Propose an efficient synthesis for the following transformation: ? SH 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.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section: Chapter Questions
Problem 20.54P
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Propose an efficient synthesis for the following transformation:
C
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
B
1) RCO₂H
2) H₂O¹
D
HBr, ROOR
G
Br₂, hv
KMnO4
NaOH, cold
E
SH
1) BH-THF
2) H₂O₂, H₂O
H
NaOEt
C
RCO H
F
t-BUOK
I
NaSH
Transcribed Image Text:Propose an efficient synthesis for the following transformation: C 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 B 1) RCO₂H 2) H₂O¹ D HBr, ROOR G Br₂, hv KMnO4 NaOH, cold E SH 1) BH-THF 2) H₂O₂, H₂O H NaOEt C RCO H F t-BUOK I NaSH
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