Chapter 20- Carboxylic acids and Nitriles

Oxidation of an Alkyl Benzne

Forms a Carboxylic Acid

Reagents: KMNO4/H2)

Primary and secondary alkyl groups can be oxidized.

Oxidation of Primary alcohol or aldehyde

Forms a carboxylic Acid

1) Uses KMNO4 or strong oxidizing agent

Carboxylation of Gringard reagents

Results in Carboxylic Acid

Reactands: Gringard + CO2

Carboxylation facilitated by CO2 and H3O+

Hydrolysis of Nitriles

Results in a carboxylic acid

1) Alkyl Halide + NaCN

2) NaOH/ H3O+

General Reactions of Carboxylic acids

Deprotonation

Alpha Substituition

Reduction

Nucleophilic Acyl Substituition

Henderson Hasselbach Reaction

pH=pKa​+log([A-]/[HA−]​)

• pKa​ is the acid dissociation constant,

• [A−][A−] is the concentration of the conjugate base,

• [HA][HA] is the concentration of the acid.

Carboxylic Acid + Gringard reagent

NO REACTION

Acid protons are too acidic, and can protonate gringard, nuetralizinf it before it can react with carboxylate group

Both COOH and CN are

Electrophiles and go through Nucleophilic addition rxns

Prep of simple nitirle

SN2 reaction of CN- with a primary or secondary Alkyl Halide

Preparation of complex nitriles

Dehydration of primary amide with SOCl2

results in R-C:::N

Nitrile + H2O

Forms an amide through Imine intermediate, which tautomerizes to form the amide form

Amide + H2O

Forms a carboxylic Acid

Nitrile + gringard reagent in water

Forms a KETONE + NH3

Nitirle plus strong oxidizing agent (LIalH4)/Ether

Forms an Amine (NH2)

Carboxylic acid + LiALH4

Reduction reaction- results in an Alchol