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Spirocyclic compounds, such as compound 3, are made and used by insects for the purposes of communication. The first step of a synthesis of compound 3 involves treatment of (S)-1,2-epoxypropane (compound 1) with lithium acetylide, followed by acid workup, to give compound 2, as shown below (J. Org. Chem. 2005, 70, 3054-3065). Identify the structure of compound 2 and provide a mechanism for its formation. (Hint: The carbon-lithium bond reacts in a way that is similar to the carbon-magnesium bond of a Grignard reagent.) 1 1) Li—= 2) H3O+ C5H8O 2 3

Spirocyclic compounds, such as compound 3, are made and used by insects for the purposes of communication. The first step of a synthesis of compound 3 involves treatment of (S)-1,2-epoxypropane (compound 1) with lithium acetylide, followed by acid workup, to give compound 2, as shown below (J. Org. Chem. 2005, 70, 3054-3065). Identify the structure of compound 2 and provide a mechanism for its formation. (Hint: The carbon-lithium bond reacts in a way that is similar to the carbon-magnesium bond of a Grignard reagent.) 1 1) Li—= 2) H3O+ C5H8O 2 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
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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Spirocyclic compounds, such as compound 3, are made and used by insects for the purposes of communication. The first step of a synthesis of compound 3 involves treatment of (S)-1,2-epoxypropane (compound 1) with lithium acetylide, followed by acid workup, to give compound 2, as shown below (J. Org. Chem. 2005, 70, 3054-3065). Identify the structure of compound 2 and provide a mechanism for its formation. (Hint: The carbon-lithium bond reacts in a way that is similar to the carbon-magnesium bond of a Grignard reagent.) 1 13.17 a 1) Li—= 2) H₂O+ нас!!!!!! C5H8O Edit Drawing 2 Ž Modify the given structure of the starting material to draw the major product. an 3
Transcribed Image Text:Spirocyclic compounds, such as compound 3, are made and used by insects for the purposes of communication. The first step of a synthesis of compound 3 involves treatment of (S)-1,2-epoxypropane (compound 1) with lithium acetylide, followed by acid workup, to give compound 2, as shown below (J. Org. Chem. 2005, 70, 3054-3065). Identify the structure of compound 2 and provide a mechanism for its formation. (Hint: The carbon-lithium bond reacts in a way that is similar to the carbon-magnesium bond of a Grignard reagent.) 1 13.17 a 1) Li—= 2) H₂O+ нас!!!!!! C5H8O Edit Drawing 2 Ž Modify the given structure of the starting material to draw the major product. an 3
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