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Chemistry 1152
Review for Exam II
CH2 CH3
1. Write systematic names for the following:
a)
CH3
CH2
CH3
OH
C
CH2
CH3 CH2
e)
CH3
CH2
O
CH3
Br
CH2
CH3
O
CH3
OH
f)
CH3 CH2 CH CH CH CH CH2 CH2
CH2
CH2
(CH3)2CH C
OH
CH3
O
O
g)
CH3 CH2 CH2 CH2 O
OH
d) CH2 CH CH2 CH2 OH
CH3
Cl
CH CH2
b)
CH3
c)
CH2
C CH2 CH3
h) CH3(CH2)4 C
OH
2. Draw structures for the following…
a. 2-butanol
b. 2-chloro-2-propanol
c. 2-methyl-1-pentanol
d. dimethyl ether
e. phenyl acetate (phenyl ethanoate)
f. 3-chlorobenzoic acid
g. ethyl benzoate
h. 2-methylbutanoic acid
i. 3-propylphenol
j. a primary, secondary and a tertiary alcohol
k. the acid chloride of propanoic acid
3. Why is methanol a liquid at 25C while methane is a gas?
4. Suggest a simple way to separate methanol and hexane. These compounds have the
same boiling point.
5. Explain whether the molecules pictured here are the same, isomers or totally
unrelated.
O
a)
O
and
CH3 CH2 C
OH
C CH2 CH3
HO
Chemistry 1152
Exam II Review
Page 2
O
O
b) H C O CH2 CH3
and
CH3 CH2
O C
OH
O
and
c) CH3 CH2 CH2 C
CH2 CH2 CH
CH CH2
OH
OH
O CH2 CH3
CH2
O
and HO
d) CH3 CH2 CH2 C
OH
O CH2 CH3
O
O
e) CH3 CH2 C
and
O
C
CH3 CH2 O
6. Write the reaction for the saponification of a fat or an oil. Are the reactions different?
7. Convert an appropriate alcohol to pentanoic acid.
8. Prepare ethanol from ethene. Then convert the ethanol to ethanoic acid.
9. Draw structures of…
a. a wax
b. a soap
c. a fat or oil
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.
11. What are the products of the hydrolysis of a fat?
12. Draw a primary, secondary & tertiary alcohol. Name them.
13. React each of your alcohols from #12 with H2SO4.
14. React each of your alcohols from #12 with KMnO4.
15. Draw propyl pentanoate. Draw potassium propanoate.
16. Complete the following reactions. If no reaction occurs, write “NO REACTION.”
NaOH
Chemistry 1152
Exam II Review
Page 3
a) propyl benzoate
KMnO4
b) CH3CH2OH
O
c)
+ HCl
_
O Na+
CH3 CH2 CH2 C
d) CH3(CH2)6COOH + NaHCO3
CH3
CH2
e)
CH2
KMnO4
CH CH3
CH2 CH3
f) CH3 CH2 CH2 CH2 CH OH + KMnO4
O
g) CH3CH2CH2OH + CH3CH2CH2- C
H+
Δ
OH
h) methyl ethanoate + H2O
H+
Δ
O
+ NH4OH
i) CH3 C
OH
O
j)
+ CH3CH2OH
C
H+
Δ
OH
O
k)
+ NaOH
OH
CH3 CH2 CH2 C
l) Soap + HCl
O
m) CH3 CH2 CH2 C
+ CH3 CH2 CH2 CH2 OH
OH
CH3
CH3
C CH2
CH3
O
C
+ NH3
OH
H+

Chemistry 1152
Exam II Review
Page 4
n)
o)
Δ
Fat + NaOH
O
H+
p) CH3 C O
+ H2O

HCl
q) CH3COOH + NaOH
KMnO4
H2SO4
Intramolecular
r) CH3CH2OH
H2SO4
Intermolecular
O
s)
H
C
+ KOH
OH
t) CH2=CHCH3 + H2O
u) (CH3)3C—OH
KMnO4
H2SO4
v) CH3OH
CH3
O
w)
CH3
C
+
CH3
CH
OH
Cl
O
x)
C
CH3
O C CH3
CH3
OH
+ H2O
H+

Chemistry 1152
Exam II Review
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KMnO4
y)
z) CH3CH2—O—CH3 + O2
Δ
17. Draw structures for the following…
a) 5-chloro-3-methylhexanoic acid
b) pentyl pentanoate
c) methanoic acid
18. Name each of the following…
b) CH3 CH2 C
a) CH2 CH2 CH2 C
OH
Br
CH3
O
O
O
_
O K+
c) CH3 CH2 O
C
O
d) CH3 C CH2 C
e)
OH
CH3
CH3
CH3
O
CH3 CH2 CH2 CH CH2 CH2 CH CH2 CH C
OH
19. Complete these reactions, as always, if no reaction occurs, write NO REACTION.
Pt
a) Oil + H2
b) Oil + NaOH
Δ
H+
Δ
c) Oil + H2O
O
d) CH3 CH2 CH2 C
+ HCl
_
O Na+
H2SO4
CH2 CH2 OH
e)
f)
CH3 CH2
CH CH2 CH3
OH
O
C CH2 CH2 C
OH
KMnO4
O
+ Lotsa CH3CH2OH
OH
H+

Chemistry 1152
g)
h)
Exam II Review
Page 6
O
CH3 C
H+
+ CH3CH2OH

OH
i) HCOOH + NaOH
O
j)
H+
CH3 C
+ H2O

O CH3
CH3
k) CH3 CH2 CH2 C CH3
KMnO4
OH
O
l)
+ CH3OH
C
Cl
Intermolecular
CH3
m)
CH3
H2SO4
CH OH
Intramolecular
n) CH3(CH2)5COOH + NH3
NaOH
O
o)

CH3 CH2 C
O CH CH3
H2O, H+
CH3

p) Soap + HCl
CH3
q)
CH2
CH3
r)
KMnO4
C OH
CH3 C CH2 OH
CH3
CH3
H2SO4
Chemistry 1152
Exam II Review
Page 7
O
s)
+
C
HO
Cl
20. For each of the following reactions, you supply the reactants and conditions
necessary to produce the indicated product.
a)
CH3 CH2
O C
O
OH
CH3
b)
CH CH3
O
CH3
c)
C
CH3
O
d)
O
e)
CH3 CH2 CH2
21. Complete the following reactions…
H2SO4
KMnO4
CH3CH2OH
HCOOH, H+, Δ
ice
C
OH