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CHEM 10052
Problem Set #2
Name_____________________
1. Compare the structure and physical properties of alcohols with ethers.
2. Compare the structure and physical properties of aldehydes with ketones.
3. Name the following compounds using either IUPAC or common nomenclature.
CH3CH2
HO
a)
CH3
H
CH3
c)
Cl
OH
CH3
O
CH3
CH3
b)
OH
SH
CH3
OH
CH3
d)
CH3
e)
Br
f)
OH
2
Br
CH3
O
O
C
g) CH3CH2CH2
CH3
CH3 CH2
H
CH3
h)
i)
CH3
OH
CH3 CHCH3
NO2
j)
k)
Cl
4. Write structural formulas for each of the following:
a) 2-butanone
b) 3-methylcyclopentanone
c) acetone
d) 2-propanol
e) 2-chloro-3-hexanol
f) 2-ethoxypentane
g) trans-3-bromocyclopentane thiol
h) 1-bromo-2-methyl-3-heptanone
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5. Write a general mechanism for dehydration of alcohols.
6. Write a general mechanism for the aldol condensation.
7. Predict the products for the following reactions. Indicate major and minor products
where appropriate.
O
+ HOCH 2CH 2CH2 OH
a)
H+
O
b) CH3
C
[R]
H
c) CH3CH2CH2OH
[O]
OH
CH3
d)
e) CH 3OH
f)
H2SO4

Na
CH 3 CH 2 CH 2 Br + CH 3 O - K +
4
O
g) CH3
[O]
C
H
O
cat. NaOH
C
h)
CH3 CH2
H
i)
CH3CH2CH2SH
CH3
[O]
+
H2O, H
j)
Br 2
j)
FeBr 3
H2 SO4
HNO 3
k)
H2 SO4
SO 3
i)
8. Provide the missing reagents needed for the following reactions:
O
CH3CH2CH2OH
a)
CH3CH2
H
O
C
b) CH3CH2
H
c) CH 3CH 2CH 2OH
CH 3CH 2CH 2OH
-
CH 3CH 2CH 2O Na
+
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9. a. Give the sequence of oxidation for organic molecules starting with alkanes.
b.
Show the structural formulas for each of the intermediate compounds formed as
methane is completely oxidized (i.e. through the oxidation sequence).