CHEMISTRY 122
HW CH#5 ALCOHOLS
10, 11, 13, 16, 19, 22, 24, 29, 32, 33, 37, 39, 60, 62.
5-10
Compounds (c) and (d) are secondary alcohols
OH
OH
(c)
(d)
two non-hydrogen groups attached to
the carbon bonded to the hydroxyl
5-11
None
5-13
two non-hydrogen groups attached to
the carbon bonded to the hydroxyl
5-16
(a) Prednisone contains three ketones, one primary alcohol, one tertiary alcohol,
one disubstituted carbon-carbon double bond, and one trisubstituted carboncarbon double bond.
(b) Estradiol contains one secondary alcohol and one disubstituted phenol.
5-19
As the molecular weight of an alcohol increases, the hydrocarbon part of the
molecule becomes larger and larger, thus increasing the surface area. The physical
properties of alcohols, including their solubility in water, then become more like those of
hydrocarbons of similar carbon skeletons. In other words the polarity decreases and
solubility decreases.
5-22
In order of increasing boiling point, they are:
CH3CH2CH3
CH3CH2OH CH3CH2CH2CH2OH
HOCH2CH2OH
-42 C
78 C
117 C
198 C
d<c<a<c
5-24
The cooling effect comes from evaporation. 2-Hexanol's boiling point is too high
to be easily evaporated from the skin.
5-29
a. T b. T c. T d. F e.T f.F g. T h. F i. T j. F
5-37
a. H2SO4
f. H2/Pt
b. HOH/ H2SO4
g. K2Cr2O7/ H2SO4
c, K2Cr2O7/ H2SO4 d. HBr e. Br2
h. PCC
i. K2Cr2O7/ H2SO4
5-39
Ethyl alcohol, found in alcoholic beverages and used as a solvent
Ethylene glycol, found in antifreeze
5-40
Isopropyl alcohol, used medicinally as a disinfectant
Isopropylene glycol, used as a solvent
5-60
The electronegativity difference between N and H is less than the
electronegativity difference between O and H; therefore, the O-H bond is more
polar than a N-H bond. Using this information, a N-H----N hydrogen bond is
weaker than an O-H----O hydrogen bond.
5-62
The five ether constitutional isomers with molecular formula C5H12O and their
common names are:
O
O
Butyl methyl ether
O
tert-Butyl methyl ether
O
Isobutyl methyl ether
O
Ethyl propyl ether
sec-Butyl methyl ether
O
Ethyl isopropyl ether