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The following compound will undergo an intramolecular Heck reaction to give a single product with two chiral centers. This process is observed to occur diastereoselectively (a new chiral center is formed, but only one stereoisomer is obtained). Draw the product and rationalize the source of the observed diastereoselectivity: Jo Pd(OAc)2 ? PPh Et₂N Practice Problem 23.49a. Draw the product of the reaction. Include stereochemistry in your answer. Draw Your Solution

The following compound will undergo an intramolecular Heck reaction to give a single product with two chiral centers. This process is observed to occur diastereoselectively (a new chiral center is formed, but only one stereoisomer is obtained). Draw the product and rationalize the source of the observed diastereoselectivity: Jo Pd(OAc)2 ? PPh Et₂N Practice Problem 23.49a. Draw the product of the reaction. Include stereochemistry in your answer. Draw Your Solution

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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### Explanation of Intramolecular Heck Reaction with Diastereoselectivity The compound shown will undergo an intramolecular Heck reaction to yield a single product with two chiral centers. This process results in diastereoselectivity, meaning that while a new chiral center is formed, only one stereoisomer is obtained. The challenge is to draw the product and provide an explanation for this observed diastereoselectivity. #### Chemical Reaction Details: - **Reactants and Conditions:** - The reactant is a complex organic molecule containing an iodine (I) leaving group and an alkene. - The reaction is facilitated by a palladium acetate catalyst (\[\text{Pd(OAc)}_2\]), triphenylphosphine (\[\text{PPh}_3\]), and triethylamine (\[\text{Et}_3\text{N}\]). - **Visual Description of the Diagram:** - The starting material is a bicyclic compound with a carbon-iodine bond and a nearby alkene double bond. - An intramolecular Heck reaction will occur, promoting the formation of a new carbon-carbon bond while forming a new stereocenter. ### Practice Problem 23.49a: - **Task:** - Draw the product of the reaction. - Include stereochemistry in your answer. This problem encourages students to apply their knowledge of intramolecular Heck reactions by predicting the molecular product with specific attention to stereochemistry. **Interactive Element:** - A "Draw Your Solution" button is provided for students to create and submit their structural prediction.
Transcribed Image Text:### Explanation of Intramolecular Heck Reaction with Diastereoselectivity The compound shown will undergo an intramolecular Heck reaction to yield a single product with two chiral centers. This process results in diastereoselectivity, meaning that while a new chiral center is formed, only one stereoisomer is obtained. The challenge is to draw the product and provide an explanation for this observed diastereoselectivity. #### Chemical Reaction Details: - **Reactants and Conditions:** - The reactant is a complex organic molecule containing an iodine (I) leaving group and an alkene. - The reaction is facilitated by a palladium acetate catalyst (\[\text{Pd(OAc)}_2\]), triphenylphosphine (\[\text{PPh}_3\]), and triethylamine (\[\text{Et}_3\text{N}\]). - **Visual Description of the Diagram:** - The starting material is a bicyclic compound with a carbon-iodine bond and a nearby alkene double bond. - An intramolecular Heck reaction will occur, promoting the formation of a new carbon-carbon bond while forming a new stereocenter. ### Practice Problem 23.49a: - **Task:** - Draw the product of the reaction. - Include stereochemistry in your answer. This problem encourages students to apply their knowledge of intramolecular Heck reactions by predicting the molecular product with specific attention to stereochemistry. **Interactive Element:** - A "Draw Your Solution" button is provided for students to create and submit their structural prediction.
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