Chem 242
Final Exam Practice
Summer 2010
1. Draw the product of each reaction below, and give the reaction mechanism (SN1, SN2, E1, E2).
Mechanism
CH3OH
+
I
Br
+
OTs
CH3S -
+
acetone
:C N
CH3CN
Br
+
EtO - Na+
EtOH
2. Reactions of alkenes with halogens: give the expected product in each case. Be sure to think about
reaction mechanisms (and resonance structures for the second reaction).
CH3
+
Br2
CH3
CCl4
uv
+
NBS
CCl4
3. How many separate signals should the following compounds show in the 1H NMR spectrum?
PCl2
CH3-O-CH2CH2CH3
O
O
Br
4. Circle the strongest nucleophile in each pair below.
H2O and
Me2NH and
HOMeOH
R-SH
Et3P:
and
and
R-OH
Et4P+
5. A compound of molecular formula C5H10O is shown by chemical tests to contain a carbonyl group
(C=O). The 1H NMR shows the following signals:
doublet
1.3 ppm
6 H’s
Propose a structure for this compound.
singlet
2.1 ppm
2 H’s
multiplet
2.6 ppm
1H
6. Give products for the following reactions (after aqueous workup if needed).
O
+
CH3MgBr
Et2O
O
Li
+
C6H12
HO
O
2 Et-MgCl
+
R
THF
OMe
O
Cl
+
CH3-MgBr
Et2O
7. In the following molecules, circle any parts of the structure that contain conjugated double bonds.
OMe
O
OMe
+
NO2
8. Outline a two-step procedure for the synthesis of the compound shown,
starting with benzene. Give all reagents for each reaction.
Cl
9. Show how the following compounds could be synthesized from methane.
a. propane
b. methyl isopropyl ether
c. 1-butene
d. methyl acetate
10. Give the major product(s) for the following reactions of substituted aromatic systems.
Cl2
+
CF3
FeCl3
O
+
CH3C -Cl
+
HNO3
AlCl3
cat. H+
HO
O
+ SO3/H2SO4
11. Show how each starting materials could be transformed into the product shown. Give reagents and
draw the product for each step.
OH
OH
O
OH
OH
OH
CH3
12. Give products for the following reactions of the alcohol shown.
OH
HBr
+
CH2Cl2
OH
+
H2SO4
H2O
OH
CrO3
+
H2O/acetone
13. Draw examples of the following:
a. a monosaccharide that is an aldose and a pentose (five carbons) in the open chain form
b. a ketose that is a hexose in the cyclic hemiacetal form
c. any disaccharide
14. a. Circle the compounds below that could be carbohydrates. Classify each one (monosaccharide vs.
disaccharide, pentose vs. hexose, aldose vs. ketose).
CHO
H
HO
H
OH
HO
O
H
OH
CH2OH
O
O
OH
HO
HO
CH2OH
OH
HO
OH
HO
HO
O
HO
OH
OH
OMe
OH