Propose an efficient synthesis for the following transformation: (b) Br 1 The transformation above can be performed with come ro mbination gonts listed b

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Propose an efficient synthesis for the following transformation:
(b)
1)
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.
A
H
2) H30+
E
TsCl, pyridine
1
Br
PCC or DMP
-
B
CI
NaOEt
F
Ph3P=CH2
+ AICI 3
J
1)
2) H3O+
t-BuOK
C
G
K
Na2Cr2O7, H2SO4, H₂O
Mg
D
H
conc. H₂SO4, heat
L
OSO4, cat. NMO
Transcribed Image Text:Propose an efficient synthesis for the following transformation: (b) 1) 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. A H 2) H30+ E TsCl, pyridine 1 Br PCC or DMP - B CI NaOEt F Ph3P=CH2 + AICI 3 J 1) 2) H3O+ t-BuOK C G K Na2Cr2O7, H2SO4, H₂O Mg D H conc. H₂SO4, heat L OSO4, cat. NMO
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