Week 4: Acids and Esters
Lecture # 9, 10, 11
Concepts: Acids, ionization, boiling point.polarity, solubility, salts,
neutralization
Reaction Summary: Write the word equations.
Self Ionization of Acids in Water Neutralization of Acid with Base Synthesis of Acids Ester Synthesis Ester Hydrolysis acidic and basic Ques. 1. Which compound in each pair will have the highest boiling point and
thus be the most polar?
a.
b.
c.
d.
e.
heptane or nonane
1-propanol or methyl ethyl ether
1-propanol or propylamine
1-propanol or propanoic acid
1 butanol or methyl propanoate
Ques. 2. Rank the following compounds in order of increasing polarity. 1 =
most non-polar.
CH3OH, CH3CH3, CH3NH2, CH3-OCH3, CH3COOH, CH3OOCCH3
Ques. 3. A. Rank the following compounds in order of increasing solubility in
water.
1 = most insoluble.
pentanoic acid, pentane, 1-pentanol, ethyl propyl ether
B. Rank the following compounds in order of increasing solubility in water.
1 = most insoluble.
Ethanoic acid, hexanoic acid, butanoic acid, methanoic acid
Ques. 4: Show how acetic acid can hydrogen bond to make a dimer. Also show
how acetic acid can hydrogen bond with water, but that methyl ethanoate is
unable to hydrogen bond to each other.
Ques 5. Rank the following compounds in order of increasing solubility in
hexane.
1 = most insoluble.
butane, butanol, butanoic acid, diethyl ether, methyl propanoate
Ques. 6. Write the reaction for the synthesis of carboxylic acids. Name the
reactants and the products.
H2
C
A.
H
C
H3C
+ Oxidizing Agent
C
H2
O
CH3
B.
H2C
H3C
O
CH
H2C
+ Oxidizing Agent
CH
Ques. 7. Write the reaction for the self ionization of carboxylic acids in water.
Name the reactants and the products.
O
H 3C
A.
+ H2O
C
C
H2
OH
CH3
O
+ H 2O
B.
CH
H3C
C
C
H2
OH
Neutralization Reaction or Salt Formation
Reaction Name
Word Equation
Example
20. Acid Salt reaction
Acid + MOH M= Na, K, Li,
 metal ion acid salt
Ethanoic aicd + NaOH
Ques. 8. Write the reaction for the neutralization of carboxylic acids in with base
to form salts. Name the reactants and the products.
O
+ KOH
A.
C
OH
H3C
H3C
B.
H3C
O
CH
+ KOH
C
OH
12. Ester Synthesis
Alcohol + acid
 ester + water
Methanol + ethanoic acid
Ques. 9. Write the reaction for the synthesis of ethers and esters. Name the
reactants and the products.
H2
C
A.
H3C
OH
H3C
H2
C
HO
C
H2
CH3
O
H2
C
B.
+
OH
+
C
HO
CH3
C
H2
CH3
O
C.
H3C
C
+
HO
C
OH
H2
Ques. 10: Write the names of the following:
CH
CH3
Ques. 11: Synthesis of Esters Write names of reactants and products:
a.
O
H2
C
H3C
OH
H2
C
+
H3C
C
H2
b.
+
C
OH
H2
C
O
H3C
C
HO
H2
C
C
H2
CH3
butanol
OH
c.
O
H2
C
H3C
C
H2
+
C
C
H2
OH
H3C
OH
d.
O
H3C
OH
+
H3C
C
C
H2
OH
Hydrolysis Reactions - add water to split a molecule (reverse of combination
reactions)
Reaction Name
Word Equation
Example
17. Ester Hydrolysis
Ester + HOH
Methyl ethanoate + HOH
 alcohol + acid
Ques. 12: Hydrolysis of Esters: Name the reactants and products
a.
O
H2
C
H3C
H2
C
C
H2
C
O
CH3
H2
C
CH3
+
HOH
+
HOH
b.
O
H3C
C
O
C
H2
C
H2
Basic Hydrolysis (NaOH)
Second step: neutralize acid with NaOH
c.
O
H3C
C
O
C
H2
+
CH3
HOH
Basic Hydrolysis (NaOH)
Second step: neutralize acid with NaOH
Ques. 13. Write the reaction for the hydrolysis of esters. Name the reactants and
the products.
O
Acid Hydrolysis
H2
C
A.
H3C
CH3
C
O
CH2
C
H2
O
B.
H3C
C
O
CH3
+ NaOH (Basic Hydrolysis)
Ques. 14. Neutralize the following fatty acid with NaOH. Then explain the
specifics of how the soap molecule works to clean dirt. How does it act as a
“bridge” between oil and water? Use the concepts of micelle, polar and non
O
HO
polar.
Ques. 15. Write the reaction for the synthesis of ethers and esters. Name the
reactants and the products.
OH
C
O
C
+ H3C
OH
could get two
products
C
OH
OH
C
O
O
+
C
C
C
OH
OH
aspirin
H 3C
b. Which structure above is salicylic acid, aspirin and which is oil of
winter green?
Ques. 16. Explain how a polyester is made. You do not need to write the
reaction, but do need to explain how the reaction is similar but different from the
other ester synthesis we have been doing.