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Ch 13 Carboxylic Acids.

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Presentation on theme: "Ch 13 Carboxylic Acids."— Presentation transcript:

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


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