380 Chapter 13

The third compound has the lowest C:O absorption hand because its resonance
contributor
with the C-0 single bond is the more stable that that of the second compound.
0- 0-
O+ C :0+
more stable less stable
c. !ecause al"#l groups are more electron-donating than a h#drogen$ the absorption
band for the
carbon#l group bonded to two relati%el# electron&withdrawing h#drogens has the
greatest
fre'uenc#$ while the absorption band for the carbon#l group bonded to two al"#l
groups has
the lowest fre'uenc#.
i ii i
(1. )thanol dissol%ed in carbon disul*de will show the o+#gen-h#drogen stretch at a
greater
wa%enumber because there is e+tensi%e h#drogen bonding in the undiluted alcohol$
and an
o+#gen-h#drogen bond is easier to stretch if it is h#drogen bonded.
((. a. !ecause o+#gen is more electroncgati%e than nitrogen$ the 0-, stretching
%ibration is
associated with a greater change in dipole moment.
-.. The 0-, group of a carbo+#lic acid can form both intermolecular and
intramolecular
h#drogen bonds$ while an alcohol can form onl# intermolecular h#drogen bonds.
Therefore$ the e+tent of h#drogen bonding is greater in a earbo+#lic acid$ and
h#drogen
bonded O, groups ha%e broader absorption bands.
(3. The absorption band at 1100 cm/1 would be le00 intense if it were due to a C-
&1 bond because a
smaller change in dipole moment is associated with a C-1 bond compared to the
change in
dipole moment associated with the stretch of a 23-0 bond.
(3. a. The absorption band at 1400 cm/1 indicates that the compound has a
carbon#l group.
The absence of an absorption band at 3300 cm/1 indicates that the compound is not
a
carbo+#lic acid.
The absence of an absorption band at (400 crn/l indicates that the compound is not
an
aldeh#de.
The absence of an absorption band at 1100 crn/l indicates that the compound is not
an ester or
an amide.
The compound$ therefore$ must be a "etone.