Welcome to SI for Chemistry 1220!
Thursday, October 04, 2012
OUtline
Review Chapter 22: Reactions and Nomenclature of Alcohols, Ethers, and Aldehydes.
Exercises
1) Answer the following questions as True or False
a. Alcohols have lower boiling points than hydrocarbons of comparable molecular
masses.
b. As the number of carbon atoms in an alcohol increases, the solubility in water
decreases.
c. Ethers are more water soluble than hydrocarbons of comparable molecular mass.
d. Dihydroxy alcohols are more water soluble than monohydroxy alcohols with the
same number of carbon atoms.
e. Tertiary alcohols are more easily oxidized than primary or secondary alcohols.
f. Alcohols with many carbon atoms are very water soluble.
g. Secondary alcohols are converted to ethers by oxidation.
h. Ethanol reacts with sodium to produce sodium ethoxide and hydrogen gas.
i. The reaction between CH3CH2ONa and CH3Br to form an ether is known as the
Williamson synthesis.
j. C5H12O can be either an aldehyde or a ketone.
k. Primary alcohols can be oxidized to aldehydes and then ketones.
2) Write the structural formula for the following compounds
hexanal
nonanal
3-hydroxypropanal
2,4,6-trichloroheptanal
2-methoxypropane
1-ethoxy-2-ethylcyclohexane
1,2-butanediol
3,5-dimethyl-1-heptanol
Isopropoxybutane
3) Dehydration of 3-hexanol yields a mixture of two alkenes.
a. Name and draw the structures of both products.
b. Indicate the major and minor product.
c. Repeat for 3-methyl-1-cyclohexanol.
4) Cortisol is an anti-inflammatory agent that also regulates carbohydrate metabolism. What
oxidation product is formed when cortisol is treated with K2Cr2O7?
cortisol
5) Complete the following reactions. Name all alcohols, aldehydes, and ethers.
O
[O]
CH3
OH
CH3
CH3
[O]
[O]
H3C
OH
CH3
H 2SO4 (conc.)

CH3
CH3CH2Br
Na
H3C
OH
CH3
O
H 2O, H +
O
CH3
CH3
OH