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Draw the product of the reaction shown below. Use wedge and dash bonds to indicate relative stereochemistry where appropriate. Ignore inorganic byproducts. OsO4 (catalytic) NMO Q

Draw the product of the reaction shown below. Use wedge and dash bonds to indicate relative stereochemistry where appropriate. Ignore inorganic byproducts. OsO4 (catalytic) NMO Q

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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**Understanding the Reaction and Drawing the Product** **Objective:** Draw the product of the reaction shown below. Use wedge and dash bonds to indicate relative stereochemistry where appropriate. Ignore inorganic byproducts. **Reactant:** - The reactant molecule is a hexagon with a double bond indicating a cyclohexene derivative. - There is a single bond attached with a solid wedge, indicating a substituent projecting out of the plane of the ring. **Reaction Conditions:** - **OsO4 (catalytic)**: Osmium tetroxide in catalytic amounts. - **NMO**: N-Methylmorpholine N-oxide, often used along with OsO4 for dihydroxylation reactions. **Expected Transformation:** The OsO4/NMO combination typically leads to the dihydroxylation of alkenes, converting the double bond into a glycol (vicinal diol). This reaction should result in the syn addition of two hydroxyl groups across the double bond, maintaining the stereochemistry indicated by the solid wedge bond. **Step-by-Step Explanation:** 1. **Starting Material:** - Cyclohexene derivative with a substituent indicated by a solid wedge. 2. **Oxidation Reaction:** - The alkene reacts with OsO4/NMO resulting in the formation of a cis-diol (hydroxyl groups added syn to the same side). **Graphical Representation:** ![Cyclohexene Reactant](image) **Reagents:** - OsO4 (catalytic) - NMO **Reaction Outcome:** - Formation of a cis-1,2-diol product from the cyclohexene derivative. **Note:** In drawing the product, ensure that wedge and dash bonds are utilized to indicate the stereochemistry of the vicinal diol formed. The hydroxyl groups (-OH) will be added to the carbons of the original double bond. --- This reaction is crucial in organic synthesis for the stereospecific formation of diols from alkenes, facilitating the understanding of stereochemistry in cyclic compounds.
Transcribed Image Text:**Understanding the Reaction and Drawing the Product** **Objective:** Draw the product of the reaction shown below. Use wedge and dash bonds to indicate relative stereochemistry where appropriate. Ignore inorganic byproducts. **Reactant:** - The reactant molecule is a hexagon with a double bond indicating a cyclohexene derivative. - There is a single bond attached with a solid wedge, indicating a substituent projecting out of the plane of the ring. **Reaction Conditions:** - **OsO4 (catalytic)**: Osmium tetroxide in catalytic amounts. - **NMO**: N-Methylmorpholine N-oxide, often used along with OsO4 for dihydroxylation reactions. **Expected Transformation:** The OsO4/NMO combination typically leads to the dihydroxylation of alkenes, converting the double bond into a glycol (vicinal diol). This reaction should result in the syn addition of two hydroxyl groups across the double bond, maintaining the stereochemistry indicated by the solid wedge bond. **Step-by-Step Explanation:** 1. **Starting Material:** - Cyclohexene derivative with a substituent indicated by a solid wedge. 2. **Oxidation Reaction:** - The alkene reacts with OsO4/NMO resulting in the formation of a cis-diol (hydroxyl groups added syn to the same side). **Graphical Representation:** ![Cyclohexene Reactant](image) **Reagents:** - OsO4 (catalytic) - NMO **Reaction Outcome:** - Formation of a cis-1,2-diol product from the cyclohexene derivative. **Note:** In drawing the product, ensure that wedge and dash bonds are utilized to indicate the stereochemistry of the vicinal diol formed. The hydroxyl groups (-OH) will be added to the carbons of the original double bond. --- This reaction is crucial in organic synthesis for the stereospecific formation of diols from alkenes, facilitating the understanding of stereochemistry in cyclic compounds.
### Chemical Reaction and Product Drawing Exercise #### Problem Statement: Draw the product of the reaction shown below. Ignore inorganic byproducts. ![Chemical Structure](https://via.placeholder.com/150) \[OH\] #### Reagents: - PCC (Pyridinium chlorochromate) - \( \text{CH}_2\text{Cl}_2 \) (Dichloromethane) #### Instructions: 1. Examine the chemical structure provided. 2. Using PCC and \( \text{CH}_2\text{Cl}_2 \) as reagents, predict the product of the reaction by applying your knowledge of organic chemistry mechanisms. 3. Draw the predicted product in the designated area below. #### Diagram Key: - **Structure Shown**: A benzene ring with an adjoining hydroxyl group (OH) and a fused six-membered ring structure. - **Reagents Passage (Arrow)**: Indicates the transformation of the initial structure into the product upon the addition of the reagents PCC and \( \text{CH}_2\text{Cl}_2 \). #### Reaction Explanation: Pyridinium chlorochromate (PCC) is commonly used as an oxidizing agent. When an alcohol such as the one presented in the structure is treated with PCC in an organic solvent like dichloromethane (\( \text{CH}_2\text{Cl}_2 \)), it typically converts primary alcohols into aldehydes and secondary alcohols into ketones. #### Drawing Area: Use the provided interactive tool below to draw the product of the reaction. This tool will help solidify your understanding of the oxidation process facilitated by PCC. **Interactive Drawing Tool**: [Select to Draw] --- We hope this exercise helps you better understand organic reaction mechanisms involving oxidation by PCC.
Transcribed Image Text:### Chemical Reaction and Product Drawing Exercise #### Problem Statement: Draw the product of the reaction shown below. Ignore inorganic byproducts. ![Chemical Structure](https://via.placeholder.com/150) \[OH\] #### Reagents: - PCC (Pyridinium chlorochromate) - \( \text{CH}_2\text{Cl}_2 \) (Dichloromethane) #### Instructions: 1. Examine the chemical structure provided. 2. Using PCC and \( \text{CH}_2\text{Cl}_2 \) as reagents, predict the product of the reaction by applying your knowledge of organic chemistry mechanisms. 3. Draw the predicted product in the designated area below. #### Diagram Key: - **Structure Shown**: A benzene ring with an adjoining hydroxyl group (OH) and a fused six-membered ring structure. - **Reagents Passage (Arrow)**: Indicates the transformation of the initial structure into the product upon the addition of the reagents PCC and \( \text{CH}_2\text{Cl}_2 \). #### Reaction Explanation: Pyridinium chlorochromate (PCC) is commonly used as an oxidizing agent. When an alcohol such as the one presented in the structure is treated with PCC in an organic solvent like dichloromethane (\( \text{CH}_2\text{Cl}_2 \)), it typically converts primary alcohols into aldehydes and secondary alcohols into ketones. #### Drawing Area: Use the provided interactive tool below to draw the product of the reaction. This tool will help solidify your understanding of the oxidation process facilitated by PCC. **Interactive Drawing Tool**: [Select to Draw] --- We hope this exercise helps you better understand organic reaction mechanisms involving oxidation by PCC.
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