Chemistry 1152
Review for Exam I – Part I
1. Draw all the isomers of C6H14. Can you name them?
2. Write structural formulas for: a. methane b. butane
C4H8 (saturated structure)
c. an isomer of heptane
d.
3. Draw a structure for methylbutane. Why is there no number listed indicating the position
of the methyl group?
4. What are the products of a combustion reaction? Under what conditions would those
products be different?
5. Why do alkanes have low solubilities in water? Did you expect this?
6. Name the structures below.
(a)
(b)
CH3
Br
H3C
CH2
H3C CH C
CH2
CH
CH3
H2C
CH3
CH2
CH2
CH3
CH3
H2C
H3C
(c)
H3C
CH3
CH CH CH CH2 CH3
CH
CH3
(d)
H3C
Cl
CH2 CH2 CH
H2C
CH3
CH
H2C
CH2 CH
CH2 CH2 CH3
CH3
(e)
Cl CH2 CH CH2 Br
(f)
H3C
CH2 CH
CH CH3
CH2
Cl
I
(g)
H3C
CH3
CH
H2C
CH2 CH2 CH
CH3
CH CH3
CH3
CH3
(h)
H3C CH2 HC
H2C
CH
CH3
CH3
CH3
CH3
Chemistry 1152
H3C CH2 CH2
(i)
H2C
Page 2
H2C CH3
CH CH CH2 CH2 CH3
(j)
H3C CH2 CH Cl
Cl
CH3
7.
Draw correct structures for…
a. 1-bromo-2-choloropentane
b.
5-ethyl-2,2,3,3,4,4-hexamethyloctane
c. 6-bromo-2,2-diiodo-3,5-dimethyl-4-propylnonane
d.
4-ethyl-2,4-dimethylheptane
e. 1,3-dichloro-2-methylbutane
f.
4-bromo-4-chloro-1-iodo-2,2,3-trimethylpentane
g.
tetrachloromethane
h.
chloroethane (Why no number?)
i.
1,2-dimethylcyclohexane
j.
1,2-dibromo-3-methylcyclobutane
8. The compound C3H6 has at least two isomers. One is an alkene while the other is a
saturated hydrocarbon. Draw the structures.
9. Draw correct structures for…
a. 3,3-dimethyl-1-butene
b.
4-methyl-trans-2-pentene
c. 1,1-dichloroethene
d.
1,2-dibromo-2-methylpropane
e. 2,4,4-trimethyl-2-pentene
f.
2-chloro-6,6-dimethyl-4-octyne
g.
4-chloro-4-methylhept-5-ene-2-yne (***Try this one***)
h.
m-dichlorobenzene
i.
1-ethyl-2-methylbenzene
j.
p-chloropropylbenzene
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10. Write correct systematic names for…
(a)
H3C
CH CH C
CH2
CH3
CH3
(b)
H2C
CH
(b)
CH3
CH3
(d)
H3C
Cl
C
CH3
CH2
C
C
CH3
H3C
CH
CH
(f)
CH2
CH2 CH2 CH3
CH3
Br
(c)
C
H3C CH2 C
H3C
C
CH2 CH3
H2C CH2 CH3
(d)
(h) H C
3
Br
CH CH CH CH2 CH2 CH2
I
CH3
(i)
(CH3)2CHCH2CH3
(j)
CH3(CH2)5CH3
(k)
CH3
CH3
(l)
(m)
CH2 CH3
(n)
H3C Br
CH3
Cl
H2C
(o)
CH2
CH3
(p)
Cl
(q)
NO2
CH3
(r)
HC
C
CH
CH3
NO2
(s)
CH3
H3C
CH2 CH
CH2 CH2 CH3
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11. Describe a simple chemical test that could be used to distinguish between 2-butene and
butane. Describe what you would do and what you would see.
12. Would the test you described in #11 be useful to test between 2-butene and 1-butene?
13. Both propane and propene react with chlorine. These reactions require different
conditions and produce different products. Explain.
14. Write correct systematic names for…
(a) H3C
CH2 CH2 CH CH CH CH2 (b)
CH3 CH3
(b) H3C
CH
CH
CH2 CH3
(d)
H2C
CH CH2 CH2 CH3
15. Draw correct structures for…
a.
ethylcylcopentane
b.
methylbenzene
c.
2-chloro-4-methylhexane
d.
3-bromo-2-ethyl-1-butene
e.
cis-1,2-dichloroethene
16. Consider the following molecules…
(a) CH3CH2CH2CH2CH3
(d)
(c)
(e) CH3CH=CHCH2CH3 (f) CH2=CHCH2CH2CH3
CH3
H3C
(b) CH3CH2CH2CH2CH2CH3
C
CH3
CH3
(a) Which do you think has the highest boiling point?
(b) Which molecules, if any, are isomers of one another?
(c) Which molecule(s), if any, would add HCl to yield two different products?
(d) Draw the cis- and trans- isomers of compound E.
17. Complete the following reactions… If no reaction occurs, write “NO REACTION.”
(a)
+ Br2
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CH3
(b)
H3C
(c)
CH3CH3 + Cl2
(d)
CH2 CH CH2 CH3
CH3
H3C
C
(e)
h

Pt
+ H2
CH
CH3
+ HCl
(f)
CH3
(h)
CH3CH=CH2 + H2
(i)
+ Cl2
H3C CH2
CH CH
CH3
+ O2
Pt
C
CH3
CH3
+ HBr
Pt
(j)
+ H2
CH3
(k)
(l)
+ HCl
CH3
+ Cl2
(m) CH3CH2CH2CH2CH2CH2CH3 + O2

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(n)
+ Cl2
CH2 CH CH2
FeBr2
CH3
(o)
+ Br2
H3C
(p)
CH3
C
+ HCl
C
H
H3C
(q)
+ H2SO4
H2SO4
(r)
CH3
+ H2O
CH3
(s)
+ KMnO4
CH2 CH3
CH3
(u)
+ Br2
(v) CH2=CHCH3 + HCl
CH3
(x)
H3C C C
CH3
CH
+ Excess HBr
h

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CH3
(y)
(z)
H3C
C
CH3
CH3
+ HCl
CH CH CH3
+ O2
(aa) CH3CH=CHCH3 + O3
(bb) CH3CH=CHCH2CH3 + O3
Cl
(dd)
+ Excess HBr
CH3
(ee) CH3CH=CHCH2CH3 + HCl

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Chemistry 1152
Review for Exam I – Part II
1. Write systematic names for the following:
CH3
CH3
a)
C
H3C
CH2
H2C
b)
OH
CH
CH2
CH2
H3C
CH3
CH2
OH
CH2
CH3
c) H3C
CH2 O
d)
CH3
Br
CH
CH2
CH2
CH2
CH3
e)
CH3
H2C
CH
H3C
CH2
CH
OH
CH2
CH
CH
Cl
H2C
CH2
CH2
CH3
2. Draw structures for the following…
a. 2-butanol
b. 2-chloro-2-propanol
c. 2-methyl-1-pentanol
d. dimethyl ether or methoxymethanol
i. 3-propylphenol
j. a primary, secondary and a tertiary alcohol
3. Why is methanol a liquid at 25C while methane is a gas?
OH
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5. Explain whether the molecules pictured here are the same, isomers or totally unrelated.
a)
CH2
O
and
O
C
C
H3C
CH2
CH3
HO
OH
O
O
b)
and
HC
H3C
CH2 C
O CH2 CH3
OH
O
H2C
c) H3C CH2 CH2 C
O CH2
and
OH
and
HO
CH2 CH CH CH2
OH
CH3
O
d) H3C CH2 CH2 C
O CH2
OH
CH3
O
O
C
e) H3C CH2 C
and
O
H3C
CH2 O
8. Prepare ethanol from ethene. Then convert the ethanol to ethanoic acid.
d. a tertiary alcohol
e. a phenyl ester
10. Using any primary alcohol, write the reactions for both intramolecular and
intermolecular dehydration. Name the products formed.
12. Draw a primary, secondary & tertiary alcohol. Name them.
13. React each of your alcohols from #12 with H2SO4.
CH2
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14. React each of your alcohols from #12 with KMnO4.
16. Complete the following reactions. If no reaction occurs, write “NO REACTION.”
KMnO4
b) CH3CH2OH
CH3
CH2 CH2 CH
e)
f)
H3C
CH3
H2C CH3
CH2
CH2
CH OH
CH2
+ KMnO4
KMnO4
H2SO4
Intramolecular
r) CH3CH2OH
H2SO4
Intermolecular
t) CH2=CHCH3 + H2O
u) (CH3)3C—OH
v) CH3OH
KMnO4
H2SO4
KMnO4
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OH
KMnO4
y)
z) CH3CH2—O—CH3 + O2
Δ
19. Complete these reactions, as always, if no reaction occurs, write NO REACTION.
H2SO4
e)
CH2 CH2 OH
f)
H3C CH2 CH CH2 CH3
OH
180 °C / 140 °C
KMnO4
CH3
k) H3C CH2 CH2 C
CH3
OH
KMnO4
Intermolecular
CH3
m)
H3C
180 °C
H2SO4
CH OH
Intramolecular
140 °C
Chemistry 1152
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CH3
C
q)
H2C
CH3
r) H3C
C CH2 OH
CH3
KMnO4
OH
CH3
H2SO4
140 °C
20. For each of the following reactions, you supply the reactants and conditions necessary to
produce the indicated product. (these will not be on the test but would be good practice to
make sure that you know your reactions.)
OH
H3C CH CH3
b)
c)
O
H3C C
d)
O
CH3
O
e)
H3C
C
CH2
CH2
OH