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):

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Chapter1: Chemical Foundations
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Epoxides can react with alkyne anions to form B-alkynylalcohols.
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 wa
conversion to the same product are possible, show only one of them. Omit steps that are part of the workup procedure.)
Reagents
available
a. NaNH, / NH,
1. TBDMS-CI
b. H₂/Pt
9. Bu,N* F
c. H₂ / Lindlar catalyst h. Na, NH (liq)
d. PCC
i. ethylene axide
e. H₂O
Reagent(s):
Transcribed Image Text:Epoxides can react with alkyne anions to form B-alkynylalcohols. 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 wa conversion to the same product are possible, show only one of them. Omit steps that are part of the workup procedure.) Reagents available a. NaNH, / NH, 1. TBDMS-CI b. H₂/Pt 9. Bu,N* F c. H₂ / Lindlar catalyst h. Na, NH (liq) d. PCC i. ethylene axide e. H₂O Reagent(s):
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