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The sugar methyl B-D-glucopyranoside converts rapidly to the open chain aldehyde under acidic conditions, through the same mechanism as acetal hydrolysis. Draw a complete, detailed mechanism of this transformation. НО НО- но Но H3O+ НО, ОН ОН О ОН ОН H + HO-CH3

The sugar methyl B-D-glucopyranoside converts rapidly to the open chain aldehyde under acidic conditions, through the same mechanism as acetal hydrolysis. Draw a complete, detailed mechanism of this transformation. НО НО- но Но H3O+ НО, ОН ОН О ОН ОН H + HO-CH3

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**Title**: Conversion of Methyl β-D-Glucopyranoside to Open Chain Aldehyde **Description**: The sugar methyl β-D-glucopyranoside converts rapidly to the open chain aldehyde under acidic conditions, through the same mechanism as acetal hydrolysis. A complete, detailed mechanism of this transformation should be drawn. **Chemical Reaction**: 1. **Reactant**: Methyl β-D-glucopyranoside - Structure: A cyclic compound with glucose structure, several hydroxyl groups (HO) attached, and an O-CH₃ group as part of the acetal linkage. 2. **Condition**: The reaction takes place in the presence of hydronium ion (H₃O⁺), which facilitates the conversion. 3. **Products**: - An open chain form of glucose, with an aldehyde group (terminal carbon has a double-bonded oxygen, O and a hydrogen, H). - Methanol (HO-CH₃) as a by-product. **Process**: - The reaction involves the breaking of the ether linkage (O-CH₃) in the cyclic sugar molecule, leading to its conversion into an open chain form. - The open chain structure shows the aldehyde group and several hydroxyl groups remaining intact, illustrating the reformation of glucose’s linear structure. **Diagram Explanation**: - The reaction starts with a representation of the cyclic sugar with labeled hydroxyl groups and an ether linkage. - An arrow, labeled H₃O⁺, indicates the catalytic role of acidic conditions. - The final structures show an open chain sugar molecule and a methanol molecule as the reaction products. **Learning Objective**: Understand the acid-catalyzed conversion of sugar acetals to open chain aldehydes, illustrating the chemical transformation involving the breakdown of cyclic forms to their linear counterparts. This reaction mimics acetal hydrolysis, showcasing carbohydrate chemistry dynamics.
Transcribed Image Text:**Title**: Conversion of Methyl β-D-Glucopyranoside to Open Chain Aldehyde **Description**: The sugar methyl β-D-glucopyranoside converts rapidly to the open chain aldehyde under acidic conditions, through the same mechanism as acetal hydrolysis. A complete, detailed mechanism of this transformation should be drawn. **Chemical Reaction**: 1. **Reactant**: Methyl β-D-glucopyranoside - Structure: A cyclic compound with glucose structure, several hydroxyl groups (HO) attached, and an O-CH₃ group as part of the acetal linkage. 2. **Condition**: The reaction takes place in the presence of hydronium ion (H₃O⁺), which facilitates the conversion. 3. **Products**: - An open chain form of glucose, with an aldehyde group (terminal carbon has a double-bonded oxygen, O and a hydrogen, H). - Methanol (HO-CH₃) as a by-product. **Process**: - The reaction involves the breaking of the ether linkage (O-CH₃) in the cyclic sugar molecule, leading to its conversion into an open chain form. - The open chain structure shows the aldehyde group and several hydroxyl groups remaining intact, illustrating the reformation of glucose’s linear structure. **Diagram Explanation**: - The reaction starts with a representation of the cyclic sugar with labeled hydroxyl groups and an ether linkage. - An arrow, labeled H₃O⁺, indicates the catalytic role of acidic conditions. - The final structures show an open chain sugar molecule and a methanol molecule as the reaction products. **Learning Objective**: Understand the acid-catalyzed conversion of sugar acetals to open chain aldehydes, illustrating the chemical transformation involving the breakdown of cyclic forms to their linear counterparts. This reaction mimics acetal hydrolysis, showcasing carbohydrate chemistry dynamics.
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