W17: AMINES AND AMIDES

Nitrogen is a member of _________ of the periodic table.

Group VA

Nitrogen has ____________ and will form __________________ to complete its octet of electrons.

1.) five valence electrons
2.) three covalent bonds

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

amine

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

Primary amine

The generalized formula for a primary amine is _______.

RNH2

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

Secondary amine

The generalized formula for a secondary amine is ______.

R2NH

A _________ 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 tertiary amine is ____.

R3N

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

Tert-butyl alcohol

__________________ possess substituted amino groups.

Secondary and tertiary amines

Suffix of amine IUPAC naming

-amine

Other simple aromatic amines are named as derivatives of _______.

aniline

In secondary and tertiary aromatic amines, the additional group or groups attached to the nitrogen atom are located using a capital ___.

N-

are gases at room temperature and have ammonia-like odors

1.) methylamines
2.) ethylamine

have odors resembling that of raw fish

liquid amines

have strong, disagreeable odors

diamines

Odoriferous compounds found in amines

1.) diamines putrescine
2.) cadaverine

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

simpler amines

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

Aromatic amines

The boiling points of amines are intermediate between those of ______ and _____ of similar molecular mass.

1.) alkanes
2.) alcohols

The boiling points of amines are lower than those of ___________________.

corresponding alcohols

Amines with ____________________ are infinitely soluble in water.

fewer than six carbon atoms

Even ________ amines are water-soluble

tertiary

a chemical substance that is released at the end of a nerve

Neurotransmitter

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

Norepinephrine

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

Dopamine

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

Serotonin

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

Epinephrine

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

Histamine

is a nitrogen-containing organic compound extracted from plant material

Alkaloids

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

Morphine

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

Codeine

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

Heroin

Preparation of Amines:

• Alkylation in the presence of ______.

base

Alkylation under basic conditions is actually a ________ process.

two-step

using a primary amine preparation as an example, an amine salt is produced

first step

involves the base present (NaOH), converts the amine salt to free amine.

Second step

Tertiary amines react with alkyl halides in the presence of a strong base to produce a ___________________.

quaternary ammonium salt

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

quaternary ammonium salt

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

Amides

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

Primary amide

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

Secondary amide

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

Tertiary amide

has a hydrogen atom attached to an unsubstituted amide functional group

simplest amide

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

simplest aromatic amide

Cyclic amide structures are _____.

possible

Cyclic amides are called ________, a term that parallels the
use of the term lactones for cyclic esters.

lactams

A lactam with a five-membered ring is a _________.

y-lactam

The members of the _____________ have structures that contain a b-lactam ring.

penicillin family of antibiotics

The simplest aromatic amide, a benzene ring bearing an unsubstituted
amide group, is called ___________.

benzamide

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

Urea

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

uremia

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

Melatonin

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

Acetaminophen

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

Barbiturates

Amides do not exhibit __________ in solution as
amines do.

basic properties

are all liquids at room temperature.

1.) Methanamide
2.) N-methyl
3.) N-dimethyl derivatives

In many cases, the amide melting point is even
_______ than that of the corresponding carboxylic acid.

higher

The high melting points result from the numerous
______________________ possibilities that exist between
amide H atoms and carbonyl O atoms.

intermolecular hydrogen-bonding

Fewer hydrogen-bonding possibilities exist for ________
because the nitrogen atom now has only one hydrogen atom;
hence lower melting points are the rule for such amides

2* amides

Amides of __________________, are soluble in water.

5 or 6 carbon atoms

Amides are the ___________ of the common carboxylic acid
derivatives.

least reactive

The reaction of a __________ with ________ or a __________
produces an amide, provided that the reaction is carried out at an
__________ and a _______ agent is present.

1.) carboxylic acid
2.) ammonia
3.) 1 or 2 amine
4.) elevated temperature (greater than 100 C)
5.) dehydrating

Preceding reactions are run at room temperature (25OC),
no amide formation occurs; instead an ____________
occurs in which a __________ is produced.

1.) acid–base reaction
2.) carboxylic acid salt

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

amidification reaction

In amidification, an ______ is lost from the carboxylic acid, a ______ is lost
from the ammonia or amine, and ______ is formed as a by-product.

1.) —OH group
2.) —H atom
3.) water

Amidification reactions are thus _______________.

condensation reactions

In amide _______, the bond between the carbonyl carbon atom and the nitrogen is
broken, and ________ and _______ are produced.

1.) hydrolysis
2.) free acid
3.) free amine

Amide hydrolysis is catalyzed by ____________________; sustained _______
is also often required.

1.) acids, bases, or certain enzymes
2.) heating