Zoloft

CHEMISTRY 3331: Fundamentals of Organic Chemistry I
Second Exam
Prof. Ognjen S. Vtiljanie
October 23,2009
Name:
(print legibly) Last
Fi rst
Last 4 Diqits of Student ID Number:
./
Read all directions very carefully. Write your answer legibly in the designated spaces and think about
what you are doing. Give only one answer for each question. Total number ofpoints is 270.
1. (28 points) Shown below are structures of a psychedelic illegal drug LSD (left) and antidepressant
Zoloft (right). Each of these two compounds has two chiral centers. In the provided boxes, label each
ofthese stereocenters with an appropriate (R) or (.9) designators.
)
\,/N
o
tE
LSD
o
Zoloft
2. (40 points) Draw the structwes that correspond to the following IUPAC names. Be carefrrl about
stereochemistry-if it is indicated in the name, make sure that your structure reflects it too!
(a) (E) -2-bromo
-3-
fl uoro
-
2
-pentene
(b) l, 1 -divinylcyclobutane
Bn
#
\
I
t_L
I
F
(c)
(I
R,3,S,5R)- 1 -bromo-3-chloro-5-fluorocyclohexane
Br
\^1
tl
\/
I
r
(d) 5 -chloro-7-methyl-
cl
cHr
1,3
-cycloheptadiene
3.
(60 points) Consider the reaction shown below and propose a detailed step-by-step mechanism to
explain the formation of the four products shown. Show each intermediate, all charges, and use
curved arrows to indicate the flow of electrons. Do NOT draw transition states (dotted bonds). A fifth
product with the formula CrHrqO is also formed; draw its structure in the box.
5:
3'r*
5"+L+L+I+
G7H1aO
Ar
\J
^-
$
lHror
o
-1n'
a
..-.lt@
F-'+
)''
4. (56 points) Propose a synthetic route that will achieve the following transformation. NOTE: You will
need to use more than one step in your sequence! Do not show mechanisms.
multiple sfeps
l"/'hu
]'sE"
5.
Of thE FINAL
(4g points) For each of the reactions or series of reactions below, draw the structure
major organic product in the box provided.
t'
?'r
(cH3)3co-K*
T-
>
(cHg)scoH
t-
{
--
el{^
Brz/ hv
N/
K*I- / DMSO
/
O. ftEAcn
or\
\X/
0,^/
6. (38
points) Predict the product of the following reaction:
Br
(GHsleO-K* / (CH3)3COH
H-,
-.,.+g
In the space below, draw the reactive chair conformation that accounts for the formation of
the
product that you predicted for the reaction above. Provide a brief (10 words or less) explanation of
your reasoning.
Bro,n*i,t€ avrol lrTJv"ogen
lu-r* be i,. o#i -foifl&^ur
Co,rStf^cdlo^
"For
EZ.
7. (Bonus credit: 20 points) The reaction shown below is known as the pinacol rcarrangement. Propose
a detailed step-by-step mechanism to explain the formation of the shown product. Show each
intermediate, all charges, and use curved afiows to indicate the flow of electrons. Do NOT draw
tmnsition states (dotted bonds).
H*
-Hzo
-oH
--
)--
-
}*o
rT-
>
,Is2
+fJ
l
)Y