AMINED AND AMIDES

Nitrogen

is a member of Group VA of the periodic table.

Nitrogen

It has five valence electrons and will form three covalent bonds to complete its octet of electrons

amine

is an organic derivative of ammonia (NH3)in which one or more alkyl, cycloalkyl, or aryl groups are attached to the nitrogen atom.

primary amine

is an amine in which the nitrogen atom is bonded to one hydrocarbon group and two hydrogen atoms.

primary amine

The generalized formula for a __ is RNH2

secondary amine

is an amine in which the nitrogen atom is bonded to two hydrocarbon groups and one hydrogen atom.

secondary amine

The generalized formula for a __ is R2NH

tertiary amine

is an amine in which the nitrogen atom is bonded to three hydrocarbon groups and no hydrogen atoms.

tertiary amine

The generalized formula for a __ is R3N.

Tert-butyl alcohol

is a tertiary alcohol, whereas tert-butylamine is a primary amine.

Secondary and tertiary amines

possess substituted amino groups.

substituent

In amines where additional functional groups are present, the amine group is treated as a __

amino group

—NH2 group is called an __

aniline

simplest aromatic amine, a benzene ring bearing an amino group, is called __

isomers

Different carbon atom arrangements produce __

methylamines (mono-, di-, and tri-) and ethylamine

are gases at room temperature and have ammonia-like odors

amines

Most other __ are liquids, and many have odors resembling that of raw fish.

diamines

have strong, disagreeable odors.

amines released by the bacterial decomposition of protein

The foul odor arising from dead fish and decaying flesh is due to __

diamines putrescine and cadaverine

Two of these “odoriferous” compounds are the __

simpler amines

are irritating to the skin, eyes, and mucous membranes and are toxic by ingestion.

Aromatic amines

are generally toxic. Many are readily absorbed through the skin and affect both the blood and the nervous system.

Neurotransmitter

is a chemical substance that is released at the end of a nerve, travels across the synaptic gap between the nerve and another nerve, and then bonds to a receptor site on the other nerve, triggering a nerve impulse.

Norepinephrine

a compound secreted by the adrenal glands into the blood, helps maintain muscle tone in the blood vessels.

Dopamine

- is found in the brain. A deficiency of this neurotransmitter results in Parkinson’s disease, a degenerative neurological disease.

Serotonin

also a brain chemical, is involved in sleep, sensory perception, and the regulation of body temperature

Epinephrine

also known as adrenaline, has some neurotransmitter functions but is more important as a central nervous system stimulant.

Histamine

is responsible for the unpleasant effects felt by individuals susceptible to hay fever and various pollen allergies.

Alkaloids

is a nitrogen-containing organic compound extracted from plant material.

Morphine

is one of the most effective painkillers known, its painkilling properties are about a hundred times greater than those of aspirin.

Codeine

is less potent than morphine, having a painkilling effect about one-sixth that of morphine.

Heroin

is a semi-synthetic compound, the diacetyl ester of morphine; it is produced from morphine.

Alkylation

in the presence of base.

quaternary ammonium salt

is an ammonium salt in which all four groups attached to the nitrogen atom of the ammonium ion are hydrocarbon groups.

AMIDES

is a carboxylic acid derivative in which the carboxyl —OH group has been replaced with an amino or a substituted amino group.

Primary amide

is an amide in which two hydrogen atoms are bonded to the amide nitrogen atom.

Secondary amide

is an amide in which an alkyl (or aryl) group and a hydrogen atom are bonded to the amide nitrogen atom.

Tertiary amide

is an amide in which two alkyl (or aryl) groups and no hydrogen atoms are bonded to the amide nitrogen atom.

simplest amide

has a hydrogen atom attached to an unsubstituted amide functional group.

simplest aromatic amide

involves a benzene ring to which an unsubstituted amide functional group is attached.

lactams

Cyclic amides are called

lactams

a term that parallels the use of the term lactones for cyclic esters.

y-lactam

A lactam with a five-membered ring is a __

b-lactam ring

The members of the penicillin family of antibiotics have structures that contain a __

Urea

a water-soluble white solid produced in the human body from carbon dioxide and ammonia through a complex series of metabolic reactions.

uremia

With malfunctioning kidneys, urea concentrations in the body can build to toxic levels—a condition called __

Melatonin

is a hormone that is synthesized by the pineal gland and that regulates the sleep–wake cycle in humans.

Acetaminophen

is a derivative of acetamide, which in 1992 replaced aspirin as the top-selling over-the-counter pain reliever.

Barbiturates

which are cyclic amide compounds, are a heavily used group of prescription drugs that cause relaxation (tranquilizers), sleep (sedatives), and death (overdoses).

•Amides

__ do not exhibit basic properties in solution as amines do.

Methanamide and its N-methyl and N,N-dimethyl derivatives

are all liquids at room temperature.

Amides

__ are the least reactive of the common carboxylic acid derivatives and they can be synthesized from an acid chloride, an acid anhydride, an ester, or the carboxylic acid itself

acid–base reaction

__ when a 1 amine is the reactant

acid–base reaction

occurs in which a carboxylic acid salt is produced

amidification reaction

is the reaction of a carboxylic acid with an amine (or ammonia) to produce an amide.

carboxylic acid

—OH group is lost from the __

ammonia or amine

—H atom is lost from the __

water

__ is formed as a by-product

Amidification reactions

__ are thus condensation reactions.

amide hydrolysis

the bond between the carbonyl carbon atom and the nitrogen is broken, and free acid and free amine are produced.

Amide hydrolysis

is catalyzed by acids, bases, or certain enzymes; sustained heating is also often required.