Download 102 Rev wkt ex3 key Fall05

Review Worksheet for Exam 3 (Chapter 14)
Chem 102, Fall 2005
(Not Graded)
1. Give the name for each of the following structures:
OH
OH
a)
b)
c)
SH
F
3-ethyl-2-hexanol
3-fluorocyclopentanol
2-methyl-3-pentanediol
OH
d)
e)
2,4-dimethylphenol
O
f)
diethyl ether
OH
HO
1,2-ethanediol
Cl
O
O
g)
h)
i)
O
O
4-methyl-2-methoxypentane
tetrahydrofuran (THF)
4-chloro-1,3-dioxane
O
j)
k)
l)
O
2,3-dimethylethylene oxide
3-cyclopropylfuran
2. Draw the structure for each of the following names:
a) 2-propanol
OH
O
4,4-dimethyltetrahydropyran
b) 2-methylcyclobutanol
OH
CH3
c) 3-ethyl-2-hexanethiol
SH
d) 2,4-diaminophenol
OH
H 2N
e) methyl phenyl ether
O
f) furan
O
g) 3-ethyltetrahydropyran
O
h) ethylene oxide
O
i) anisole
O
NH2
3. Give the major product for each of the following reactions (use NR for no reaction):
H3O+
OH
a)
Heat
b)
H3O+
OH
2
O
Heat
H
PCC
OH
c)
O
OH
O
PCC
d)
H3O+
OH
O
H3O+
OH
PCC
g)
2
I2
SH
OH
i)
O
CrO3
f)
h)
OH
CrO3
OH
e)
NR
S
S
O
+
H 2O
+
H3O+
4. Write and balance the combustion reaction for each of the following alcohols and
ethers:
a) dipropyl ether
C6H14O + 9O2  6CO2 + 7H2O
b) 2-pentanol
2C5H12O + 15O2  10CO2 + 12H2O
c) phenol
C6H6O + 7O2  6CO2 + 3H2O
5. Which has the higher boiling point, ethanol or ethanethiol? Explain, using drawings
to illustrate your answer.
Ethanol has the higher boiling point because it can H-bond with itself, while ethanethiol
can’t. The S-H bond is not polar enough for H-bonding.
HO
HS
Vs.
OH
SH
No H-bonding
HO
6. Which has the higher boiling point, cyclopentanol or 1,3-cyclopentanediol? Explain,
using drawings to illustrate your answer.
1,3-cyclopentanediol has the higher boiling point because it has more positions to Hbond with itself than does cyclopentanol.
OH
OH
Vs.
OH
Has 4 H-bonding positions
Has two H-bonding positions
7. Rank the following compounds in order of increasing boiling point (number 1-4 =
lowest to highest):
OH
O
3
2
OH
HO
O
4
1
8. Circle the compounds that are soluble in water. Include those that are only slightly
soluble.
OH
OH
OH
HO
O
OH
OH
O
O
O
OH
9. Tetrahydrofuran is soluble in water but cyclobutane and cyclopentane are not.
Explain, using drawings to illustrate your answer.
Tetrahydrofuran (THF) can H-bond with water, while the cycloalkanes can not.
O
H
O
O
H
H
Vs.
H
No H-bonding
10. Phenol is soluble in water, but anisole is not. Explain, using drawings to illustrate
your answer.
Phenol is a weak acid and can partially ionize in water. Anisole is an ether with 6
carbons. Ethers can not ionize in water.
O
O
H
+
H 2O
+
H 3O
Vs.
O
+
H 2O
No reaction
11. Write the arrow-pushing mechanism for the reaction in part a of question 3:
H
O
+
O
+
O
H
H
H
H
OH
H
H
H
H
O
+
H
O
H
H
H
+
H
+
O
H
H
O
H
H