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 D t-BUOK HBr, ROOR Na2Cr207, H2SO4, H2O HBr H2, Lindlar's cat. O MeMgBr; 2) H3O* TSCI, py dilute H2SO4 DMP or PCC conc. H2SO4. heat 1) EtMgBr: 2) H30* 1) LIAIH4; 2) H3O* eTextbook and Media Hint !!

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
C
t-BuOK
HBr, ROOR
Na2Cr207, H2SO4, H2O
HBr
H2, Lindlar's cat.
1) MeMgBr; 2) H3O*
TSCI, py
dilute H2SO4
DMP or PCC
conc. H2SO4, heat
1) EtMgBr; 2) H3O*
1) LIAIH4; 2) H:0*
eTextbook and Media
Hint
!!
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 C t-BuOK HBr, ROOR Na2Cr207, H2SO4, H2O HBr H2, Lindlar's cat. 1) MeMgBr; 2) H3O* TSCI, py dilute H2SO4 DMP or PCC conc. H2SO4, heat 1) EtMgBr; 2) H3O* 1) LIAIH4; 2) H:0* eTextbook and Media Hint !!
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