8. (18 points) Draw the structures of the intermediates (A, B, and C) and of the final product (D) in the
multistep synthesis reactions given below, showing stereochemistry if needed. If you are unable to
draw the structures, you can get partial credit by describing what type of reaction the reagents are used
for.
a.
b.
C.
Br
Br₂, hv
DBU
► A
NaNH,
A
Br₂
NaOEt B
heat
B
1. NaNH, (2 eq.)
2. H₂O
CH3-Br
HBr
ROOR
B
C
Na, NH3
C
NaSCH3
1. (Sia)₂BH
2. H₂O₂, NaOH
C
→ D
1. MCPBA
2. H₂O+
D
D