Using acetylene and ethylene oxide as your only sources of carbon atoms, propose a synthesis for the following compound: HO OH This target molecule can be prepared from acetylene: HO OH This transformation 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"). There is more than one correct solution, so provide just one answer. A H₂, Pt D TBAF Na, NH3 (1) B 1) NaNH2; 2) ; 3) H3O+ workup E H₂, Lindlar's cat. H NBS, hv C 1) NaNH2; 2) 3) H3O+ workup F ii DMP or PCC I TMSCI, Et3N

Using acetylene and ethylene oxide as your only sources of carbon atoms, propose a synthesis for the following compound: HO OH This target molecule can be prepared from acetylene: HO OH This transformation 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"). There is more than one correct solution, so provide just one answer. A H₂, Pt D TBAF Na, NH3 (1) B 1) NaNH2; 2) ; 3) H3O+ workup E H₂, Lindlar's cat. H NBS, hv C 1) NaNH2; 2) 3) H3O+ workup F ii DMP or PCC I TMSCI, Et3N

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

Section22.SE: Something Extra

Problem 26MP: Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium...

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Question

Propose a strategy for the given synthesis.

Using acetylene and ethylene oxide as your only sources of carbon atoms, propose a synthesis for the following compound:
но
OH
This target molecule can be prepared from acetylene:
HO
OH
This transformation 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"). There is more than one correct solution, so
provide just one answer.
A
H₂, Pt
D
TBAF
G
Na, NH3 (1)
B
1) NaNH2; 2) ° ;
3) H3O+ workup
E
H2, Lindlar's cat.
H
NBS, hv
с
i
3) H3O+ workup
1) NaNH2; 2)
F
DMP or PCC
|
TMSCI, Et3N

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