You are on page 1of 1

bonding,

(2) molecular weight and surface area, and (3) dipole moments. Except for neopentane,
these compounds
have similar molecular weights. Neopentane is the lightest, and it is a compact spherical
structure that minimizes van der Waals attractions. Neopentane is the lowest-boiling
compound.
Neither hexane nor 2,3-dimethylbutane is hydrogen bonded, so they will be next higher in
boiling
points. Because 2,3-dimethylbutane is more highly branched (and has a smaller surface
area)
than hexane, 2,3-dimethylbutane will have a lower boiling point than hexane. So far, we
have
The two remaining compounds are both hydrogen-bonded, and pentan-1-ol has more area
for van der Waals forces. Therefore, pentan-1-ol should be the highest-boiling compound.
We
predict the following order:
10 C 58 C 69 C 102 C 138C
The actual boiling points are given here to show that our prediction is correct.
neopentane 6 2,3-dimethylbutane 6 hexane 6 2-methylbutan-2-ol 6 pentan-1-ol
neopentane 6 2,3-dimethylbutane 6 hexane 6 the others

PROBLEM 2-17

For each pair of compounds, circle the compound you expect to have the higher boiling
point.
Explain your reasoning.
(a) and
(b) and
(c) or
(d) and
(e) and
(f)
1CH3CH2CH2 1CH3CH223N 22NH
1CH32HOCH21CH2 3CCH1OH2CH3 24CH2OH
CH3CH2OCH2CH3 CH3CH2CH2CH2OH
CH31CH22CH3 5CH2OH 1CH226CH3
1CH322CHCH2CH2CH1CH322 1CH323CC1CH323
C
CH3
CH3
CH3 CH3
neopentane
hexane
2,3-dimethylbutane

OH

pentan-1-ol

OH
2-methylbutan-2-ol

Application: Biochemistry
Hydrogen bonding is essential for the
structural integrity of many biological
molecules. For example, the double helix
structure of DNA is maintained, in part,
by hydrogen bonds between the bases:
adenine pairs with thymine and guanine
pairs with cytosine. Figure 23-25 shows
this base-pairing.

NH and NH2

Alcohols