The below synthesis was designed using the Organic Chemistry Roadmaps in the appendix of your textbook. compound a m compound b q Reagents HCI a. b. HBr C. H₂O, H₂SO4 d. Br₂ Cl₂ H₂, Pd Br₂, H₂O Cl₂, H₂O OsO4 then NaHSO3 Hg(OAc)2, H₂O then NaBH4 BH3 then H₂O₂, NaOH O3 then (CH3)2S e f. g. h. i. j. k. I. m. n. 0. p. q. r. 2 equivalents of NaNH₂ H₂, Lindlar's catalyst Na/NH3 H₂SO4, HgSO4 (sia)₂BH then H₂O₂, NaOH 1 equivalent of NaNH₂ compound c In this synthesis, reagents from the table (shown in blue) are used to carry out the indicated reactions. In the box below, draw the structure of compound b. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Consider E/Z stereochemistry of alkenes. • If more than one structure fits the description, draw them all. • If a compound is formed more than once, add another sketcher and draw it again. • If the reaction produces a racemic mixture, draw both stereoisomers. Separate structures with + signs from the drop-down menu.

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The below synthesis was designed using the Organic Chemistry Roadmaps in the appendix of your textbook.
compound a
m
compound b
q
Reagents
a.
HCI
b.
HBr
c. H₂O, H₂SO4
d.
Br2
Cl₂
H₂, Pd
compound c
e.
f.
g.
h.
i.
j.
Br₂, H₂O
Cl₂, H₂O
OsO4 then NaHSO3
k.
I.
m. 2 equivalents of NaNH₂
n.
H₂, Lindlar's catalyst
O.
p.
Hg(OAc)2, H₂O then NaBH4
BH3 then H₂O₂, NaOH
O3 then (CH3)2S
In this synthesis, reagents from the table (shown in blue) are used to carry out the indicated reactions. In the box below, draw the structure of compound b.
q.
r.
Na/NH3
H₂SO4, HgSO4
(sia)₂BH then H₂O₂, NaOH
1 equivalent of NaNH2
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• Consider E/Z stereochemistry of alkenes.
●
If more than one structure fits the description, draw them all.
●
If a compound is formed more than once, add another sketcher and draw it again.
• If the reaction produces a racemic mixture, draw both stereoisomers.
Separate structures with + signs from the drop-down menu.
Transcribed Image Text:The below synthesis was designed using the Organic Chemistry Roadmaps in the appendix of your textbook. compound a m compound b q Reagents a. HCI b. HBr c. H₂O, H₂SO4 d. Br2 Cl₂ H₂, Pd compound c e. f. g. h. i. j. Br₂, H₂O Cl₂, H₂O OsO4 then NaHSO3 k. I. m. 2 equivalents of NaNH₂ n. H₂, Lindlar's catalyst O. p. Hg(OAc)2, H₂O then NaBH4 BH3 then H₂O₂, NaOH O3 then (CH3)2S In this synthesis, reagents from the table (shown in blue) are used to carry out the indicated reactions. In the box below, draw the structure of compound b. q. r. Na/NH3 H₂SO4, HgSO4 (sia)₂BH then H₂O₂, NaOH 1 equivalent of NaNH2 • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Consider E/Z stereochemistry of alkenes. ● If more than one structure fits the description, draw them all. ● If a compound is formed more than once, add another sketcher and draw it again. • If the reaction produces a racemic mixture, draw both stereoisomers. Separate structures with + signs from the drop-down menu.
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