Amines and Amides
Ques. 1. Identify the following amines as primary, secondary, tertiary, or ammonium ion.
Also name each one.
H
3
C
H
N
C
H
2
H
2
C
CH
3
H
2
C
H
3
C
N
CH
2
H
2
N
H
2
C
C
H
2
H
2
C
CH
3
H
3
C
H
2
C
NH
3
+
Cl
-
H
3
C H
2
C C H
3
Ques. 2. a. Draw three molecules of ethylamine engaged in hydrogen bonding. b. Explain why trimethylamine can not form hydrogen bonds.
Ques. 4. Explain the difference and rank them in order of lowest to highest boiling points of ethyl methylamine, 1-propanol, trimethyl amine, and propylamine,. Include points about relative polarity and hydrogen bonding.
Ques. 5. Write the ionization reactions for dimethylamine trimethylamine ethylamine.
Ques. 6. Write the following neutralization reactions: a. ethylamine + HCl ---> b. ethyl propylamine + HBr ---> c.
H
N
+ HCl
H
3
C CH
3
Ques. 7. Why are many drugs listed in the ingredients as the hydrochloride - example
Sudafed is listed as ephedrine hydrochloride; Novocain, local anesthetic is the hydrochloride salt of procaine. Think about polarity of amines , salts, and solubility in water.
Ques. 8: Name the amides in the structures below:

Ques 9. Write the products of reactions for the synthesis of amides. Give the names of both the reactants and the products.
O a.
H
3
C
C
H
2
C
OH
+
H
2
N
H
2
C
CH
3
O b.
H
3
C
H
N
CH
3
+
H
3
C C
OH
H
3
C
H
2
C
NH
2
+
H
3
C
O
H
2
C
C
H
2
C
OH d.
H
2
N
H
2
C
C
H
2
H
2
C
CH
3
+
H
3
C
C
O
OH
O
NH
2
+
H
3
C C
H
3
C
C
H
2
OH e. d.
H
3
C CH
2
O
O NH
2
+
H
3
C C
OH acetaminophen
Tylenol
Ques. 10. Which is more polar and can have more possibilities for hydrogen bonding?
Ethylamine or ethanamide. Explain

Ques. 11. Complete the acid hydrolysis of the following amides. Give the names of the reactants and the products. Note: First make the amine and the acid, then if an acid is used as a catalyst, then the amine must form a salt with the excess acid. a.
H
3
C
H
2
C
O
NH
C CH
2
CH
3
+ HOH + HCl
CH
3 b.
H
2
C
N
O
C
C
H
2
H
2
C
+ HOH + HCl
CH
3
CH
2 c.
H
3
C
H
3
C
HN
O
C
H
2
C CH
3
+ HOH
HCl second step d.
O
H
3
C
H
2
C
N
H
C
C
H
2
H
2
C
CH
3
+ HOH
HCl second step