What is the mechanism for this series of reactions?

Principles of Modern Chemistry
8th Edition
ISBN:9781305079113
Author:David W. Oxtoby, H. Pat Gillis, Laurie J. Butler
Publisher:David W. Oxtoby, H. Pat Gillis, Laurie J. Butler
Chapter14: Chemical Equilibrium
Section: Chapter Questions
Problem 94AP
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What is the mechanism for this series of reactions? 

compound e
compound d
m
compound c
compound b
b
compound a
Reagents
1 equiv. NaNH2
h. H2, Lindlar's catalyst
i.
a.
Br2, hv
g.
m.
H2CrO4
b.
K* tBuO
SOCII2
n.
C.
NBS
HBr, H2O2
o.
Hg(OAc)2 then NaBH4
d.
H2, Pd/C
j.
Mg, ether
р.
Br2, CH3CO2H
CO2 then H30*
O3 then (CH3)2S
е.
NaOH
k.
f.
Cat. H2SO4
I.
This synthesis was designed using the roadmaps from the appendix of your textbook.
Follow through the series of reactions, and draw the structures of compound a and compound e in the appropriate sketchers below.
Transcribed Image Text:compound e compound d m compound c compound b b compound a Reagents 1 equiv. NaNH2 h. H2, Lindlar's catalyst i. a. Br2, hv g. m. H2CrO4 b. K* tBuO SOCII2 n. C. NBS HBr, H2O2 o. Hg(OAc)2 then NaBH4 d. H2, Pd/C j. Mg, ether р. Br2, CH3CO2H CO2 then H30* O3 then (CH3)2S е. NaOH k. f. Cat. H2SO4 I. This synthesis was designed using the roadmaps from the appendix of your textbook. Follow through the series of reactions, and draw the structures of compound a and compound e in the appropriate sketchers below.
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