Final Exam

Chemistry 343
Final Exam
December 11, 2001
Name:
ID#:
This exam contains 5 questions on six pages
There are 2 cover pages and three pages at the end.
NOTE: Information on obtaining grades and exams is on the last page

Final C343 Fall 2001
1. /45
2. /45
3. /30
4. /30
5. /50
Total
/200 pts.
1

Final C343 Fall 2001
1. (45 pts) Provide the principle organic product(s) from the reactions below. If no reaction
occurs, provide a brief explanation as to why not.
a)
H 3 C
1.
Cl
O
AlCl 3
2. LDA
3. Br
b)
OH
1. CrO 3
2. SOCl 2
3. H
N
c)
1. O 3 then (CH 3 ) 2 S
2. NaBH 4 (excess)
d)
O
PPh 3
2

Final C343 Fall 2001
e)
1. O 3 then H 2 O 2
2.NaOEt/EtOH
f)
∆
g)
1. hν
2. mCPBA
3

Final C343 Fall 2001
2. (45 pts) Provide reagents (no structures required) capable of accomplishing the indicated
transformations. Some may require more than one step. You may use reagents with as many
carbons in them as you wish. If you can’t remember specific reagents, describe the reaction in
words for partial credit (e.g.’reduction of amide’). Note: question continued on next page; extra
space is to give you room to work, does not mean long answers required
O
O
a)
OH
OH
O
b)
O
OH
O
N
H
c)
Ph
O
Ph
O
Ph
4

Final C343 Fall 2001
O
O
O
d)
e)
CH 3 CH 3
OMe OMe
f)
HN
+
CN
HN
CN
O
O
g)
5

Final C343 Fall 2001
3. (30 pts) Provide reasonable arrow-pushing mechanisms for both steps below. Proton transfers
need not be shown explicitly.
HO
O
NaOEt
EtOH
O
NaOEt
O
O
O
O Ph EtOH
Ph
O
Ph
6

Final C343 Fall 2001
4. (30 pts) Provide reasonable arrow-pushing mechanisms for both steps below. Proton transfers
need not be shown explicitly
O
O
H +
O
NaOCH 3
O
OH
O
H 2 O
O
CH 3 OH
H
H
7

Final C343 Fall 2001
5. (50 pts) Choose TWO OF THE FOUR synthesis problems below. Provide a route to the
indicated target, beginning with the product and working backwards via single step reactions.
If you can not remember the reagents for the forward reaction you will still receive partial
credit as long as the reaction is feasible. Each requires < 5 steps. More space is given on the
next page.
from
HO
O
H 3 C
O
from
H 3 C
product
starting
material
H 3 C
product
OH
H 3 C
starting
material
Choose any 2
H
N
OH
from
from
O
O
H 3 CO OCH 3
product
starting
material
product
starting
material
8

Final C343 Fall 2001
More space for synthesis problems
9

Final C343 Fall 2001
This page intentionally blank: use for scratch paper.
YOU MAY RIP THESE PAGES OFF THE EXAM!
10

Final C343 Fall 2001
This page intentionally blank: use for scratch paper.
YOU MAY RIP THESE PAGES OFF THE EXAM!
11

Final C343 Fall 2001
YOU MAY RIP THIS PAGE OFF THE EXAM
Note: Exam Grades and Course Grades
Will be posted on the course web page
As soon as they are done.
The web page is located at:
http://www.chm.colostate.edu/kennan/c343
Exams themselves may be retrieved from
Julie Van De Velde, Room C326A Chemistry
12