1. 16.1 Carboxylic Acids
A carboxylic acid contains a carboxyl group, which consists of a hydroxyl group
to the carbon in a carbonyl group.

2. IUPAC Names for Carboxylic Acids
In the IUPAC names of carboxylic acids,
the e in the alkane name is replaced with oic acid.

3. 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).

4. 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.

5. Chemistry Link to Health: Alpha Hydroxy Acids
Alpha hydroxy acids (A H A s)
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 A H A s to remove acne scars and in skin peels to reduce irregular pigmentation and age spots.

6. Chemistry Link to Health: Alpha Hydroxy Acids
Several different alpha hydroxy acids may be found in skin care products singly or in combination.
Alpha Hydroxy Acid (Source)
Condensed Structural Formula
Glycolic acid
(sugar cane)
carboxyl group bonded to C H 2 bonded to an O H group.
Lactic acid
(sour milk)
carboxyl group bonded to C H bonded to a C H 3 group and an O H group.
Tartaric acid
(grapes)
2 carboxyl groups, one on each end, bonded to 2 carbons, each bonded to an O H group
Malic acid
(Apples)
2 carboxyl groups, one on each end, bonded to 2 carbons, one bonded to an O H group
Citric acid
(citrus fruits)
central carbon bonded to an O H group, a carboxyl group, and 2 C H 2 groups each bonded to a carboxyl group.

7. 16.2 Properties of Carboxylic Acids
Carboxylate salts are often used as preservatives and flavor enhancers in soups and seasonings. Sodium propionate, a preservative, is added to cheeses, bread, and other bakery items to inhibit the spoilage of the food by microorganisms.

8. Polarity of Carboxylic Acids
Carboxylic acids are strongly polar because they have two polar groups:
a hydroxyl group
a carbonyl group (C = O).

9. Solubility in Water Carboxylic acids
form hydrogen bonds with many water molecules.
with one to five carbon atoms are very soluble in water.
are less soluble as the number of carbons increases.
Acetic acid forms hydrogen bonds with water molecules.

10. Acidity of Carboxylic Acids
are weak acids.
dissociate in water to produce carboxylate ions and hydronium ions.
can lose a proton because two oxygen atoms in a carboxylate ion stabilize negative charge.

11. Neutralization of Carboxylic Acids
Carboxylate salts are a product of the neutralization of a carboxylic acid with a strong base such as N a O H or K O H. The carboxylate ion is named by replacing the ic acid ending of the acid name with ate.

12. Carboxylic Acids, Preservatives
Sodium propionate, a preservative, is added to bread, cheeses, and bakery items to inhibit the spoilage of the food by microorganisms.
Sodium benzoate is added to juices, margarine, relishes, salads, and jams to inhibit the growth of mold and bacteria.

13. Carboxylic Acids, Preservatives
Monosodium glutamate (MSG) is added to meats, fish, vegetables, and bakery items to enhance flavor, although it may cause headaches in some people.

14. Chemistry Link to Health: Carboxylic Acids in Metabolism
At the pH of the aqueous environment in the cells,
the carboxylic acids are dissociated.
it is actually the carboxylate ions that take part in the reactions of the citric acid cycle.
For example, in water, succinic acid is in equilibrium with its carboxylate ion, succinate.

15. Chemistry Link to Health: Carboxylic Acids in Metabolism
Carboxylates are part of the metabolic processes within our cells. For example,
during glycolysis, a molecule of glucose is broken down into two molecules of pyruvate, the carboxylate salt of pyruvic acid.
during strenuous exercise when oxygen levels are low (anaerobic), pyruvate is reduced to give lactic acid or the lactate ion.

16. Chemistry Link to Health: Carboxylic Acids in Metabolism
In the citric acid cycle (Krebs cycle),
di- and tricarboxylates are oxidized and decarboxylated (loss of C O2) to produce energy for cells.
citrate, with six carbons, is oxidized to a five-carbon

17. Chemistry Link to Health: Carboxylic Acids in Metabolism
The citric acid cycle continues as
loses C O2 to give a four-carbon succinate.
a series of reactions then converts succinate to oxaloacetate.

18. 16.3 Esters By the 1800s, chemists had discovered that
salicin from willow tree bark and leaves was responsible for pain relief.
the body converts salicin to salicylic acid, which irritates the stomach lining.
Bayer discovered that an ester form of the compound, acetylsalicylic acid, is less irritating but still effective.

19. Esters
Esters are
synthesized from the reaction of a carboxylic acid and alcohol.
found in fats and oils.
responsible for the aroma and flavor of bananas, oranges, and strawberries.

20. Chemistry Link to Health: Salicylic Acid from a Willow Tree
In 1899, the Bayer chemical company
produced an ester of salicylic acid and acetic acid less irritating to the stomach than salicylic acid.
called the ester acetylsalicylic acid (aspirin).
Many people take a daily low-dose aspirin, which has been found to lower the risk of heart attack and stroke.

21. Chemistry Link to Health: Salicylic Acid from a Willow Tree
Oil of wintergreen, or methyl salicylate, has a pungent, minty odor and flavor and
is used in skin ointments.
can pass through the skin.
acts as a counter-irritant, producing heat to soothe sore muscles.

22. Chemistry Link to Environment: Plastics
Dacron has many uses; it
forms a permanent-press fabric that resists wrinkles.
is used to make artificial blood vessels and valves that are biologically inert and does not clot blood.
Is made into a film called Mylar and a plastic known as P E T E (polyethyleneterephthalate) used for plastic drink bottles.

23. Esters in Fruits
Many of the fragrances of perfumes and flowers and the flavors of fruits are due to esters.
Small esters are volatile, so we can smell them, and they are soluble in water, so we can taste them.
The odor of grapes is due to ethyl heptanoate.

24. Esters in Fruits and Flavoring
Table 16.3 Some Esters in Fruits and Flavorings