Propose an efficient synthesis for the given transformation. This transformation 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 E 1) ; 2) Mg H2, Lindlar's NaH cat. H30* 2) H30* F G H J HBr (xs), heat 1) MeMgBr; 2) H3O* Na, NH3 МСРВА 1) EtMgBr; (1) (RCO3H) 2) H30* K L M N dilute H2SO4 SOCI2, pyridine DMP or EtBr 1) BH3-THF; РСС 2) H2O2, NaOH

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
Chapter8: Haloalkanes, Halogenation, And Radical Reactions
Section: Chapter Questions
Problem 8.28P
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Propose an efficient synthesis for the given transformation.
This transformation 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
D
E
1)
; 2)
1) ° ;
Mg
H2, Lindlar's
NaH
cat.
H30*
2) H30*
F
G
H
1) MeMgBr;
1) EtMgBr;
2) H30*
HBr (xs), heat
Na, NH3
(1)
МСРВА
2) H30*
(RCO3H)
K
L
M
N
SOCI2,
pyridine
dilute H2SO4
1) BH3-THF;
2) H2O2,
DMP or
EtBr
РСС
NaOH
Transcribed Image Text:Propose an efficient synthesis for the given transformation. This transformation 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 D E 1) ; 2) 1) ° ; Mg H2, Lindlar's NaH cat. H30* 2) H30* F G H 1) MeMgBr; 1) EtMgBr; 2) H30* HBr (xs), heat Na, NH3 (1) МСРВА 2) H30* (RCO3H) K L M N SOCI2, pyridine dilute H2SO4 1) BH3-THF; 2) H2O2, DMP or EtBr РСС NaOH
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Synthesis of desired product can be reached in different ways. But, I will discuss the most effective one. 

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