Chem 30B Homework 4
Name __________________
1. Name the following structures.
O
OH
CH3 CH
CH2 C
CH3
O
Name
Name
OH
O
CH3 CH2 CH
CH
O
Name
Name
CH3
O
H
C
H
CH3 CH
CH2 C
O
Name
2. Draw the structures of the following molecules.
a. 3-ethyl-3-isopropyl-2-methyl hexanal
b. 2-ethyl cyclobutanone
c.
3-hydroxy cyclpentanone
d. 2,3,4 tribromo hexanal
Name
H
3. Classify the following as hemiacetal, hemiketal, acetal, ketal, or none of the above. Circle
appropriate answer.
HO
CH3
Hemiacetal
Hemiketal
Acetal
Ketal
CH3
O
None of the above
OCH2CH2CH3
H
C
Hemiacetal
Hemiketal
Acetal
Ketal
OCH2CH3
H
None of the above
CH2CH2CH3
H
C
Hemiacetal
Hemiketal
Acetal
Ketal
OCH2CH3
H
HO
O
None of the above
H
Hemiacetal
Hemiketal
Acetal
Ketal
CH3
None of the above
4. Rank the following molecules from lowest to highest solubility. Place the letter
representing the molecule in the appropriate space.
Lowest (solubility)
_____
_____
Highest (solubility)
CH3
O
CH3 C
_____
CH3
H
C
CH3
OH
CH3
OH
A
CH
CH3
B
C
5. Rank the following molecules from lowest to highest boiling point. Place the letter
representing the molecule in the appropriate space.
Lowest (boiling point)
A
_____
_____
OH
O
CH3 C
_____
CH3
CH3 CH
Highest (boiling point)
O
CH2 CH3
B
CH3 C
CH2 CH3
C
6. Draw a picture of two water molecules forming hydrogen bonds to ethanal.
7. Complete the following reactions by giving the product that will form.
O
[O]
CH3 CH2 CH
O
CH3 CH2 CH
+ CH3OH
O
+ CH3OH
CH3 CH2 C
(H+)
+ CH3OH
H3CO
+ CH3OH
+
(H )
O
H
CH3
8. Circle the carbonyl group in the following molecule. Indicate the partial charges that
result in the portion of the molecule.
O
CH3 C
CH2 CH3
9. Determine the product in the following reaction.
O
OH
CH3 C
CH2 CH2 CH2 CH
CH3