Organic Chemistry Practice Exam 2
Chapter 3: Alkenes & Alkynes
1. Label ALL functional groups in the following molecules:
O
F
SH
OH
O
NH2
a. HO
b.
O
2. Name the following molecules. Be sure to indicate stereochemistry IF APPLICABLE.
Br
Br
a.
f.
Br
j.
g.
b.
k.
Cl
c.
h.
Cl
Cl
l.
Cl
d.
Br
e.
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i.
m.
F
F
3. Draw the following:
a. 2-methyl-1-butene
b. 3-ethyl-2,5-dimethyl-3-hexene
i.
(Z)-1-chloro-2-ethyl-3-methyl-1-butene
j.
(1E,3E)-1-chloro-3-ethyl-2,4-dimethylhex1,3-diene
c. 4-methyl-2-hexyne
k. (E)-1-chloro-3-ethyl-4-methyl-2-pentene
d. 1-chloro-2-fluorocyclohexene
l.
(Z)-4-ethyl-3,6-dimethyl-3-heptene
e. (Z)-3-methyl-2-pentene
m. (2E,4Z)-4-bromo-1-chloro-2-methyl-2,4hexadiene
f.
cis-1-chloro-1-butene
n. 3,6-dimethyl-3-propylhept-5-en-1-yne
g. trans-3-methyl-3-hexene
o. (2E,4Z)-3-bromo-2-chloro-5-propyl-4-tbutyloct-2,4-diene-6-yne
h. (Z)-2-bromo-3-methyl-2-pentene
4. Rank the following alkenes in order of increasing stability:
a.
b.
e.
c.
d.
5. Label the following species nucleophile or electrophile:
a. +NO2
c. H+
b. HC≡CH
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d.
+
NH4
e. Cl-
f.
–
OH
6. Classify (primary, secondary, etc.) the following carbocations and rank them in order of increasing stability:
+
+
c.
a.
+
+
d. CH3
b.
7. Draw all possible products for the following reactions and label each major/minor. Draw a complete mechanism for
at least one of each type of reaction.
a. 2-methyl-1-butene + HBr
b. Cyclohexene + HCl
c. Acid catalyzed hydration of 2-methyl-2-hexene
d. 2,4-dimethyl-2-heptyne +
e. 2-pentene + water + acid
f.
2-butyne + excess HCl
g. 1 mol 1-propyne + 1 mol HBr
h. 3-octyne + water + acid
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OH + H2SO4
8. Determine the best combination of reactants (and in what amounts, where applicable) to form the following
products:
O
a.
Cl
b.
Br
c.
F
F
d.
O
e.
HO
f.
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12.13.2012