Organic - Chapter 6: Amines & Amides

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Amines and amides contain _______.
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 (__________, ________, __________)
Organic derivatives of ammonia in which one or more of the hydrogens are replaced by an organic group.
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.
T or F: Amines are the top priority when naming organic compounds.
Simplest Aromatic Amine
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Low molecular weight animes are _______ at room temperature. Heavier (more complex) amines are liquids or solids.
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).
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.
________ amines cannot form hydrogen bonds with themselves because the nitrogen has no attached H atom.
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) _____________.
Low molecular weight amines have a sharp and penetrating odor similar to _________.
decaying fish
Larger amines smell like __________.
(1,4-diaminobutane) Larger amine molecule that smells like decaying fish.
(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.
Results of amines and HCl.
Amide + HCl
Results amines and acid chloride.
Amide + Carboxylic Acid
Results of amine and acid anhydride.
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.
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.
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Acetylcholine Cation
Important quaternary ammonium ion in biochemistry.
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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).
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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 ________________.
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.
T or F: While both primary and secondary amines can form amides, but tertiary amines do not react to form amides.
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.
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 _________.
Polymers (polyamides) made up of monomers of amino acids (amine group with a carboxylic acid group).
protein chains
Amide linkages are characteristics of ___________.
The chemical messengers of the nervous system which carry nerve impulses from one nerve cell (neuron) to another.
Neurons (dendrite, soma, axon, synaptic terminals) are separated by a small gap called the _______.
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.
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.
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 ________.
Synthesized from tyrosine (which converts to dopa and then dopamine), associated with depression and manic states.
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Synthesized from tryptophan, found to influence sleeping, the regulation of body temperature, and sensory perception.
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_______ that mimic serotonin are often used to treat depression, anxiety, and OCD.
(Adrenaline, Fight-or-Flight hormone) has a molecular structure or norepinephrine plus an N-methyl group, more important as a hormone than a neurotransmitter.
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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.
(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.
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Used legally and illegally to elevate mood or reduce fatigue.
Class of nitrogen-containing organic compounds obtained from plants.
T or F: Plants are the sources of some of the most powerful drugs known.
Found in tobacco and used a stimulant in cigarettes, cigars, and chewing tobacco. It is not harmful but it is very addicting.
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Found in coffee, soft drinks, chocolate, and tea. I used as a central nervous system stimulant. Not harmful but very addicting.
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Used to treat malaria.
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Used as a preoperative drug to relax muscles and reduce saliva secretions (can also be used by eye doctors to dilate pupils).
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Used to make codeine (in cough medicines), morphine (pain killer), and heroin.
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 __________.
The hydrogen bonding of amides is important in maintaining the _______ of protein molecules.
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.
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.
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 ______.
(Pentothal) Intravenous Anesthesia
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(Amytal) Treatment of insomnia.
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(Valium) Tranquilizer
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(Polycillin) Antibiotic
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Drug for minor pain.
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Drug for minor pain.
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