ET III Ch. 18 Amines and Amides

What are amines?

Organic derivatives of ammonia in which one or more of the three hydrogens of NH3 have been replaced by alkyl (R) or aromatic groups

What do amines have in common with alcohols?

They may be designated as primary, secondary, or tertiary according to the position of attachment of the nitrogen

What is the general formula for an amine?

R-NH2

Match a photo of ammonia

Match a photo of a primary amine

Match a photo of a secondary amine

Match a photo of a tertiary amine

Amines are characterized by a strong ____-like odor

Fish

Amines are produced as he products of what?

proteins and other nitrogenous animal and plant substances

What are amines commonly referred to as?

Intermediate products of decomposition

• Also commonly called ptomaines

Where does ptomaines get its name from?

From the Greek word ptoma, meaning “corpse”

Give two examples of ptomaines

• Putrescine

• Cadaverine

What are putrescine and cadaverine?

Diamines

Why are ammonia and its derivative substances (the amines) basic?

Because of the presence of an unshared pair of electrons

Because of the unshared pair of electrons on the nitrogen, ammonia, along with its constituent amides, act like a ________________ Base.

Lewis

It is because of this _________ that bodies with an excessive build-up of amines or other nitrogenous waste products will neutralize formaldehyde

alkalinity

How are amides produced?

Produced when amines react with carboxylic acids.

what type of reaction is created when amides are produced?

A neutralization reaction

What is produced in a neutralization reaction?

A salt and a water

How are amides named?

by replacing the –ic suffix of the reacting acid with -amide

What is urea?

Waste product of human protein metabolism secreted into the blood by the liver and selectively absorbed and excreted into the urine by the kidneys

What is the simplest aeromatic amine?

aniline

• a commonly used dye obtained from the indigo plant.

What does heterocyclic mean when referring to heterocyclic amines?

that two different elements are in the ring

• both 5 and 6 membered heterocyclic amines are important in biological systems

what are 5 membered heterocyclic amines that contain one nitrogen in the ring called?

Pyrrole

What are 5 membered rings with one nitrogen in the ring (pyrrole) the basis for?

for a number of important compounds including a Porphyin ring, which is composed of 4 pyrrole rings linked by carbon atoms.

• What is indole?

A heterocyclic amine that contains a pyrrole bonded to a benzene ring.

• Indole smells intensely fecal and musty at high concentrations, like mothballs or decay

What is skatole?

A derivative of Indole that contains a methyl group attached to the pyrrole.

• (smells like fecal matter, baby poop, old diaper)

What are 6 membered heterocyclic amines called?

Pyridine

What is a pyridine?

A 6 membered ring with one nitrogen in the ring

What are 6 membered rings with one nitrogen in the ring (pyridine) the basis for?

for many biological substance Including vitamins hormones and antibacterial agents.

What do you get when there are two nitrogen’s in a 6-membered heterocyclic amine?

Pyrimidine

What is pyrimidine?

one of the two types of nitrogenous bases that form the molecular basis for life, nucleic acids, DNA & RNA

What pyrimidines are found in DNA & RNA?

Thymine, cytosine, and uracil

What is the second type of nitrogenous base found in nucleic acids?

Purine

In order to produce the second type of nitrogenous base found in nucleic acids, What needs to be combined?

the diamino pyrimidine with its analogous 5-membered ring, imidazole. The result is a Purine.

What two nitrogenous bases contain a purine nucleus that are important to DNA & RNA?

Adenine & Guanine

Caffeine is also a ___________ derivative

Purine

How is a quaternary ammonium ion formed?

When all hydrogens of an amine have been replaced with a hydrogen ion, an alkyl group, or an aromatic group

Compounds derived from quaternary ammonium ions are called

quaternary ammonium salts

What properties do some quaternary ammonium salts have?

• Detergent

• Disinfectant

What renders any alkaline substance useless?

Soap

How does soap render quats useless?

Reaction between the cation of a quat and the negative ion of soap molecules produces an insoluble salt, thus removing the quat from the solution