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4. As shown below, compound 2 can be made from compound 1 in two steps. Provide the reagents, A, and draw the product B for the first step. Then, provide the reagents C that lead to the final product. (Hint: Product B has a peak in its 'H NMR spectrum at 11.1 ppm that integrates to 1H.) 1 OH A H₂₂ CrO4 Mg Br C B OH

4. As shown below, compound 2 can be made from compound 1 in two steps. Provide the reagents, A, and draw the product B for the first step. Then, provide the reagents C that lead to the final product. (Hint: Product B has a peak in its 'H NMR spectrum at 11.1 ppm that integrates to 1H.) 1 OH A H₂₂ CrO4 Mg Br C B OH

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
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I wanted to double check my synthesis. Especially if the grignard reaction would make sense as a way to add an ethyl group 

**Exercise 4: Organic Chemistry Reaction Pathway** This exercise involves converting compound 1 to compound 2 through a two-step reaction process. You are required to identify the reagents used in each step and draw the intermediate product, B, for the first step. **Compound 1:** Structure of compound 1 is shown as 3-hydroxybutane. **Step 1:** Reagent A: \( \text{H}_2\text{CrO}_4 \) (chromic acid) - **Action:** Oxidation - **Product B:** The resulting product from this oxidation step is 3-ketobutane. **Structure of Product B:** - The structure includes a butane chain where the hydroxyl group from compound 1 has been oxidized to a ketone, resulting in 3-oxobutanoic acid. **Step 2:** Reagent C: Ethylmagnesium bromide (\( \text{C}_2\text{H}_5\text{MgBr} \)) - **Action:** Grignard reaction followed by hydrolysis - **Final Product (Compound 2):** The final product is 4-pentyl-4-oxobutanoic acid. **Hints for Analysis:** - Product B has a significant peak in its \( ^1\text{H} \) NMR spectrum at 11.1 ppm, which integrates to 1H. This suggests the presence of an aldehyde or possibly carboxylic acid proton. **Reaction Pathway Summary:** 1. **Oxidation Step:** - \( \text{OH} \to \text{C}=\text{O} \) - Reagent: Chromic acid (\( \text{H}_2\text{CrO}_4 \)) - Intermediate: 3-oxobutanoic acid (Product B) 2. **Grignard Reaction:** - Addition of ethyl group (\( \text{CH}_3\text{CH}_2\text{MgBr} \)) - Followed by hydrolysis - Final Product: 4-pentyl-4-oxobutanoic acid (Compound 2) This transformative process demonstrates the utilization of oxidation and Grignard reaction techniques in organic synthesis to manipulate functional groups and extend carbon chains. The proper selection and application of reagents,
Transcribed Image Text:**Exercise 4: Organic Chemistry Reaction Pathway** This exercise involves converting compound 1 to compound 2 through a two-step reaction process. You are required to identify the reagents used in each step and draw the intermediate product, B, for the first step. **Compound 1:** Structure of compound 1 is shown as 3-hydroxybutane. **Step 1:** Reagent A: \( \text{H}_2\text{CrO}_4 \) (chromic acid) - **Action:** Oxidation - **Product B:** The resulting product from this oxidation step is 3-ketobutane. **Structure of Product B:** - The structure includes a butane chain where the hydroxyl group from compound 1 has been oxidized to a ketone, resulting in 3-oxobutanoic acid. **Step 2:** Reagent C: Ethylmagnesium bromide (\( \text{C}_2\text{H}_5\text{MgBr} \)) - **Action:** Grignard reaction followed by hydrolysis - **Final Product (Compound 2):** The final product is 4-pentyl-4-oxobutanoic acid. **Hints for Analysis:** - Product B has a significant peak in its \( ^1\text{H} \) NMR spectrum at 11.1 ppm, which integrates to 1H. This suggests the presence of an aldehyde or possibly carboxylic acid proton. **Reaction Pathway Summary:** 1. **Oxidation Step:** - \( \text{OH} \to \text{C}=\text{O} \) - Reagent: Chromic acid (\( \text{H}_2\text{CrO}_4 \)) - Intermediate: 3-oxobutanoic acid (Product B) 2. **Grignard Reaction:** - Addition of ethyl group (\( \text{CH}_3\text{CH}_2\text{MgBr} \)) - Followed by hydrolysis - Final Product: 4-pentyl-4-oxobutanoic acid (Compound 2) This transformative process demonstrates the utilization of oxidation and Grignard reaction techniques in organic synthesis to manipulate functional groups and extend carbon chains. The proper selection and application of reagents,
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