1
CHEM 10052
Supplemental Problems
1) Compare the physical properties of alkanes, alkenes, alkynes and aromatic hydrocarbons.
Include descriptions of reactivity, melting points, boiling points, and water solubility.
See notes
2) Name twelve different functional groups and draw structural formulas for representative
examples of each functional group class.
See notes
3) Draw orbital diagrams for alkenes and alkynes. Indicate the type of orbital hybridization,
molecular geometry, bond angles, and the  and  bonds in each diagram.
See notes
4)
a. Draw structural formulas for four different isomers that have the formula C 6H12.
CH3CH2CH2CH2
H
C
C
H
CH3CH2
C
CH3CH2CH2
CH3
C
H
C
H
H
CH3
C
H
CH3
b. Draw structural formulas for four different isomers that have the formula C 5H10O.
O
CH3CH2CH2CH2
CH3CH2
C
H
C
O
H
CH3CH2CH2
CH2OH
C
H
O
C
CH3
2
c. Draw structural formulas for four different isomers that have the formula C 4H8O2.
O
CH3CH2CH2
C
O
OH
C
CH3CH2
OCH3
OH
O
H
C
O
OCH2CH2CH3
5) Name the following compounds using either IUPAC or common nomenclature.
Br
CH3
Br
a)
b)
c)
1-methylcyclohexene
3-bromocylopentene
cis-1-bromo-3-chlorocyclopentane
CH3
CH3CH2CH2CH C
d)
C
CH3
Br Br
H C C Br
CH3 CHCHCH2 CH2 CH3
CH3
e)
4-methyl-2-heptyne
Cl
H H
f)
Br
3-bromo-2-methylhexane
1,1,2-tribromoethane
CH3 CH2
CH3
C
g)
h)
trans-3-methyl-2-hexene
H
g)
4-isopropylheptane
C
CH2 CH3
trans-3-methyl-3-hexene
6) Write structural formulas for each of the following:
a) 2,3-dimethylbutane
CH3
CH3
H
C C CH3
H
CH3
b) trans-1,3-dimethylcyclohexane
CH3
CH3
c) 2-methylheptane
CH3
CH3
C
H
CH2CH2CH2CH2CH3
3
d) cis-2-methyl-3-hexene
CH3
CH3CH2
e) 4-chloro-2-pentyne
CHCH3
C
H
CH3
C
C
C
H
H
C
CH3
CH3CH2CH3
Cl
g) trans-3-hexene
f) propane
h) 1,2,2-trinitropentane
O2 N
NO2
NO 2
7) Write a general mechanism for halogenation of alkanes.
See notes
8) Write a general mechanism for the hydration of propene. Explain why 2-propanol is the
major product.
See notes
9) Write a general mechanism for dehydration of alcohols.
See notes
10) Predict the products for the following reactions. Indicate major and minor products where
appropriate.
CH3
CH3
+
H2O, H
b)
OH
C CH3
H
OH
minor
major
a)
CH3
+
OH
CH3
H
H2SO 4

CH3
C
C
H
H
Br Br
+ excess Br 2
c)
h
Br
Br
Br
Br Br
Br
Br + 10 HBr
Br
4
CH3
CH3
C
d)
H
H
CH3
H
C
e)
CH3 CH2 CH CH3
Br Br
Br 2
C
H
OH
H2O
cat. H2SO 4
C
CH3
H
C
H
CH2
CH3
CH3
H2, Pt
f)
g)
excess
+ Br 2
h) C 6H 14 + O
Br
h
+ HBr
eV
CO2 + H2O
2
H2O
H+
+
OH
OH
minor
major
Cl
i)
Cl2
Cl
j)
11) Fill in the missing reagents for the following:
H2SO4, ∆
a)
CH 3CH 2CH 2CH 2OH
1-butene
H2, Pt
b)
OH
H2O
c)
H+
CH CH3
5
12) Write Lewis structures and at least one resonance form for each of the following. Assign
formal charges to each atom and circle the most stable resonance form where
appropriate.
a) HCNO
H C N O
H C N O
both equivalent
b) CO32-
O
O
C
O
O
O
C
O
O
O
C
O
all equivalent
c)
N3-
-2
N N N
N N N
O
C
O
C
d) HCOOH
H
O
H
H
O
H
13) Expand the following line structures.
O
a)
O
b)
H
H 3C
a)
H
C
C
O
H
C
C
C
H2
CH3
H
C
CH3
H
H
b)
C
C
C
C
H
C
C
O
c)
C
O
C
H
H
H3C
CH2CH3
C
C
H2
C
H C C O
c)
H
C
H2
H2
C
CH3
CH3
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14) Determine the oxidation numbers of each atom in the following:
a. H2SO4
H = +1
S = +6
O = -2
b. HNO3
H = +1
S = +6
O = -2
c. H3PO4
H = +1
P = +5
O = -2
d. CO2
C = +4
O = -2
e. CH3OH
C = -2
H = +1
O = -2
f) CH2O
C=0
H = +1
O = -2