1. Chapter 16 Carboxylic Acids
Lecture Presentation
Chapter 16 Carboxylic Acids
and Esters
Karen C. Timberlake

2. Chapter 16 Carboxylic Acids and Esters
Surgical technicians prepare the operating room and the patients for surgery by
creating a sterile environment in the surgical room.
washing, shaving, and disinfecting incision sites.
During the surgery, a surgical technician provides the sterile instruments and supplies to the surgeons and surgical assistants.

3. Chapter 16 Readiness Core Chemistry Skills
Writing Equations for Reactions of Acids and Bases (11.7)
Naming and Drawing Alkanes (12.2)

4. 16.1 Carboxylic Acids
A carboxylic acid contains a carboxyl group, which consists of a hydroxyl group —OH attached to the carbon in a carbonyl group.
Learning Goal Write the IUPAC and common names for carboxylic acids, and draw their condensed and line-angle structural formulas.

5. IUPAC Names for Carboxylic Acids
In the IUPAC names of carboxylic acids,
the e in the alkane name is replaced with oic acid.
CH4
Methane Methanoic acid
CH3—CH3
Ethane Ethanoic acid

6. IUPAC Names for Carboxylic Acids
Substituents are numbered from the carboxyl, which is carbon 1.

7. IUPAC Names for Carboxylic Acids
As before, for benzoic acid, the placement of substituents is shown using the prefixes ortho, meta, and para.

8. IUPAC Names for Carboxylic Acids
Many carboxylic acids are still named by their common names, which use prefixes: form, acet, propion, butyr.
When using the common names, the Greek letters alpha (α), beta (β), and gamma (γ) are assigned to the carbons adjacent to the carboxyl carbon.

9. Common Carboxylic Acids
A red ant sting contains methanoic acid (formic acid) that irritates the skin.
The sour taste of vinegar is due to ethanoic acid (acetic acid).

10. Guide to Naming Carboxylic Acids

11. Naming Carboxylic Acids
Give the IUPAC and common name for the following carboxylic acid:
ANALYZE Given Need
THE carboxylic acid IUPAC and
PROBLEM common name

12. Naming Carboxylic Acids
Give the IUPAC and common name for the following carboxylic acid: STEP 1 Identify the longest carbon chain and replace the e in the alkane name with oic acid. The IUPAC name for a carboxylic acid with three carbons is propanoic acid. The common name is propionic acid.

13. Naming Carboxylic Acids
Give the IUPAC and common name for the following carboxylic acid:
STEP 2 Name and number any substituents by counting the carboxyl group as carbon 1.
IUPAC name 2-methylpropanoic acid
Common name 2-methylpropionic acid

14. Study Check
Give the IUPAC name of each compound. A. B.

15. Solution
Give the IUPAC name of each compound. A. B.
3-hydroxypentanoic acid
3-bromobenzoic acid

16. Study Check
Draw the line-angle structure for 4-chlorohexanoic acid.

17. Solution
Draw the line-angle structure for 4-chlorohexanoic acid.

18. Preparation of Carboxylic Acids
can be prepared from primary alcohols or aldehydes.
can be produced from the oxidation of primary alcohols to aldehydes and then to carboxylic acids.
Ethanol in wine is oxidized by oxygen in the air, converting the primary alcohol to acetaldehyde and then to acetic acid, the carboxylic acid in vinegar.

19. Chemistry Link to Health: Alpha Hydroxy Acids
Alpha hydroxy acids (AHAs)
are found in fruits, milk, and sugar cane.
are naturally occurring carboxylic acids with a hydroxyl group on the carbon atom that is adjacent to the carboxyl group.
Dermatologists have been using products with high concentrations (20–70%) of AHAs to remove acne scars and in skin peels to reduce irregular pigmentation and age spots.

20. Chemistry Link to Health: Alpha Hydroxy Acids
Several different alpha hydroxy acids may be found in skin care products singly or in combination.