Chemistry- Ch 18: Amines and Amides

Naming Amines

“e” to “amine” ex. Methenamine

N- substituted amines

An N-substituted amine is a secondary () or tertiary () amine where one or more hydrogen atoms on the nitrogen are replaced by alkyl or aryl groups (R).

Aromatic Amines

compounds where a nitrogen group is attached directly to an aromatic ring (e.g., aniline).

Substituted Amines

Substituted amines are organic compounds derived from ammonia () where one or more hydrogen atoms are replaced by alkyl or aryl (carbon-based) groups. They are classified as primary, secondary, or tertiary based on the number of organic groups attached to the nitrogen atom.

Skeletal Structures of Amines

When drawing amine skeletal structures, we always show the

hydrogens attached to the amine

• (Just like with alcohols)

Amines and hydrogen bonding

some bond w/ hydrogen

Amine Solubility

Hydrogen bonding increases solubility in water.

Amines

are usually bases and form ammonium salts (or ammonium ions) in water

Neutralization of Amines

Neutralizing amines with acids leads to the formation of only ammonium salts. Ammonium salts do not boil in most cases. Common salts are ammonium

chlorides and ammonium bromides

Ammonium Salts

highly water-soluble, generally white crystalline ionic compounds formed by the reaction of ammonia with acids.

Heterocyclic Amines

mutagenic and carcinogenic compounds containing at least one heterocyclic ring

Alkaloids

They contain at least one nitrogen atom, usually in a heterocyclic ring, derived from amino acids.

Acid Hydrolysis of Amides

involves heating it with an aqueous acid (like HCl) to break the amide bond, yielding a carboxylic acid and an ammonium salt

Base Hydrolysis of Amides

Basic hydrolysis of an amide involves heating it with a strong base (e.g., NaOH) to yield a carboxylate salt and an amine or ammonia.