Organic Chemistry 302
Examination Three-April 13, 1999
I. (Five points each) Synthesize the following:
II.
(Four points each) Write a complete mechanism for each of the
reactions in the following sequence.
III.
(Three points each) Complete the following reactions:
|
a. cyclohexanone |
+ |
KMnO4 |
® |
|
b. acetaldehyde |
+ |
LAH |
® |
|
|
c. 2
acetone + OH |
® |
|
d. cyclopentanone |
+ NaBH4 |
® |
|
e. butanone + |
2,4-DNP ® |
|
f. cyclopentanone + excess
methanol/OH |
® |
|
g. benzaldehyde + cyclohexanone/OH |
® |
|
h. 2-propanol |
+ K2Cr2O7 ® |
IV.
(Four points each)
a.
Why
are acetals stable in base, but not in acid?
b.
What
kind of error can a bad thermometer introduce in the distillation experiment?
V.
(Fifteen points) Consider compound A:
Compound A (C6H12O)
|
A |
+ |
KMnO4 |
® |
n.r. |
|
A |
+ |
Br2/CCl4 |
® |
n.r. |
|
A |
+ |
Ag(NH3)2+ |
® |
n.r. |
A |
+ |
NaBH4 |
|
® |
B |
B + H+ ® |
C + D + EMajor Minor |
C |
+ |
H2O/H+ |
® |
F |
D |
+ |
H2O/H+ |
® |
F |
C |
+ |
B2H6/H2O2 |
® |
B |
D |
+ |
B2H6/H2O2 |
® |
B |
F |
+ |
KMnO4 |
® |
n.r. |
|
E |
+ |
H2O/H+ |
® |
B |
|
E |
+ |
B2H6/H2O2 |
® |
G |
|
G |
+ |
CrO3/pyridine |
® |
H |
|
H |
+ |
KMnO4 |
® |
brown
ppt. |
|
H |
+ |
Ag(NH3)2+ |
® |
silver
mirror |
|
C |
+ |
O3/Zn,H+ |
® |
I |
+ |
J |
|
C |
+ |
O3/H2O2 |
® |
K |
+ |
J |
|
D |
+ |
O3/Zn,H+ |
® |
I |
+ |
J |
|
D |
+ |
O3/H2O2 |
® |
K |
+ |
J |
|
E |
+ |
O3/Zn,H+ |
® |
L |
+ |
M |
|
E |
+ |
O3/H2O2 |
® |
N |
+ |
M |
Identify
A through M.