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Problem 3 Purpose: Understanding the limitations of the reactions we know is critical for correct application of those reactions. Just because we want a particular reaction to work does not mean it will! In this problem, you will assess two proposed syntheses and identify the error in them. Presentation instructions: A group will collectively present this question. Problem: Each of the syntheses below proposes a sequence of reactions that, unfortunately, will not successfully create the desired final product. Identify the step(s) in each synthesis that is/are problematic and justify your selections. a) b) OH 1) SOCI₂, pyr 2) H3O+ OTS HO 3) TsCl, pyr Cl 1) Na2Cr2O7, H2SO4, H2O 2) EtMgBr (xs) 3) H3O+ OH HO OH

Problem 3 Purpose: Understanding the limitations of the reactions we know is critical for correct application of those reactions. Just because we want a particular reaction to work does not mean it will! In this problem, you will assess two proposed syntheses and identify the error in them. Presentation instructions: A group will collectively present this question. Problem: Each of the syntheses below proposes a sequence of reactions that, unfortunately, will not successfully create the desired final product. Identify the step(s) in each synthesis that is/are problematic and justify your selections. a) b) OH 1) SOCI₂, pyr 2) H3O+ OTS HO 3) TsCl, pyr Cl 1) Na2Cr2O7, H2SO4, H2O 2) EtMgBr (xs) 3) H3O+ OH HO OH

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter15: Radical Reactions
Section: Chapter Questions
Problem 12E
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Problem 3 Purpose: Understanding the limitations of the reactions we know is critical for correct application of those reactions. Just because we want a particular reaction to work does not mean it will! In this problem, you will assess two proposed syntheses and identify the error in them. Presentation instructions: A group will collectively present this question. Problem: Each of the syntheses below proposes a sequence of reactions that, unfortunately, will not successfully create the desired final product. Identify the step(s) in each synthesis that is/are problematic and justify your selections. a) b) OH 1) SOCI₂, pyr 2) H3O+ OTS HO 3) TsCl, pyr Cl 1) Na2Cr2O7, H2SO4, H2O 2) EtMgBr (xs) 3) H3O+ OH HO OH
Transcribed Image Text:Problem 3 Purpose: Understanding the limitations of the reactions we know is critical for correct application of those reactions. Just because we want a particular reaction to work does not mean it will! In this problem, you will assess two proposed syntheses and identify the error in them. Presentation instructions: A group will collectively present this question. Problem: Each of the syntheses below proposes a sequence of reactions that, unfortunately, will not successfully create the desired final product. Identify the step(s) in each synthesis that is/are problematic and justify your selections. a) b) OH 1) SOCI₂, pyr 2) H3O+ OTS HO 3) TsCl, pyr Cl 1) Na2Cr2O7, H2SO4, H2O 2) EtMgBr (xs) 3) H3O+ OH HO OH
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