Review Worksheet for Exam 3 (Chapter 14)
Chem 102, Fall 2005
(Not Graded)
1. Give the name for each of the following structures:
2. Draw the structure for each of the following names:
a) 2-propanol
b) 2-methylcyclobutanol
c) 3-ethyl-2-hexanethiol
d) 2,4-diaminophenol
e) methyl phenyl ether
f) furan
g) 3-ethyltetrahydropyran
h) ethylene oxide
i) anisole
3. Give the major product for each of the following reactions (use NR for no reaction):
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.
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 H-bond with itself than does cyclopentanol.
7. Rank the following compounds in order of increasing boiling point (number 1-4 = lowest to highest):
8. Circle the compounds that are soluble in water. Include those that are only slightly soluble.
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.
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.
11. Write the arrow-pushing mechanism for the reaction in part a of question 3: