Chemistry 432, Midterm Exam 3 Instructor:
Gustafson
Fall 2015
Name:_______________________________ Be prepared to
show ID upon request.
**No cellular phones or calculators are allowed during the test**
Before you start the exam, make sure that you have 10 problems!! There
are 180 points available, but the exam is only out of 150. You will receive all
points you earn!!! For example if you earn 155/180 points, your grade will go
down as 155/150.
My TA this semester is (please circle):
Lee Wang
Tim Montgomery
Michael Kelly
I do not have a TA this semester.
My student I.D. (red I.D.) number is:
For graders only:
Problem:
#1_________/18p
#2_________/18p
#3_________/18p
#4_________/18p
#5_________/18p
#6_________/ 18p
#7_________/18p
#8_________/ 18p
#9_________/18p
#10________/18p
Total:________/180p
Max total:_______/150p
Good Luck!!!
1) A) Please circle the favored product in each equilibrium. (12 points). B) Please rank
A-E in order of increasing equilibrium constant as written (equilibria favoring the right
are larger (k>1), equilibria favoring the left are smaller(k<1)). The lowest k=1, highest
k=6) Remember pKa tables are provided Big Hint!!! (6 points). Part B is all or
nothing so be careful.
2) Please provide the information asked for below. (Part A is 2 Pts. Part B is 10 Pts,
Part C is 6 Pts, 18 points total).
3) Please provide mechanism for the reactions below. (9 points per part. 18 points
total).
a)
B) Propose a mechanism of the following reaction (enamines are like enols, but more reactive).
4) Predict the products formed in the following reactions (3 per part, 18 Pts total)
5) Please provide the information asked for below. A) 9 points B) 9 points.
A) Please draw the mechanism of 1st cycle of the saponification of a triglyceride. You
only have to draw one ‘deacylation’! You will lose points if your draw more!
B) Propose a mechanism of the following reaction . If a step is repeated multiple times it is OK to
write ‘step repeated’ to save time.
6) A) Please provide a mechanism for the following transformations. (18 points)
1) NaOEt/ EtOH
EtI
2) NaOH (Aq.)
OEt 3) H O/Heat
3
O
H
H
O
Draw product in
Keto Form
7) Predict the products formed in the following reactions (3 per part, 18 Pts total)
8) Please provide the requested information below. 1) 4 points, 2) 8 points, 3) 6 points
(18 total).
O
O
H
O
1
Br
1) Provide Conditions for each product
2) Provide a mechanism for the Thermodynamic product
3)Propose a synthesis of 2 starting from 1 that uses benzyl bromide
2
9) a) In the presence of sodium ethoxide in EtOH the following equilibrium occurs via a
series of Claisen and retro-Claisen condensations. Please provide a mechanism and
explain why the equilibrium favors the right. This is best explained with chemical
structures. We will only consider the first 15 words when grading any written
explanation, SO BE CONCISE. (10 points)
b) Please rank the below compounds in order of increasing acidity (least acidic to most
acidic)(8 points) No partial credit, this is all or nothing.
10) Predict the products formed in the following reactions (3 per part, 18 Pts total)
Scratch Paper
Scratch paper.