Organic - Chapter 6: Amines & Amides

nitrogen

nitrogen

Amines and amides contain _______.

medicines

The effectiveness of a wide variety of important __________ depends on the presence of the nitrogen-containing group.

amino acids, proteins, nucleic acids

Both amines and amides are abundant in nature and play crucial roles in the biochemistry of life (__________, ________, __________)

Amines

Organic derivatives of ammonia in which one or more of the hydrogens are replaced by an organic group.

NH3

Formula of Ammonia

Primary Amines

The N atom is bonded to one R group.

Secondary Amines

The N atom is bonded to two R groups.

Tertiary Amines

The N atom is bonded to three R groups.

common names

In amine nomenclature, _____________ are used extensively for compounds with low molecular weights.

False

T or F: Amines are the top priority when naming organic compounds.

Aniline

Simplest Aromatic Amine

gases

Low molecular weight animes are _______ at room temperature. Heavier (more complex) amines are liquids or solids.

True

T or F: The N-H bond is not quite as polar as the O-H bond.

hydrogen bonds

Primary and Secondary amines can form _____________ between molecules (like alcohol).

lower

The hydrogen bonds formed between amine molecules are not as strong as those of alcohols, so amine boiling points are somewhat ______ than those of alcohols.

Tertiary

________ amines cannot form hydrogen bonds with themselves because the nitrogen has no attached H atom.

True

T or F: Tertiary amines have a similar boiling point to alkanes that have about the same molecular weight.

water soluble

Amines can hydrogen bond with water, making smaller amine molecules (less than six carbons) _____________.

ammonia

Low molecular weight amines have a sharp and penetrating odor similar to _________.

decaying fish

Larger amines smell like __________.

Putrescine

(1,4-diaminobutane) Larger amine molecule that smells like decaying fish.

Cadaverine

(1,5-diaminopentane) Larger amine molecule that smells like decaying fish.

organic bases

Amines are the most common _____________.

weak bases

All amines behave as _________ in water (similar ro NH3).

Bronsted bases

When _________ like ammonia reacts with water, they liberate OH- ions.

Ammonium ion + OH-

Results of adding amines with H2O.

Salt

Results of amines and HCl.

Amide + HCl

Results amines and acid chloride.

Amide + Carboxylic Acid

Results of amine and acid anhydride.

True

T or F: The same amines that react with hydrochloric acid, also reacts with other acids such as sulfuric, nitric, phosphoric, and carboxylic acids.

Amine Salts

___________ are named by changing "amine" to "ammonium" and adding the anion name (from the acid).

ionic compounds

Amine salts have physical properties of other ________________.

crystalline solids

Amine salts are white ____________ with high melting points.

parent amine

Because amine salts are ionic, they are more water soluble than their _____________.

strong base

Amine salts are easily converted back to amines by adding a __________.

pH dependent

The form in which amines occur in solutions is _____________.

Low pH

High H+ (_______) favors the amine salt.

High pH

High OH- (______) favors the amine.

amine cations

The _____________ in salts can have one, two, or three R groups attached to the Nitrogen.

False

T or F: It is not possible to have amine cations in which four R groups are attached.

Quaternary Ammonium Salts

Amine cations in which four R groups are attached, and contain no hydrogen that can be removed by a base.

pH independent

Since no hydrogen can be removed from quaternary ammonium salts, they only have one form so they are _____________.

Choline Cation

Important quaternary ammonium ion in biochemistry.

Acetylcholine Cation

Important quaternary ammonium ion in biochemistry.

disinfectant

Some quaternary ammonium salts have __________ properties.

Benzalkonium Chloride

(Zephiran) Well known antiseptic. Its detergent action destroys the membranes that coat/protect microorganisms (it is used prior to surgery to disinfect hands/instruments).

Amides

Organic compounds that contain a functional group with a carbonyl attached to a nitrogen.

Amide Linkage

The single bond linking the carbonyl carbon and nitrogen atoms in the group.

carboxylic acid

Amides may be thought of as containing an ammonia or amine portion and a portion derived from a ________________.

reactive

The reaction of an amine with a carboxylic acid usually produces a salt and not an amide. Therefore, the preparation of amides requires the more _______ acid chlorides and anhydrides.

True

T or F: While both primary and secondary amines can form amides, but tertiary amines do not react to form amides.

Polyamides

Condensation polymers, produced by the reaction of diacid chlorides with diamines. The repeating units are held together by amide linkages (i.e. formation of nylon).

3 Billion

_________ of nylon and related polyamides are produced annually.

60%

About ____ of that is used in home furnishings such as carpet. The rest is used to make clothing and tire cords.

tubing, sutures

In medicine, nylon is used in specialized ________ and _________.

Proteins

Polymers (polyamides) made up of monomers of amino acids (amine group with a carboxylic acid group).

protein chains

Amide linkages are characteristics of ___________.

Neurotransmitters

The chemical messengers of the nervous system which carry nerve impulses from one nerve cell (neuron) to another.

synapse

Neurons (dendrite, soma, axon, synaptic terminals) are separated by a small gap called the _______.

axon

Molecules of a neurotransmitter are stored in small pockets in the _____ near the synapse.

synaptic terminal

The pockets release neurotransmitter molecules into the synapse when an electrical current flows from the soma, along the axon to the _____________.

electrical current

The _____________ is generated by the exchange of positive and negative ions across membranes.

dendrites

The released molecules diffuse across the synapse and bind to receptors on the ________ of the next neuron. Once the message has been delivered, the receiving cell sends it on to the next nerve cell.

Central Nervous System

In the _______________ (brain & spinal cord) the most important molecules are amines.

moods

Neurotransmitters are not only chemical messengers, they are also partly responsible for our _______.

norepinephrine, serotonin

A simplified biochemical theory of mental illness is based on two amines found in the brain: ______________ and ________.

Norepinephrine

Synthesized from tyrosine (which converts to dopa and then dopamine), associated with depression and manic states.

Serotonin

Synthesized from tryptophan, found to influence sleeping, the regulation of body temperature, and sensory perception.

Drugs

_______ that mimic serotonin are often used to treat depression, anxiety, and OCD.

Epinephrine

(Adrenaline, Fight-or-Flight hormone) has a molecular structure or norepinephrine plus an N-methyl group, more important as a hormone than a neurotransmitter.

adrenal gland

Epinephrine is synthesized in the ____________ and acts to increase the blood level of glucose for energy. Also provides a sudden burst of energy released in response to pain, anger, or fear.

Amphetamine

(STP, speed, mescaline, meth, etc.) Powerful nervous system stimulant with an amine structure similar to epinephrine. Has severe detrimental effects on the body and mind.

Methamphetamine

Used legally and illegally to elevate mood or reduce fatigue.

Alkaloids

Class of nitrogen-containing organic compounds obtained from plants.

True

T or F: Plants are the sources of some of the most powerful drugs known.

Nicotine

Found in tobacco and used a stimulant in cigarettes, cigars, and chewing tobacco. It is not harmful but it is very addicting.

Caffeine

Found in coffee, soft drinks, chocolate, and tea. I used as a central nervous system stimulant. Not harmful but very addicting.

Quinine

Used to treat malaria.

Atropine

Used as a preoperative drug to relax muscles and reduce saliva secretions (can also be used by eye doctors to dilate pupils).

Opium

Used to make codeine (in cough medicines), morphine (pain killer), and heroin.

Formamide

The only unsubstituted amide that is a liquid, all others are solids with high melting points.

Unsubstituted Amides

________________ can form a complex network of intermolecular hydrogen bonds.

reduces, decreases

The substitution of a R group on the nitrogen ________ the number of intermolecular hydrogen bonds that can form thus causing melting points to __________.

shape

The hydrogen bonding of amides is important in maintaining the _______ of protein molecules.

six

Amides with fewer than _____ carbon atoms are soluble in water due to their ability to hydrogen bond.

carbonyl oxygen

Even substituted amides are soluble because the _________________ can hydrogen bond.

Amide Neutrality

Amides are neither acidic nor basic. The carbonyl group bonded to the nitrogen destroys the basicity of the original amine, and the nitrogen of the amine replaces the acidic -OH of the carboxylic acid.

Amide Hydrolysis

The reverse of the amide formation reaction where an amide is cleaved to produce a carboxylic acid and an amine or ammonia.

ester hydrolysis

As with ______________, amide hydrolysis requires a strong acid or a strong base.

catalyst

The _______ used determines the final product.

acidic conditions

Under _______________ the amine salt is produced along with the carboxylic acid.

basic conditions

Under ________________ the carboxylate salt is produced along with the amine.

salt

The form in which carboxylic acids and amines occur in solution depends on pH, one of the hydrolysis products must always be in the form of a ______.

Thiopental

(Pentothal) Intravenous Anesthesia

Amobarbital

(Amytal) Treatment of insomnia.

Diazepam

(Valium) Tranquilizer

Ampicillin

(Polycillin) Antibiotic

Acetaminophen

Drug for minor pain.

Ibuprofen

Drug for minor pain.

True

T or F: Jaedyn is awesome for making all of these study sets.