Epoxides can react with alkyne anions to form ?-alkynylalcohols. Starting with 3

Question

Epoxides can react with alkyne anions to form ?-alkynylalcohols.

Starting with 3,5-hexadiyn-1-ol, select reagents from the table below that should be used to synthesize 3,5-octadiyne-1,8-diol.

(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 ways of conversion to the same product are possible, show only one of them.)

Reagents available:

a) NaNH2/NH3

b) H2/Pt

c) H2/Lindlar catalyst

d) PCC

e) H2O

f) TBDMS-Cl

g) Bu4N+F-

h) Na, NH3 (liq)

i) ethylene oxide

Explanation / Answer

faieg

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