Propose an efficient synthesis for the following transformation: OH The transformation above 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"). If there is more than one correct solution, provide just one answer. t-BUOK HBr, ROOR Na2Cr207, H2SO4, H20 HBr G H H2, Lindlar's cat. 1) MеMgBr; 2) H,0+ TSCI, py dilute H2SO4 I K 1) LIAIH,; 2) H,0+ DMP or PCC conc. H2SO4, heat 1) EtMgBr; 2) H,0+

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter9: Alkynes: An Introduction To Organic Synthesis
Section9.SE: Something Extra
Problem 40AP
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Propose an efficient synthesis for the following transformation:
OH
The transformation above 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"). If there is more than one correct solution, provide just one answer.
A
В
C
t-BUOK
HBr, ROOR
Na2Cr207, H2S04, H20
HBr
E
F
G
H
H2, Lindlar's cat.
1) МеMgBr; 2) H,о+
TSCI, py
dilute H2SO4
I
J
K
L
1) LIAIH,; 2) H,0+
1) EtMgBr; 2) H,0+
DMP or PCC
conc. H2SO4, heat
Transcribed Image Text:Propose an efficient synthesis for the following transformation: OH The transformation above 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"). If there is more than one correct solution, provide just one answer. A В C t-BUOK HBr, ROOR Na2Cr207, H2S04, H20 HBr E F G H H2, Lindlar's cat. 1) МеMgBr; 2) H,о+ TSCI, py dilute H2SO4 I J K L 1) LIAIH,; 2) H,0+ 1) EtMgBr; 2) H,0+ DMP or PCC conc. H2SO4, heat
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