Complete the following synthesis road map by (i) providing the structures of the major organic compounds in boxes (A), (B), (C), (D), and (E). (ii) Provide the reagents required to complete each transformation in boxes (a), (b), and (c). Start Here ((а) NANH2 (еxcess) (A) Br Et

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12:01 PM Wed Nov 17
* 65%
T
+: 0
Complete the following synthesis road map by (i) providing the structures of the
major organic compounds in boxes (A), (B), (C), (D), and (E). (ii) Provide the reagents required
to complete each transformation in boxes (a), (b), and (c).
Start Here
((a)
NaNH2
(excess)
((A)
Br
Et
Br
TARGET 2
(C)
Br2, CH;OH
OMe
(c)
Na
|(B)
H.
+
+ enantiomer
+ enantiomer
(b)
(D)
1) NaNH2
2) EtBr
Draw 1 Isomer
Here
Draw 2
Stereoisomers
Here
TARGET 1
OMe
+ enantiomer
OMe
TARGET 3
Na (metal), NH3
SMe
SMe
1) Оз, -78°C
2) DMS
Hints for completing road
maps: Follow each
OMe
(E)
pathway closely (there are
H,
3 different pathways in this
+
question). When/if you get
stuck on a transformation,
look forward down a
+ enantiomer
+ enantiomer
pathway for information
about the next structure
10
Transcribed Image Text:12:01 PM Wed Nov 17 * 65% T +: 0 Complete the following synthesis road map by (i) providing the structures of the major organic compounds in boxes (A), (B), (C), (D), and (E). (ii) Provide the reagents required to complete each transformation in boxes (a), (b), and (c). Start Here ((a) NaNH2 (excess) ((A) Br Et Br TARGET 2 (C) Br2, CH;OH OMe (c) Na |(B) H. + + enantiomer + enantiomer (b) (D) 1) NaNH2 2) EtBr Draw 1 Isomer Here Draw 2 Stereoisomers Here TARGET 1 OMe + enantiomer OMe TARGET 3 Na (metal), NH3 SMe SMe 1) Оз, -78°C 2) DMS Hints for completing road maps: Follow each OMe (E) pathway closely (there are H, 3 different pathways in this + question). When/if you get stuck on a transformation, look forward down a + enantiomer + enantiomer pathway for information about the next structure 10
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