Ch 13 Carboxylic Acids, Esters, Amines and Amides

SWBAT:Name/Draw compounds with functional groupsDescribe/Explain properties of functional groupsComplete/Show reactions of functional groups

Chapter 13.1Carboxylic 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

HomeworkChapter 13

Page 430 13.6 and 13.8

Chapter 13.2Properties 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 continuedReactions 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:

Pentanoate IonPotassium ethanoate or Potassium acetate

HomeworkChapter 13

Page 434 13.10 – 13.16