CHM 112
1.
SPRING 2007
WORKSHEET FOR ALDEHYDES AND KETONES
Write the IUPAC name for each of the following compounds:
H2
C
H2
C
CH
H3C
CH 3
CH 3
C
CH 3
H2
C
O
C
H
CH
CH 3 H
2
C
C
H2
C
C
H2
CH 3
C
H2
O
CH 3
CH 3
O
3-methyl-2-hexanone
3-isopropyl heptanone
3, 3-dimethyl octanal
H2
C
H3C
H2
C
C
H2
C
O
O
C
H
3-cyclobutyl propanal
2.
H2
C
1-phenyl-2-butanone
Write the full or condensed structural formula for each of the following compounds:
2-ethyl cyclopentanone
2-chloro-3, 5-dimethyl heptanal
benzaldehyde
Cl
H2
C
CH 2
H3C
H
C
H
C
CH
CH 3
4-phenyl-2-octanone
O
C
H
CH 3
O
O
CH
CH
CH 3
3-hydroxy-butanal
OH
H
C
CH
O
H2C
C
H3C
C
H2
3.
H2
C
CH
C
H2
a.
Aldehydes, ketones, and alcohols all have oxygen in their structures. Explain
why the boiling points of alcohols are higher than the boiling points of corresponding
(about same molar mass) carbonyls.
Alcohols can hydrogen bond with each other because of the
H
H
O
C
CH
C
hydrogen has a slightly positive charge and the oxygen a
H C
C
C
H
H
slightly negative one. The hydrogens on aldehydes or
X
H
O
C
ketone are not significantly positive so there is no hydrogen
H C
C
H
bonding. Overcoming strong IMF’s like hydrogen bonding
requires more energy and therefore a higher boiling point.
2
3
3
2
H2
C
H 3C
2
OH
C
H2
O
CH 3
C
H2
2
HO
C
H2
3
b.
Why are aldehydes and ketones more soluble in water than corresponding ethers?
The aldehydes and ketones have an oxygen that is
more accessible to the hydrogens in water to form
hydrogen bonds. In an ether, the oxygen is less
accessible and so hydrogen bonding is not as easy
and therefore the molecule is less water soluble.
3-hexanone
4.
propoxypropane
Complete the following reactions with the most appropriate reactant(s) or product(s).
H2
C
H2
C
CH
H3C
H2
C
K2Cr2O7
CH 3
C
H2
H2
C
H3C
CH 3
C
C
H2
OH
O
H2
C
H3C
2+
Cu
H2
C
CH3
C
No reaction because a ketone cannot be
oxidized under these conditions
C
H2
O
KMnO4
O
OH
CH 3
CH 3
CH 3
H2
C
H3C
H2
C
O
C
C
H2
CH 3
Cu2+
CH 3
C
H
H3C
C
C
H2
O
C
CH 3
OH
CH 3
H2
C
H3C
CH 3
C
H
H3C
C
C
H2
H 3C
CH 3
OH
OH
CH 3
C
H2
CH 3
H2
C
O
C
C
C
H2
[H]
CH 3
H2
C
H2
C
O
C
C
H2
CH 3
[H]
H3 C
O
C
C
H2
CH 3
C
H