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HO CH3 HO HO 1L но HO OMe 2. HO Proton Transfer но HO. HO. HO CH3OH, H* HO curved-arrow mechanism for this transformation: 1. When glucose is treated with methanol and acid, the methyl glucoside is formed. Provide a complete HO, но Carbohydrates

HO CH3 HO HO 1L но HO OMe 2. HO Proton Transfer но HO. HO. HO CH3OH, H* HO curved-arrow mechanism for this transformation: 1. When glucose is treated with methanol and acid, the methyl glucoside is formed. Provide a complete HO, но Carbohydrates

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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Could you please check if this is right and elaborate the mechanism?
### Carbohydrates #### 1. Mechanism for Methyl Glucoside Formation from Glucose and Methanol When glucose is treated with methanol and acid, the methyl glucoside is formed. Below is the complete curved-arrow mechanism for this transformation: 1. **Starting Compound (Glucose)**: - The structure is a glucose molecule with hydroxyl (-OH) groups attached to carbon atoms 2, 3, 4, and 6. An ether group (-OCH3) is attached to carbon atom 1, forming a hemiacetal structure. 2. **Step 1: Protonation of the Hydroxyl Group**: - The hydroxyl group on the first carbon is protonated by H⁺ (acid), facilitating the conversion of the -OH to a better leaving group. 3. **Step 2: Loss of Water (Elimination)**: - The protonated hydroxyl group (now a water molecule, H₂O) leaves, forming a carbocation on the first carbon. 4. **Step 3: Nucleophilic Attack by Methanol**: - Methanol (CH₃OH) acts as a nucleophile and attacks the carbocation on the first carbon. This involves a curved arrow showing lone pair electrons from the oxygen in methanol attacking the carbocation. 5. **Step 4: Proton Transfer**: - A proton (H⁺) transfers from the oxygen in the -OCH₃ group, resulting in the final product, methyl glucoside. 6. **Final Product (Methyl Glucoside)**: - The final product is a cyclic molecule where a methoxy group (-OCH₃) is attached to the first carbon, and hydroxyl groups are attached to the 2nd, 3rd, 4th, and 6th carbons respectively. ### Detailed Explanation of the Diagrams: - **Left Diagram (Steps 1 & 2)**: - Shows the initial protonation of the hydroxyl group on carbon 1 and the subsequent loss of a water molecule. - The arrow from the hydrogen to the hydroxyl group indicates protonation, and the arrow from the oxygen in the leaving water molecule indicates elimination. - **Right Diagram (Steps 3 & 4)**: - Demonstrates the nucleophilic attack by methanol and the proton transfer process. - Arrows depict
Transcribed Image Text:### Carbohydrates #### 1. Mechanism for Methyl Glucoside Formation from Glucose and Methanol When glucose is treated with methanol and acid, the methyl glucoside is formed. Below is the complete curved-arrow mechanism for this transformation: 1. **Starting Compound (Glucose)**: - The structure is a glucose molecule with hydroxyl (-OH) groups attached to carbon atoms 2, 3, 4, and 6. An ether group (-OCH3) is attached to carbon atom 1, forming a hemiacetal structure. 2. **Step 1: Protonation of the Hydroxyl Group**: - The hydroxyl group on the first carbon is protonated by H⁺ (acid), facilitating the conversion of the -OH to a better leaving group. 3. **Step 2: Loss of Water (Elimination)**: - The protonated hydroxyl group (now a water molecule, H₂O) leaves, forming a carbocation on the first carbon. 4. **Step 3: Nucleophilic Attack by Methanol**: - Methanol (CH₃OH) acts as a nucleophile and attacks the carbocation on the first carbon. This involves a curved arrow showing lone pair electrons from the oxygen in methanol attacking the carbocation. 5. **Step 4: Proton Transfer**: - A proton (H⁺) transfers from the oxygen in the -OCH₃ group, resulting in the final product, methyl glucoside. 6. **Final Product (Methyl Glucoside)**: - The final product is a cyclic molecule where a methoxy group (-OCH₃) is attached to the first carbon, and hydroxyl groups are attached to the 2nd, 3rd, 4th, and 6th carbons respectively. ### Detailed Explanation of the Diagrams: - **Left Diagram (Steps 1 & 2)**: - Shows the initial protonation of the hydroxyl group on carbon 1 and the subsequent loss of a water molecule. - The arrow from the hydrogen to the hydroxyl group indicates protonation, and the arrow from the oxygen in the leaving water molecule indicates elimination. - **Right Diagram (Steps 3 & 4)**: - Demonstrates the nucleophilic attack by methanol and the proton transfer process. - Arrows depict
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