Fill in the missing starting material, reagent or product. You may assume that all reagents are provided in excess. Show the appropriate stereochemistry where necessary. If you get stuck, you may buy structure 1, 3, 6, 8, or 9 2 1= 4= 7= HBr ROOR 4 1 Br 2= 5= 8= 10= 5 3 1. 03 2. (CH3)2S 6 1. NaNH, 2. CH₂CH₂Br (3R,4R)-3,4-dichlorohexane (3S,4S)-3,4-dichlorohexane Cl₂ CCI4 3= 6= 9= 8 9 7 1. OsO4 2. H₂O₂

Fill in the missing starting material, reagent or product. You may assume that all reagents are provided in excess. Show the appropriate stereochemistry where necessary. If you get stuck, you may buy structure 1, 3, 6, 8, or 9 2 1= 4= 7= HBr ROOR 4 1 Br 2= 5= 8= 10= 5 3 1. 03 2. (CH3)2S 6 1. NaNH, 2. CH₂CH₂Br (3R,4R)-3,4-dichlorohexane (3S,4S)-3,4-dichlorohexane Cl₂ CCI4 3= 6= 9= 8 9 7 1. OsO4 2. H₂O₂

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

Section9.7: Experimental Evidence For E1 And E2 Mechanisms

Problem 9.7P

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