Dr. Caroline Clower
Chemistry 2412
Aldehydes and Ketones
1. Name the following compounds
CHO
(a)
(R)-3-hydroxy-2-methylpropanal
H
H3C
CH2OH
O
(b)
2-methyl-3-pentanone
CHO
(c)
(d)
(2S)-2-ethyl-3-methylpentanal
O
CH3
(R)-3-methylcyclopentanone
2. Draw structures for the following compounds.
(a) 5-oxohexanal
O
O
H
O
(b) 3-methyl-3-buten-2-one
(c) isopropyl methyl ketone
O
CHO
(d) trans-4-hydroxycyclohexanecarbaldehyde
OH
Dr. Caroline Clower
Chemistry 2412
Aldehydes and Ketones
3.
Identify any nucleophilic and/or electrophilic atoms in the following molecules.
(a)
Ph3P
CH2
E
N
ON
E
(b)
N
(c)
E
CH3CH2
MgBr
4. Provide structures in the boxes below to complete the following reaction scheme.
O
HO
HC
CH
C
CH
1. NaNH2
H2O, H2SO4
2. Cyclopentanone
HgSO4
HO
3. HCl/H2O
5. Give the major organic product(s) for the following reaction.
O
O
HOCH2CH2CH2OH
HCl
Br
Br
O
C
CH 3
Dr. Caroline Clower
Chemistry 2412
Aldehydes and Ketones
6. Propose mechanisms for the formation of a hemiacetal using each of the following reagents.
O
base
(a)
+
CH3CH2OH
See Wade p. 813; The base will deprotonate the alcohol to make it a better nucleophile.
O
(b)
+
CH3CH2OH
H+
See Wade p. 812. The acid will protonante the carbonyl to make it more electrophilic.
Dr. Caroline Clower
Chemistry 2412
Aldehydes and Ketones
7. Draw the structure of the alcohol and carbonyl compounds formed from acid-catalyzed
hydrolysis of the following acetal.
CH3CH2
O
OCH2CH3
H+
OH O
CH3CH2
8.
CH3CH2OH
+
H
H2O
Provide structures in the empty boxes below to complete the following reaction scheme.
H
H
O
+
NH3
H+
N
H2
H
N
Ni
9. The following alkene can be synthesized using the Wittig reaction. Show both possible routes,
including formation of the phosphonium ylide.
O
1. PPh3
CH3CH2Br
2. BuLi
CH3CH-PPh3
+
O
(CH3)2CHBr
1. PPh3
2. BuLi
(CH3)2C-PPh3
+
H
Dr. Caroline Clower
Chemistry 2412
Aldehydes and Ketones
10. Show reagents and experimental conditions necessary to bring about each of the following conversion.
Et
N
(a)
OH
O
PCC
OH
CH2Cl2
H
1. (CH3)2CHMgBr
2. H3O+
OH
O
N
H2CrO4
H2NCH2CH3
H+
O
(b)
OH
OH
OH
O
PCC
1. CH3MgBr
CH2Cl2
+
2. H3O
OH
H
H+
OH
1. BH3-THF
2. H2O2, NaOH
OH
H2CrO4
O