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Post Lab Questions: Bromination of E-Stilbene
1. (2 pts) Calculate the theoretical mass of the desired stilbene dibromide product that you would expect to obtain for the bromination of (E)-stilbene.
2. Calculate percent yield (% yield) of the stilbene dibromide product from the bromination of (E)-stilbene.
3. Is there any other possible product could be formed from the bromination of (E)-stilbene or trans-stilbene?
4. Identify stereoisomeric relationship of the product from the bromination of (E)-stilbene or trans-stilbene. (Meso compound / Racemic mixture / R enantiomer only / S enantiomer only?)
5. (2pts) An organic chemist has found that the bromination of (Z)-stilbene or cis-stilbene leading to two possible isomers of the products. Provide the two products formed from the bromination of (Z)-stilbene or cis-stilbene including their proper stereochemistry.
6. Identify stereoisomeric relationship between the products answer in question 5. (Meso compound / Racemic mixture / R enantiomer only / S enantiomer only?)
7. (2 pts) Another important concept of Green Chemistry is atomic economy and less toxic waste disposal. Compare the following three bromination reactions and identify which of the following reactions is the most atomic economic and least toxic. Justify which reaction would be the best bromination to perform.
6
HH
(Z)-Stilbene or cis-Stilbene
+ Br
2
+
H
H
H
H
Br
Br
Br
2
CH
2
Cl
2
r
e
a
c
t
i
o
n
1
reaction 2
EtOH
HBr/H
2
O
2
r
e
a
c
t
i
o
n
3
NHBr
3
H
H
Br
Br
H
H
Br
Br
EtOH
+ H
2
O
+
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