(a) (b) (c) ОН -OH OH ? -CH₂OH ? (d) О CHOH CH₂OH ? ? moilosot not in ее 2010 о о (e) H (f) -CH₂CI ? -O-*K ? ? -ОН KMnO4 Н (h) н ОН uslucolomsnni gniwollot od to raubong adll biber (2) ? OCH₂CH3 OCH3 -OCH3 Н OTS -Н

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 64AP: The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold...
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Provide a reagent that will complete the transformations.
(a)
(c)
(d)
OH
OH
OH
-CH2OH
? msidong done towane mobivo
ii
?
?
?
a -CH₂OH
moiloser nobibl
en gniwolloi
H (f)
-CH₂CI
-O+K
IBD
?
KMnO4
?
OCH₂CH3
Oº
OCH 3
-OCH3
H
I ~:
(h)
OH
H
OH
usluostomsnni gniwollot od to rubong add toibert (2).85
H
OTS
-H
Transcribed Image Text:(a) (c) (d) OH OH OH -CH2OH ? msidong done towane mobivo ii ? ? ? a -CH₂OH moiloser nobibl en gniwolloi H (f) -CH₂CI -O+K IBD ? KMnO4 ? OCH₂CH3 Oº OCH 3 -OCH3 H I ~: (h) OH H OH usluostomsnni gniwollot od to rubong add toibert (2).85 H OTS -H
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