t-BuOK and t-BuOH would dehydrohalogenate the cyclohexyl chloride to form a cyclohexene through an E2 elimination reaction. Step 2: Ozonolysis of cyclohexene would cleave the double bond and yield products bearing carbonyl groups (ketones or aldehydes). The correct option should represent the compounds resulting from these reactions.
Transcribed Image Text:**Question:** What is the expected *major* product of the following reaction sequence? The chemical equation shown displays a cyclohexane ring with a chlorine atom attached (cyclohexyl chloride). This compound undergoes two reaction steps: 1. The first step involves treatment with t-BuOK (tert-butoxide) and t-BuOH (tert-butyl alcohol). 2. The second step, denoted as 2a and 2b, involves ozonolysis using ozone (O₃), CH₂Cl₂ (dichloromethane) followed by dimethyl sulfide (Me₂S). **Options:** - **Option 1:** A linear chain with six carbon atoms, an aldehyde group (–CHO) at the terminal carbon, and a ketone group (–C=O) at the fifth carbon. - **Option 2:** A linear chain with five carbon atoms, a terminal aldehyde group (–CHO), and another aldehyde group (–CHO) on the other end, separated by three carbons. - **Option 3:** A cyclohexane ring with a ketone group (–C=O) at one carbon and an aldehyde group (–CHO) at the adjacent carbon. - **Option 4:** A cyclohexane ring with two hydroxyl groups (–OH) on adjacent carbons. - **Option 5:** A cyclohexane ring with two hydroxyl groups (–OH) on adjacent carbons, but indicated as enantiomers (mirror-image isomers). **Explanation of Reactions:** Step 1: The t-BuOK and t-BuOH would dehydrohalogenate the cyclohexyl chloride to form a cyclohexene through an E2 elimination reaction. Step 2: Ozonolysis of cyclohexene would cleave the double bond and yield products bearing carbonyl groups (ketones or aldehydes). The correct option should represent the compounds resulting from these reactions.
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