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Natural products that contain the N-1,1-dimethyl-2-propenyl group often exhibit antifungal or antitumor activity. The synthesis of one such compound begins with the two steps shown here. OAc C13H15N CuCI, -Pr,NEt 2 a. Draw the structure of compound 2 and show a reasonable mechanism for its formation. CuCl is used as a catalyst (behaving similarly to an acid) and i-PR2NET is a base. The former can be ignored in your mechanism. b. Identify the reagents necessary for the conversion of 2 to 3.

Natural products that contain the N-1,1-dimethyl-2-propenyl group often exhibit antifungal or antitumor activity. The synthesis of one such compound begins with the two steps shown here. OAc C13H15N CuCI, -Pr,NEt 2 a. Draw the structure of compound 2 and show a reasonable mechanism for its formation. CuCl is used as a catalyst (behaving similarly to an acid) and i-PR2NET is a base. The former can be ignored in your mechanism. b. Identify the reagents necessary for the conversion of 2 to 3.

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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### Activity: Organic Synthesis Pathway Natural products that contain the N-1,1-dimethyl-2-propenyl group often exhibit antifungal or antitumor activity. The synthesis of one such compound begins with the two steps shown here. **Reaction Scheme:** 1. Starting Material: Compound 1 (Indole structure) 2. Intermediate: Compound 2 (product of the reaction with acetoxydimethylpropyne and base) 3. Final Product: Compound 3 (possessing the N-1,1-dimethyl-2-propenyl group) **Reaction Steps:** - **Step 1:** - Reagents: Acetoxydimethylpropyne (shown with OAc leaving group), CuCl (catalyst), and i-Pr2NEt (base). - Transformation: Compound 1 reacts to form compound 2 via an intermediate step. - **Step 2:** - Compound 2 is further processed to yield Compound 3. **Structural Diagrams:** - **Compound 1:** The structure is an indole with a secondary amine at the nitrogen position. - **Compound 2:** This structure is derived from the reaction but needs to be drawn specifically. - **Compound 3:** The final structure is an indole with an N-1,1-dimethyl-2-propenyl group attached to the nitrogen. **Questions:** **a. Draw the structure of compound 2 and show a reasonable mechanism for its formation. CuCl is used as a catalyst (behaving similarly to an acid) and i-Pr2NEt is a base. The former can be ignored in your mechanism.** - For this task, students would need to: - Identify the structure of Compound 2 based on its precursor (indole) and the chemical reagents provided. - Show the steps in the mechanism, illustrating how the base i-Pr2NEt facilitates the reaction to form Compound 2. **b. Identify the reagents necessary for the conversion of 2 to 3.** - Here, students must determine which chemical reagents would be used to convert the intermediate Compound 2 to the final product Compound 3, highlighting the functional group transformation that takes place. **Graph/Diagram Descriptions:** - The reaction schematic shows linear progression from Compound 1 (starting material) to Compound 3 (final product), with an
Transcribed Image Text:### Activity: Organic Synthesis Pathway Natural products that contain the N-1,1-dimethyl-2-propenyl group often exhibit antifungal or antitumor activity. The synthesis of one such compound begins with the two steps shown here. **Reaction Scheme:** 1. Starting Material: Compound 1 (Indole structure) 2. Intermediate: Compound 2 (product of the reaction with acetoxydimethylpropyne and base) 3. Final Product: Compound 3 (possessing the N-1,1-dimethyl-2-propenyl group) **Reaction Steps:** - **Step 1:** - Reagents: Acetoxydimethylpropyne (shown with OAc leaving group), CuCl (catalyst), and i-Pr2NEt (base). - Transformation: Compound 1 reacts to form compound 2 via an intermediate step. - **Step 2:** - Compound 2 is further processed to yield Compound 3. **Structural Diagrams:** - **Compound 1:** The structure is an indole with a secondary amine at the nitrogen position. - **Compound 2:** This structure is derived from the reaction but needs to be drawn specifically. - **Compound 3:** The final structure is an indole with an N-1,1-dimethyl-2-propenyl group attached to the nitrogen. **Questions:** **a. Draw the structure of compound 2 and show a reasonable mechanism for its formation. CuCl is used as a catalyst (behaving similarly to an acid) and i-Pr2NEt is a base. The former can be ignored in your mechanism.** - For this task, students would need to: - Identify the structure of Compound 2 based on its precursor (indole) and the chemical reagents provided. - Show the steps in the mechanism, illustrating how the base i-Pr2NEt facilitates the reaction to form Compound 2. **b. Identify the reagents necessary for the conversion of 2 to 3.** - Here, students must determine which chemical reagents would be used to convert the intermediate Compound 2 to the final product Compound 3, highlighting the functional group transformation that takes place. **Graph/Diagram Descriptions:** - The reaction schematic shows linear progression from Compound 1 (starting material) to Compound 3 (final product), with an
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