1. Ch 13 Carboxylic Acids

2. Carboxylic Acids
Functional Group: Carboxyl Group (Carbonyl and Hydroxyl at the same carbon has a new name!)
Condensed writing: COOH
Carboxyl Carbon is C#1
Alkane name, drop e replace with -oic acid
2 word name: Methanoic acid

3. Benzoic Acid Carboxyl on a benzene Carboxyl is attached to C#1
List all substituent alpha and
Number either cw or ccw so you
get lowest numbers!
4-bromo-2-methylbenzoic acid

4. Naming Practice
Parent alkane has to include carboxylic acid, which is THE highest oxidized functional group

5. Drawing Practice Draw: 2-methyl-3-phenyl pentanoic acid
4- Iodo-2-isopropyl benzoic acid

6. Common Names of Carboxylic Acids

7. Fatty Acids
Very long carboxylic acids

8. AHA: Alpha Hydroxy Acids
Hydroxyl groups on the α Carbon: Carbon # 2
Super polarity on this end!!!
Natural occurring acids in sour milk and fruits
Part of many skin care products to exfoliate and smooth skin

9. Properties of Carboxylic Acids

10. Acid Behavior Acids are H+ Donors
Carboxylic Acids dissociate in water and lower the pH
COOH + H2O → COO- + H3O+
carboxylate ion and
hydronium ion

11. Intermolecular Forces
Molecule class
Van de Waals
Dipoles
H-Bonds
alkanes
Ethers, aldehydes, ketones
alcohols
Carboxylic acids

12. Intermolecular Forces
Molecule class
Van de Waals
Dipoles
H-Bonds
alkanes
yes no
Ethers, aldehydes, ketones
alcohols
yes (1)
Carboxylic acids
Yes (2)
yes (2)

13. H-bonds between Carboxyls

14. Boiling Point Carboxylic Acids have the highest boiling point
of organic molecules
More partial charges (4)
than alcohols (3)

15. Solubility Carboxylic Acids dissolve very well in water
form H-bonds with water molecules
But the longer the C-chain, the less soluble!

16. Solubility

17. Rx of Carboxylic Acids

18. Dissociation Rx Example: HCOOH → HCOO- + H+
when carboxylic acids dissociate they form a carboxylate ion
Example:
HCOOH → HCOO- + H+
Methanoic Acid Methanoate Ion
Naming of Ion:
Acid name: Methano-ic replace by –ate ion
Condensed structure: CH3-CH2-COO-

19. Neutralization Rx Acid + Base → Salt + water
Carboxylate anions can react with metal cations to form carboxylic acid salts:
CH3COOH + NaOH → CH3COO-Na+ + H2O
Sodium ethanoate
Draw in stick…

20. Esterification Rx Carboxylic Acid + Alcohol → Ester + H2O H2O
Ethanoic Acid Methanol Methyl ethanoate

21. Name of Ion and Salt
Name: a) b) Potassium ethanoate Pentanoate Ion Or Potassium acetate

22. CA in Nature
Flavor enhancer: Sodium glutamate

23. Benzoic Acid
Common Preservative

24. Aspirin
Common analgesic