Starting with 3,5-hexadiyn-1-ol, select reagents from the table below that should be used to synthesize 1,8-octanediol. 3,5-hexadiyn-1-ol 1,8-octanediol (The reaction may require more than one step; if so, write the letters in the order that they are used, e.g., abc. If two or more in conversion to the same product are possible, show only one of them. Omit steps that are part of the workup procedure.) Reagents available a. NINH, / NH, 1. TBDMS-CI b. H₂/Pt 9. Bu,N*F c. H₂/ Lindlar catalyst h. Na, NH (lig) d. PCC Lethylene oxide e. H₂O Reagent(s):

Starting with 3,5-hexadiyn-1-ol, select reagents from the table below that should be used to synthesize 1,8-octanediol. 3,5-hexadiyn-1-ol 1,8-octanediol (The reaction may require more than one step; if so, write the letters in the order that they are used, e.g., abc. If two or more in conversion to the same product are possible, show only one of them. Omit steps that are part of the workup procedure.) Reagents available a. NINH, / NH, 1. TBDMS-CI b. H₂/Pt 9. Bu,N*F c. H₂/ Lindlar catalyst h. Na, NH (lig) d. PCC Lethylene oxide e. H₂O Reagent(s):

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

Chapter6: Reactions Of Alkenes

Section: Chapter Questions

Problem 6.38P: Reaction of -pinene with borane followed by treatment of the resulting trialkylborane with alkaline...

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