Ch 13 Carboxylic Acids, Esters,
Amines and Amides
SWBAT:
Name/Draw compounds with functional groups
Describe/Explain properties of functional groups
Complete/Show reactions of functional groups
Chapter 13.1
Carboxylic Acids
Carboxylic Acids
• Functional Group: Carboxyl Group
– Carbonyl and Hydroxyl at the same carbon
• Condensed writing: COOH
• Carboxyl Carbon is C #1
• Alkyl prefix….end in -oic acid
methanoic acid
methylpropanoic acid
3-methylpentanoic
acid
Benzoic Acid
•
•
•
•
Carboxyl on a benzene
Carboxyl is attached to C #1
List all substituents by alpha
Number either cw or ccw in
order to get lowest numbers!
4-bromo-2-methylbenzoic acid
Naming Practice
• Parent alkane has to include carboxylic acid
Drawing Practice
Draw:
2-methyl-3-phenyl-pentanoic acid
4-iodo-2-isopropyl-benzoic acid
Common Names
Fatty Acids
• Very long carboxylic acids
• Which one has a higher boiling pt? Why?
• Which one is a solid (fat) which a liquid (oil) at RT
Alpha Hydroxy Acids (AHA)
• Hydroxyl groups on the α Carbon: Carbon # 2
• Natural occurring acids in sour milk and fruits
• Part of many skin care products to exfoliate and
smooth skin
Homework
Chapter 13
Page 430 13.6 and 13.8
Chapter 13.2
Properties of Carboxylic Acids
Acid Behavior
• Acids are Hydrogen (H+) Donors
• Carboxylic Acids dissociate in water and lower
the pH
aq
COOH + H2O → COO- + H3O+
carboxylate ion & hydronium ion
Boiling Point
• Carboxylic Acids have
the highest boiling
point of organic
molecules
• More partial charges
(4) than alcohols (3)
Solubility
• Carboxylic Acids dissolve very well in water
• Form H-bonds with water molecules
• But the longer the C-chain, the less soluble!
Solubility
Chapter 13.2 continued
Reactions of carboxylic acids
Dissociation Rx
• When carboxylic acids dissociate they form a
carboxylate ion
Example:
HCOOH → HCOO- + H+
Methanoic Acid
Methanoate Ion
Neutralization Rx
• Carboxylate anions can react with metal
cations to form carboxylic acid salts:
COOH + NaOH → COO-Na+ + H2O
Sodium methanoate
Name the following:
Potassium ethanoate
or Potassium acetate
Pentanoate Ion
Homework
Chapter 13
Page 434 13.10 – 13.16