Propose an efficient synthesis for the following transformation: A. OMe The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagents 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. HO OH + acid D. H3O+, heat G. Na2Cr₂O7, H₂SO4, H₂O J. SOCI2 B. H HS SH + acid E. [H*], CH3NH2 H. 1) LIAI(OR) 3H; 2) H3O+ K. PCC or DMP C. i + acid F. 1) Et₂ CuLi; 2) H3O+ I. 1) LIAIH4; 2) H3O+ L. RCO 3H

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
Chapter9: Nucleophilic Substitution And Β-elimination
Section: Chapter Questions
Problem 9.54P
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Propose an efficent synthesis.

Propose an efficient synthesis for the following transformation:
A.
OMe
The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary
reagents 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.
HO
OH + acid
D. H3O+, heat
G. Na₂Cr₂O7, H₂SO4, H₂O
J. SOCI₂
B.
H
HS
SH
+ acid
E. [H+], CH3NH2
H. 1) LIAI(OR) 3H; 2) H3O+
K. PCC or DMP
C.
+ acid
F. 1) Et₂CuLi; 2) H3O+
I. 1) LIAIH4; 2) H3O+
L. RCO3H
Transcribed Image Text:Propose an efficient synthesis for the following transformation: A. OMe The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagents 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. HO OH + acid D. H3O+, heat G. Na₂Cr₂O7, H₂SO4, H₂O J. SOCI₂ B. H HS SH + acid E. [H+], CH3NH2 H. 1) LIAI(OR) 3H; 2) H3O+ K. PCC or DMP C. + acid F. 1) Et₂CuLi; 2) H3O+ I. 1) LIAIH4; 2) H3O+ L. RCO3H
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