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Chapter 3 143
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37.
Because cyclohexane is a nonpolar compound, it will have the lowest solubility in the most polar solvent,
which, of the solvents given, is ethanol.
3 2 2 2 2
3 2
2 3
3 2
3 2 2 2 2 3
CH CH CH CH CH OH CH CH OCH CH CH CH OH CH CH CH CH CH CH
1-pentanol
diethyl ether
ethanol
hexane
38.
a.
OH
>
OH
O OH
OH
O
>
>
b.
HOCH
2
CH
2
CH
2
OH
7
CH
3
CH
2
CH
2
CH
2
OH
7
CH
3
CH
2
CH
2
CH
2
Cl
39.
Hexethal would be expected to be the more effective sedative because it is less polar than barbital since
hexethal has a hexyl group in place of the ethyl group of barbital. Being less polar, hexethal will be better
able to penetrate the nonpolar membrane of the cell.
40.
Start with the least stable conformer and then obtain the others by keeping the front carbon constant and
rotating the back carbon clockwise.
a.
H
H
CH
3
H
H
1
2
3
5 4
CH
3
CH
2
A
H
H
CH
2
CH
3
CH
3
H
H
B
CH
2
CH
3
H
CH
3
H
H
H
C
CH
2
CH
3
H
H
CH
3
H
H
D
H
CH
3
CH
2
CH
3
H
H
H
E
H
H
CH
3
H
H
F
CH
3
CH
2
b.