Final Exam
December 15, 2004
The Final Exam is similar to the Mid-Term Exam, except that the
final covers all 12 experiments. See the file labeled Mid-Term Exam for
more details. An example of a Final Exam is provided, starting on the next
page.
Lab 15
1
Prince George's Community College
CHM 204 Final Exam
200 Points, 10 each question.
Spring 2004
Name_________________
1. Complete the reaction for the reduction of benzophenone. Draw the structure of the organic covalent
product of the reaction and show all reagents necessary to obtain it.
O
C
+
2. Draw the structure obtained on the sodium borohydride reduction of the following compound
after acidification.
O
O
CCH3
3. Circle the oxidizing agents in the group below.
HCl
HNO3
KMnO4
KOH
NaBH4
K2Cr2O7
4. Show the result of the following reaction.
O
K2Cr2O7
CH3CCH3 +
5. Write an equation for the reaction of 2-furfuraldehyde with semicarbazide.
6 a. Does a simple aldehyde have a UV absorption? Yes___ No____
b. If so, indicate the orbital transition that occurs when an aldehyde absorbs UV light? ___________
7. Show the equation for the Diels-Alder reaction between 1,3-butadiene and maleic anhydride.
8. Write an equation for the preparation of ethyl benzoate by a Fischer esterification.
9. Identify the organic families in the following partial structures.
O
O
CNHCH3
CH
O
CH2CCH3
O
COH
10. Show the major product of the following reaction.
(1) CH3MgI
O
Lab 15
(2) H +/H2O
2
11. Write an equation for the hydrolysis of acetic anhydride.
12. Write an equation for the acetylation of salicylic acid, as you performed it in the lab.
Complete the following equations. (The mechanism is not required.)
13.
(CH3)2CHCl
+
14.
AlCl3
Br2
NO2
Fe
15.
N2+
+
16.
?
N2+
NH2
+
17. Write an equation for the reaction between o-methylaniline and acetyl chloride.
18. Write an equation for the reaction between acetyl chloride and water.
19. Draw the structure of -D-glucopyranose in a Haworth projection.
20. A compound C10H16 gives 2,6-dimethyloctane on catalytic hydrogenation
and the following products on ozonolysis with a reductive workup. Give the
IUPAC name of the compound.
C10H16
Lab 15
C3H6O
+ C3H4O2 + C3H4O2 + CH2O
3
Prince George's Community College
CHM 204 Final Exam
200 Points, 10 each question.
Spring 2004
Name_________________
1. Complete the reaction for the reduction of benzophenone. Draw the structure of the organic covalent
product of the reaction and show all reagents necessary to obtain it.
O
OH
(1) NaBH4
C
C
+
(2) H+ or H2O
H
2. Draw the structure obtained on the sodium borohydride reduction of the following compound
after acidification.
OH
O
O
HO
CCH3
CHCH3
3. Circle the oxidizing agents in the group below.
HCl
HNO3
KMnO4
KOH
NaBH4
4. Show the result of the following reaction.
O
K2Cr2O7
CH3CCH3 +
K2Cr2O7
No Reaction
5. Write an equation for the reaction of 2-furfuraldehyde with semicarbazide.
O
O
+
CHO
O
O
H2NNCNH2
CH=NNHCNH2
H
x No____
6 a. Does a simple aldehyde have a UV absorption? Yes___
n

b. If so, indicate the orbital transition that occurs when an aldehyde absorbs UV light? ___________
7. Show the equation for the Diels-Alder reaction between 1,3-butadiene and maleic anhydride.
O
O
+
O
O
O
O
8. Write an equation for the preparation of ethyl benzoate by a Fischer esterification.
CO2H
+
CH3CH2OH
H+, heat
CO2CH2CH3
9. Identify the organic families in the following partial structures.
O
O
amide
CNHCH3
O
aldehyde
ketone
CH2CCH3
CH
O
acid
COH
10. Show the major product of the following reaction.
(1) CH3MgI
O
Lab 15
(2) H +/H2O
OH
4
11. Write an equation for the hydrolysis of acetic anhydride.
Ac2O
H2O
2 AcOH
12. Write an equation for the acetylation of salicylic acid, as you performed it in the lab.
OH
+
OAc
Ac2O
CO2H
CO2H
Complete the following equations. (The mechanism is not required.)
CH(CH3)2
13.
(CH3)2CHCl
+
14.
Friedel-Crafts
NO2
Br2
NO2
Fe
halogenation
15.
N2+
+
16.
AlCl3
Br
H3PO2
?
N2+
NH2
N N
+
NH2
17. Write an equation for the reaction between o-methylaniline and acetyl chloride.
NH2
AcCl
NHAc
18. Write an equation for the reaction between acetyl chloride and water.
H2O
AcCl
AcOH
19. Draw the structure of -D-glucopyranose in a Haworth projection.
CH2OH
O
H
OH
OH
H
H
OH
H
OH
20. A compound C10H16 gives 2,6-dimethyloctane on catalytic hydrogenation
and the following products on ozonolysis with a reductive workup. Give the
IUPAC name of the compound.
C10H16
C3H6O
+ C3H4O2 + C3H4O2 + CH2O
3,7-dimethylocta-1,3,6-triene
Lab 15
5