Chapter 19: Carboxylic Acids

Reactivity of Carboxylic Acids

- carboxylic acids have high boiling points due to the stronger intermolecular forces (H-bonding)

- a strong base (like NaOH) is required to completely deprotonate a carboxylic acid

- carboxylic acids are more acidic when:

1) they have more EWGs

2) the carbonyl is close to the EWG (induction)

Preparation of Carboxylic Acids (Review)

1) Oxidative Cleavage of Alkynes

Alkyne → Carboxylic Acid

Reagents: 1) O3 / 2) H2O

2) Oxidation of 1° Alcohols

1° Alcohol → Carboxylic Acid

Reagents: Na2Cr2O7, H2SO4, H2O

3) Oxidation of Alkylbenzenes

Alkyl on Benzene → Carboxylic Acid

Reagents: Na2Cr2O7, H2SO4, H2O

4) Preparation of Carboxylic Acids via Baeyer-Villiger Oxidation

4) Baeyer-Villiger Oxidation

Aldehyde → Carboxylic Acid

Reagents: m-CPBA (peroxy acid)

5) Preparation of Carboxylic Acids via Carboxylation of Grignard Reagents

5) Carboxylation of Grignard Reagents

Grignard Reagent (R-MgBr) → Carboxylic Acid

Reagents: 1) CO2 / 2) H30+

Reduction of Carboxylic Acids

Starting Material: Carboxylic Acid

Carboxylic Acid → Reduced to Alcohol

Reagents: 1) LAH / 2) H30+