Question 15 Propose an efficient synthesis for the following transformation: "he transformation above can be performed with some reagent or combination of the reagents listed below. Give the ecessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there s more than one correct solution, provide just one answer. A в D t-BUOK HBr, ROOR Na,Cr207, H2SO4, H20 HBr E F G H H2, Lindlar's cat. TSCI, py dilute H,SO4 1) MeMgBr; 2) H3O* к 1) LIAIH4: 2) H3O* DMP or PCC conc. H2SO4, heat 1) BH3-THF; 2) H2O2, NaOH

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Please provide a complete reaction mechanism (This includes arrow pushing mechanism, resonance stabilization, charges for instance). You can choose what question to answer. Correct answers for the final product and its reactants are provided. I hope I can receive a complete answer as much as possible. 

Question 15
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
в
t-BUOK
HBr, ROOR
Na,Cr207, H2SO4.
H20
HBr
E
F
G
1) MeMgBr; 2)
H30*
H2, Lindlar's cat.
TSCI, py
dilute H2SO4
K
1) LIAIH4; 2)
H3O*
conc. H2SO4, heat
1) BH3-THF; 2) H2O2,
DMP or PCC
NaOH
IGA
1) LAH
2) H20
3) TSCI, py
4) t-BUOK
1) LAH
2) H20
он
OTs
t-BUOK
TSCI,
pyridine
Transcribed Image Text:Question 15 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 в t-BUOK HBr, ROOR Na,Cr207, H2SO4. H20 HBr E F G 1) MeMgBr; 2) H30* H2, Lindlar's cat. TSCI, py dilute H2SO4 K 1) LIAIH4; 2) H3O* conc. H2SO4, heat 1) BH3-THF; 2) H2O2, DMP or PCC NaOH IGA 1) LAH 2) H20 3) TSCI, py 4) t-BUOK 1) LAH 2) H20 он OTs t-BUOK TSCI, pyridine
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