CHEM 3580- Exam II Summer 2013.pdf - Cornell University...

Cornell University
Chemistry 3580
Exam II
July 29, 2013
Instructions: Read all questions completely before answering. You may find it helpful to
first answer those questions that you find easier and then return to those you find more
difficult. Please follow the directions for each question as answers that are not written
where or how it is specified in the question will lose all credit. Good Luck!!!
Problem Score Possible
1 12
2 15
3 15
4 15
5 15
6 15
7 15
8 15
9 15
10 10
11 10
12 10
13 10
14 15
15 13
16 6*
Total 200
*denotes bonus points
Name:___________________________________________________
Signature:________________________________________________

Page 1 of 12
1) ( 12 ) Provide IUPAC names for each of the following compounds or, when a name is
given, draw the corresponding structure. In order to receive any credit, your answer must
be written on the line next to each problem. Be sure to include any stereochemical
designations, where appropriate.
A)
H OH
O O O
B)
Cl
O
C)
O
O
D)
OH
O
S
H
E)
S
F)
O

Page 2 of 12
2) ( 15 ) Propose a reasonable mechanism to account for the formation of the following
observed reaction product(s).
H OH
HO H
H OH
H OH
H OH
H
O
H
H
3
O
+
O
HO
HO
HO
OH
HO

Page 3 of 12
3) ( 15 ) Propose a reasonable mechanism to account for the formation of the following
observed reaction product(s).
N
N N
N
N
H
H
H
2
N
O
H
CH
3
O
H
H
H
3
O
+
N
N N
N
H
H
2
N
O
N
CH
3
H
H

Page 4 of 12
4) ( 15 ) Propose a reasonable mechanism to account for the formation of the following
observed reaction product(s).
OH
1)
Cl S
O
O
N
2)
LiAlH
4
3) H
3
O
+

Page 5 of 12
5) ( 15 ) Propose a reasonable mechanism to account for the formation of the following
observed reaction product(s).
6) ( 15 ) Propose a reasonable mechanism to account for the formation of the following
observed reaction product(s).
OH
H
3
O
+
O
OH
OH
H
3
O
+ O

Page 6 of 12
7) ( 15 ) Propose a reasonable mechanism to account for the formation of the following
observed reaction product(s).
H
3
C
OH
H
3
O
+
HO
H
3
C

Page 7 of 12
8) ( 15 ) Propose a reasonable mechanism to account for the formation of the following
observed reaction product(s).