Propose an efficient synthesis for the following transformation: 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 t-BUOK E H₂. Lindlar's cat. 1) LIAIH: 2) H₂O' B HBr. ROOR F 1) 0; 2) DMS J DMP or PCC C Na₂Cr₂O7, H₂SO4 H₂O G TsCl, py K conc. H₂SO4, heat D HBr H dilute H₂SO4 L 1) MeMgBr: 2) H₂O'

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
Chapter19: Enolate Anions And Enamines
Section19.9: Crossed Enolate Reactions Using Lda
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Propose an efficient synthesis for the following transformation:
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
t-BUOK
E
H₂ Lindlar's cat.
1) LIAIH: 2) H₂O'
B
HBr. ROOR
F
1) 0; 2) DMS
J
DMP or PCC
с
Na₂Cr₂O7, H₂SO4 H₂O
G
TsCl, py
K
conc. H₂SO4, heat
D
HBr
H
dilute H₂SO4
L
1) MeMgBr: 2) H₂O'
Transcribed Image Text:Propose an efficient synthesis for the following transformation: 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 t-BUOK E H₂ Lindlar's cat. 1) LIAIH: 2) H₂O' B HBr. ROOR F 1) 0; 2) DMS J DMP or PCC с Na₂Cr₂O7, H₂SO4 H₂O G TsCl, py K conc. H₂SO4, heat D HBr H dilute H₂SO4 L 1) MeMgBr: 2) H₂O'
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