Chemistry 1152
Review for Exam I — Answers – Part I
CH3
1. CH3CH2CH2CH2CH2CH3
CH
CH2
Hexane
H3C
CH2
H3C
CH2
CH3
3-methylpentane
2-methylpentane
C
CH2
CH3
CH3
CH3
H3C
CH2
CH
CH3
CH3
CH3
CH
H3C
2,2-dimethylbutane
CH
CH3
CH3
2,3-dimethylbutane
2. a. CH4
b. CH3CH2CH2CH3
d.
H3C
CH3
cyclobutane
c.
CH3
CH
CH2
CH2
CH2
CH3
2-methylhexane
There are other
possible answers
for this question.
methylcyclopropane
3.
CH3
H3C
CH
No number is needed as there is only one possible position
for it. (The number 2 position.)
CH2
CH3
methylbutane
4. All combustion reactions give carbon dioxide and water (CO2 + H2O). If there is a
deficiency of oxygen, CO or C could be formed instead.
5. Alkanes are non-polar organic compounds. Water is a polar compound. Since “Like
Dissolves Like,” we would never have expected that the two should mix.
6.
a.
b.
c.
d.
e.
f.
2-bromo-3-ethyl-3-methylpentane
3-methylhexane
5-chloro-4-ethyl-2,3-dimethylheptane
3,5-dimethyl-6-propyldecane
3-bromo-1-chloro-2-iodopropane
1-chloro-2,3-dimethylpentane
g. 3-ethyl-2,6-dimethylheptane
h. 2,3-dimethylhexane
i. 4-ethyl-5-methylnonane
j. 1,1-dichloropropane
Cl
7. (a)
CH
CH2
CH3
CH3
C
Br
C
CH2
C
H3C
H3C
CH2
CH2
1-bromo-2-chloropentane
CH3
CH
CH3
CH3 H2C
CH3
CH2
CH3
5-ethyl-2,2,3,3,4,4-hexamethyloctane
CH3
(c)
CH3
(b)
H2C
I
C
CH2
Br
CH
CH
CH
H3C
(d)
CH
CH2
CH2
CH3
I
CH3
CH3
6-bromo-2,2-diiodo-3,5-dimethyl-4-propylnonane
CH3
(e)
Cl
CH
CH3
I
CH
CH2
Cl
(h) H3C
CH2
C
CH2
CH2
Cl
Cl
(g)
Cl
C
CH
C
Cl
CH3
Cl
tetrachloromethane
Br
CH3
Cl
1,3-dichloro-2-methylbutane
CH
CH2
CH3
CH3
4-ethyl-2,4-dimethylheptane
C
CH2
CH2
H3C
CH3
(f)
H3C
CH3
CH3
4-bromo-4-chloro-1-iodo-2,2,3-trimethylpentane
CH3
Br
Br
CH3
chloroethane
CH3
1,2-dibromo-3-methylcyclobutane
1,2-dimethylcyclohexane
(i)
(j)
8. CH2=CHCH3
9. (a)
CH3
CH
C
CH3
CH
C
H2C
(e)
C
CH3
CH3
Br
2,4,4-trimethyl-2-pentene
CH3
(g)
C
Cl
(h)
C
C
CH
CH
CH
CH3
CH2 C
C
C
H3C
CH3
CH3
1,2-dibromo-2-methylpropane
Cl
C
CH
H3C
CH2
Cl
1,1-dichloroethene
H3C
(f)
CH3
C
CH2
CH3
4-methyl-trans-2-pentene
CH3
Br
CH
CH
H3C
CH3
3,3-dimethyl-1-butene
(d)
Cl
CH3 (c)
(b)
CH2 CH3
2-chloro-6,6-dimethyl-4-octyne
CH3
(i)
H2C
CH3
CH3
Cl
H3C
4-chloro-4-methylhept-5-ene-2-yne
Cl
m-dichlorobenzene
CH2 CH3
(j)
Cl
CH2
p-chloropropylbenzene
10.
a. 2,4-dimethyl-2-hexene
b. cyclohexene
c. chloroethene
d. 2-bromo-2,6,6-trimethyl-4-nonyne
e. 3-methyl-1-butene
f. 4-ethyl-3-methyl-3-heptene
g. 3-bromocyclopentene
h. 7-iodo-4-methyl-2-heptene
i. heptane
1-ethyl-2-methylbenzene
j. 2-methylbutane
k. cyclohexane
l. methylbenzene (toluene)
m. 2-ethyl-1,3-dimethylbenzene
n. bromomethane
o. 1,4-dichlorobenzene or p-dichlorobenzene
p. 3,5-dinitro-1-propylbenzene
q. methylcycloheptane
r. 3-methyl-1-butyne
s. 3-phenylhexane
11. Add Br2. If the red-brown color of the Br2 disappears immediately, the compound
was the alkene, 2-butene. If the color remains, or lingers only to fade in the light,
it was the alkane, butane.
12. No, both would react in the same fashion.
λ
13. CH3CH2CH3 + Cl2
CH3CH2CH2—Cl + HCl
Alkane substitution reactions require heat or ultraviolet light and produce a byproduct.
Cl Cl
CH2=CHCH3 + Cl2
CH CH3
H2C
Alkene addition reactions are immediate without a catalyst and there is no byproduct.
14.
a.
b.
c.
d.
3-methyl-4-octene
cyclopentane
2-pentene
1-pentene
15. (a) H C
3
CH3
(b)
H3C
ethylcyclopentane
H2C
Br
H3C
C
CH3
CH
CH2
(d)
Cl
(c)
methylbenzene
(e)
CH2
3-bromo-2-ethyl-1-butene
Cl
C
H
CH3
CH2
2-chloro-4-methylhexane
Cl
CH CH3
CH
CH2
C
H
cis-1,2-dichloroethene
16.
(a) B. It has the longest carbon chain
(b) A & D and C, E
(c) E. Markovnikov’s rule does not apply.
(d)
H3C
CH2 CH3
C
H3C
H
C
C
C
H
H
H
cis-2-pentene
CH2 CH3
trans-2-pentene
17.
(a)
+ Br2
Br
CH3
(b)
H3C
CH2 CH CH2 CH3
Br
CH3
h

+ Cl2
H3C CH2 CH CH2 CH2
Cl
(c)

CH3CH3 + Cl2
CH3
(d)
H3C
C
CH
+ H2
CH3
H3C
Cl
CH2
Pt
+ HCl
CH3
H3C CH CH2
CH3

(e)
+ HCl
No Reaction

(f)
CH3
(h)
CH3CH=CH2 + H2
+ O2
CO2 + H2O
Ni
CH3CH2CH3
Br
(i)
H3C CH2
CH CH
CH3
C
CH3
CH3
+ HBr
H3C CH2 CH CH2 C CH3
CH3
CH3
Pt
(j)
+ H2
CH3
CH3
Cl
(k)
+ HCl
CH3
CH3
(l)
Cl
+ Cl2

(m) CH3CH2CH2CH2CH2CH2CH3 + O2
CH2 CH CH2
(n)
Cl
CO2 + H2O
CH2 CH CH2
+ Cl2
Cl
CH3
(o)
Fe
Cl
CH3
+ Br2
Br
H3C
(p)
CH3
CH3
C
+ HCl
C
C
H
H3C
CH3
H3C
CH2
Cl
Fe
(q)
SO2OH
+ H2SO4
OSO2OH
(r)
CH3
CH3
+ H2SO4
COOH
CH3
(s)
+ KMnO4
COOH
CH2 CH3
CH3
(u)
+ Br2
h

CH2
Br
Cl
CH CH3
H3C
(v) CH2=CHCH3 + HCl
CH3 Br
CH3
(x)
H3C C C
CH3
CH
+ Excess HBr
C
H3C C
CH3 Br
CH3
CH3
(y)
(z)
H3C
C
CH3
CH3
+ HCl
CH CH CH3
No Reaction
+ O2

CO2 + H2O
O
(aa) CH3CH=CHCH3 + O3
H3C
C
H
O
O
(bb) CH3CH=CHCH2CH3 + O3
H3C
+
C
H
Br
Cl
(dd)
H3C CH2 C
H
Cl
+ Excess HBr
Br
CH3
CH3
Cl
(ee) CH3CH=CHCH2CH3 + HCl
Cl
or
H3C CH CH2 CH2 CH3
H3C CH2 CH CH2 CH3
Chemistry 1152
Review for Exam I — Answers – Part II
1.
a)
b)
c)
d)
e)
2,2-dimethyl-1-butanol
2-ethyl-1-pentanol
ethyl methyl ether (common) or methoxyethane
4-bromo-3methyl-1-butanol
5-chloro-4-ethyl-6-methyl-3-propyl-1-octanol
OH
H3C
CH
CH2
CH3
CH3
OH
H3C
2. a)
H2
C
b)
C
H3C
CH3
C
H2
CH2
HO
c)
Cl
CH
d) CH3-O-CH3
OH
i)
OH
OH
j)
HO CH3
H3C
H3C C
CH
CH3
CH3
CH2 CH2 CH3
3. Methane is a low molecular weight alkane, very non-polar, and is expected to be a
gas. Methanol has a polar alcohol (-OH) functional group and can
undergo hydrogen bonding so it remains in the liquid state longer.
5. a) same
b) isomers
c) isomers
d) isomers
e) isomers
CH3
H3C
8.
CH2
CH2=CH2 + H2O
OH
H3C
O
CH2
KMnO4
H3C
OH
C
OH
Intramolecular
10.
CH3CH=CH2 + H2O
H2SO4
CH3CH2CH2-OH
Intermolecular
CH3CH2CH2-O-CH2CH2CH3
+ H2 O
CH3
HO
12.
CH2
OH
OH
H3C
CH2
ethanol
C
H3C
2-phenyl-2-butanol
cyclohexanol
H2SO4
13.
CH2=CH2 + H2O (Intramolecular)
OH
H3C
CH2
OH
H2SO4
H2SO4
H2SO4
CH3CH2-O-CH2CH3 + H2O
(Intermolecular)
+ H2O (Intramolecular)
O
(Intermolecular)
+ H2O
CH3
CH3
13.
HO
H2SO4
C
C
+ H2 O
CH
CH2
(Intramolecular)
H3C
H3C
CH3
H3C
H2SO4
C
+ H2O
(Intermolecular)
C
O
CH2
H2C
H3C
CH3
O
14.
OH
H3C
KMnO4
CH2
H3C
C
OH
OH
KMnO4
O
CH3
HO
C
KMnO4
No Reaction
CH2
H3C
16.
b) CH3CH2OH
O
KMnO4
H3C
C
OH
O
CH3
KMnO4
CH2 CH
CH2
e)
C
CH3
OH
f) H3C
H2C CH3
CH2
CH2
CH OH
CH2
H3C
+ KMnO4
H2C
CH2
CH2
C
CH2
O
KMnO4
H3C C OH
H2SO4
Intramolecular
r) CH3CH2OH
CH2=CH2 + H2O
CH3CH2–O–CH2CH3 + H2O
H2SO4
Intermolecular
OH
CH
t) CH2=CHCH3 + H2O
u) (CH3)3C—OH
v) CH3OH
KMnO4
H2SO4
OH
y)
H3C
CH3
No Reaction
CH3–O–CH3 + H2O
KMnO4
O
CH3
O
z) CH3CH2—O—CH3 + O2
Δ
CO2 + H2O
19.
If intramolecular
H2SO4
e)
CH CH2
CH2 CH2 OH
If intermolecular
CH2 CH2 O CH2 CH2
KMnO4
f) H3C CH2 CH CH2 CH3
OH
H3C CH2 C CH2 CH3
O
CH3
k)
H3C CH2 CH2 C
CH3
OH
KMnO4
No Reaction
Intermolecular
m)
H3C CH O
CH3
CH3
H2SO4
H3C
CH3
+ H2O
CH OH
Intramolecular
CH3
q)
CH CH3
C
H2C
H3C CH CH2
KMnO4
OH
CH3
No Reaction
+ H2O
CH3
r) H3C
20.
C CH2 OH
CH3
CH3
H2SO4
H3C
CH3
Intermolecular
only
C CH2 O CH2 C CH3
CH3
CH3
There is usually more than one correct answer for the
following:
b)
CH3CH=CH2 + H2O
c)
OH
H3C CH CH3
Δ
OH
H3C CH CH3
O
H3C C
KMnO4
CH3
H2SO4
d)
OH
O
Intermolecular
O
e)
CH3CH2CH2CH2OH
KMnO4
H3C
C
CH2
CH2
OH