Chemistry 130
Worksheet 6 Notes
Oregon State University
Dr. Richard Nafshun
1. Draw an amine that contains six carbon atoms. Identify the lone pair of electrons in the
molecule. Name it.
1-hexylamine
2. Draw the structures that correspond to the following names:
a) Butylamine
NH2
b) Dipropylamine
NH
c) N-Ethylhexylamine
N
H
3. Below is the structure of cocaine. Identify the functional groups in the molecule.
Tertiary amine
esters
4. Most illicit cocaine is cocaine hydrochloride, a product of the reaction of cocaine with
HCl. Show the product of this reaction. Which is more soluble and why?
+
+ Cl-
5. Predict the products of the following reactions:
a)
+ HBr
NH3+
NH2
b) CH3CH2NHCH3
+
H3O+
→
CH3CH2NH2+CH3
+
H2O
+ Br -
c) CH3CH2CH2NH3+
+
OH-
→ CH CH CH NH
3
2
2
2
+
H2O
6. 1-Propylamine, 1-propanol, acetic acid and butane have about the same molecular
weight. Which has (be sure to explain!):
a) The highest boiling point
Acetic acid – it is most polar of all and undergoes more extensive H-bonding.
b) Lowest boiling point
Butane. Nonpolar and no H-bonding
c) Highest solubility in water
Acetic acid. Strongest H-bonding on COOH group.
d) Lowest solubility in water.
Butane. Nonpolar and no H-bonding
7. Lemon juice or vinegar is frequently suggested for removing odor associated with
cleaning fish. What kinds of compounds are responsible for the fishy odor and what do
lemon juice (contains citric acid) or vinegar (contains acetic acid) do to remove the odor?
Acids from vinegar or lemon juice react to form non-volatile (and water soluble) amine salts.
This is another reason why people put lemon on fish to enhance its flavor.
8. Identify the carboxylic acid(s) and amine(s) this polyamide was synthesized from.
HN-CH2- CH2- CH2- CH2- CH2- CH2-NH and HOOC- CH2- CH2- CH2- CH2-COOH