CHEM 232 San Diego State Reactivity of Enolates Towards Esters Questions

Each team or individual can chose any of the below FDA approved drugs. You must use reactions that we have learnedin chem 232 or chem 432. Please note that I am aware that the synthesis of these drugs are readily available online,
and it is very easy for me to tell when a student is just plagiarizing the synthesis from wikipedia or a related source. I
am prepared to give students that do this 0/66. Please honor the spirit of this assignment and have you or your team
turn in your work! Do not worry about chirality, or making aromatic rings from scratch. in ‘real life’ we normally ‘buy
the rings’ and incorporate them into the molecule.
Please provide a synthesis of the molecule assigned to your team. Each of these molecules are
FDA approved drugs that have made it to patients in the last 5 years. You don’t need to, but I
encourage you to look into what your team’s molecule is used for. Some drugs come as a salt.
Do not worry about the counterion, just make the drug.
No need to worry about chirality or forming any rings from scratch.
HN
HN
TAZVERIK
Question 2
28 pts
Please choose the correct product for the below transformations. Please indicate whether each
reaction goes through a kinetic enolate, thermodynamic enolate, enol or enamine mechanism.
A
B
с
1
1
les the longe
y lot
Line
13 Como
Then H2O
A
B
с
A
3)
1
1
1
1) H+
NH
NH
NH
B
с
A
C
Br
Br
10% a
NH
4)
А
B
с
MeO-Na in MeOH
5)
HO
A
B
с
1 is
and goes via a
mechanism
2 is
and goes via a
mechanism
3 is
and goes via a
mechanism
4 is
and goes via a
mechanism
5
5 is
and goes via a
mechanism
Question 3
35 pts
each part is worth 17.5 points.
A) Please provide a mechansim for question 2 part 1, and explain why we get
the product
B) Provide a mechansim for teh Robinson annulation in question 2. please
identify the ‘substeps’ by their name (i.e. Michael addition, aldol dehydration..)
D
Question 6
34 pts
A) please provide the mechansim for the below transformation (17 points)
NaOH, Bra
-NH2
NH2
B) please provide a mechanism for teh following transformation (17 points)
NH, H-o
N=0
H2SO4
NON
then
ОН
OH
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Question 9
25 pts
PPh
1)
Php
Php
Rh.
H
Me
&
H2 (gas)
Me
Me
B
H
Me
с
А.
2) CI
Br
Ph
HOB-OH
Br
다.
Pd(PPhg)
K_CO,
A
B
с
3)
Pd(PPhg)
K CO,
A
B
с
Reaction 1 is
Reaction 2 is
Reaction 3 is
Question 10
20 pts
Please provide the general mechanism for the hydrogenation from the previous question
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12ptParagraph | BI V Ave Tv
р
O words

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