Consider the following proposed synthesis of (2R,3R)-2,3-dihydroxypentane and (25,3S)-2,3-dihydroxypentane. OH Of the following strategies, which will achieve the given transformation with the correct stereochemistry? Select all that apply. O Reduction to a cis alkene, followed by syn dihydroxylation. Reduction to a trans alkene, followed by syn dihydroxylation. Reduction to a cis alkene, followed by anti dihydroxylation. Reduction to a trans alkene, followed by anti dihydroxylation. Propose an efficient synthesis for the following transformation. s-he The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A t-BUOK E OH conc. H₂SO4, heat B HBr, ROOR F H₂SO4 H₂O, HgSO4 C EtONa G 1) 0₂:2) DMS K D HBr H 1) xs NaNH,; 2) HO

Consider the following proposed synthesis of (2R,3R)-2,3-dihydroxypentane and (25,3S)-2,3-dihydroxypentane. OH Of the following strategies, which will achieve the given transformation with the correct stereochemistry? Select all that apply. O Reduction to a cis alkene, followed by syn dihydroxylation. Reduction to a trans alkene, followed by syn dihydroxylation. Reduction to a cis alkene, followed by anti dihydroxylation. Reduction to a trans alkene, followed by anti dihydroxylation. Propose an efficient synthesis for the following transformation. s-he The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A t-BUOK E OH conc. H₂SO4, heat B HBr, ROOR F H₂SO4 H₂O, HgSO4 C EtONa G 1) 0₂:2) DMS K D HBr H 1) xs NaNH,; 2) HO

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.43P

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