ALDEHYDES AND KETONES
1. Give an IUPAC name of each of the following compounds:
a)
b)
c)
d)
e)
O
O
O
O
CHO
O
OH
CH3
CH3
NO 2
2. Write the structures:
a) 4-methyl-2-pentanone
b) benzyl ethyl ketone
c) dibenzyl ketone
d) acetophenone
e) benzophenone
f) acetone
3. Predict the product of reaction of butanal with:
a) LiAlH4
g) aniline
b) NaBH4
h) dimethylamine / H+
c) H2/Pt
i) hydroxylamine
d) 1) CH3MgI 2) H3O+
j) Ag2O
e)
k) H2CrO4
1) H C C Na
2) H3O+
l) hydrazine 1 mol and 0.5 mol
m) sodium cyanide
f) methanol / HCl (g)
4. Repeat the preceding problem for cyclohexanone from a) to m).
5. What is the principal product in each reaction?
a)
b)
CHO
OH
CHO
Ag2O
H3CO
NaOH
O
PTSA
OCH 3
OCH 3
c)
OH
d)
CHO
O
OCH 3
CH 3ONH 2
H
N
O
OH
e)
O
O
HCl, H 2O
heat
1
H+
heat
6. Using ethanol as the source of all the carbon atoms, describe efficient syntheses of each of
the following, using any necessary organic and inorganic reagents.
a)
O
O
O
O
b) H
d) 3-butyn-1-al
CH 3
e) acetaldehyde diethyl acetal
c) 1-butanol
f) 3-butyn-2-ol
7. The following five-step synthesis has been reported in the chemical literature. Suggest
reagents appropriate for each step.
O
O
O
O
O
O
O
OH
O
O
H
O
CH 3
O
CH 3
O
O
O
O
8. Synthesis of each of the following compounds have been reported in the chemical
literature. Using the indicated starting material and any necessary organic or inorganic
reagents, describe short sequences of reactions that would be appropriate for each
transformation.
Ph
Ph
a)
from
O
CH 3
b)
1,1,5-trimethylcyclononane from 5,5-dimethylcyclononanone
CH 3
c)
from o-bromotoluene and 5-hexenal
Cl
d)
CH 3
O CH 3
from 3-chloro-2-methylbenzaldehyde
2