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Substituent Effects on Acidity. =>. p K a = 4.46. p K a = 4.19. p K a = 3.47. p K a = 3.41. p K a = 2.16. =>. Salts of Carboxylic Acids. Sodium hydroxide removes a proton to form the salt. Adding a strong acid, like HCl, regenerates the carboxylic acid. Naming Acid Salts.

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substituent effects on acidity
Substituent Effects on Acidity


pKa = 4.46

pKa = 4.19

pKa = 3.47

pKa = 3.41

pKa = 2.16

salts of carboxylic acids


Salts of Carboxylic Acids

Sodium hydroxide removes a proton to form the salt.

Adding a strong acid, like HCl, regenerates the carboxylic acid.

naming acid salts
Naming Acid Salts

Name the cation.

Then name the anion by replacing the -ic acid with -ate.

potassium -chlorovalerate

potassium 3-chloropentanoate =>

properties of acid salts
Properties of Acid Salts

Usually solids with no odor.

Carboxylate salts of Na+, K+, Li+, and NH4+ are soluble in water.

Soap is the soluble sodium salt of a long chain fatty acid.

Salts can be formed by the reaction of an acid with NaHCO3, releasing CO2. =>

some important acids
Some Important Acids

Acetic acid is in vinegar and other foods, used industrially as solvent, catalyst, and reagent for synthesis.

Fatty acids from fats and oils.

Benzoic acid in drugs, preservatives.

Adipic acid used to make nylon 66.

Phthalic acid used to make polyesters. =>

uv spectroscopy
UV Spectroscopy

Saturated carboxylic acids absorb very weakly around 200-215 nm.

If C=C is conjugated with C=O, molar absorptivity = 10,000 at 200 nm.

An additional conjugated double bond increases the absorption wavelength to 250 nm. =>

synthesis review
Synthesis Review

Oxidation of primary alcohols and aldehydes with chromic acid.

Cleavage of an alkene with hot KMnO4 produces a carboxylic acid if there is a hydrogen on the double-bonded carbon.

Alkyl benzene oxidized to benzoic acid by hot KMnO4 or hot chromic acid. =>

grignard synthesis
Grignard Synthesis

Grignard reagent + CO2 yields a carboxylate salt.