Transcript File chapter 5 alcohols, ethers and thiols

FOCUS ON ALCOHOLS
-OH functional group
-nomenclature of alcohols
-methanol
-ethanol
-isopropyl
-menthol
-ethylene glycol
-glycerol
-phenols
-ethers
-longest chain has OH group
-suffix "ol" used for OH group and must have
lowest possible number
-both IUPAC and Common names typical for alcohols,
students must learn both for most common alcohol
examples.
• Alcohols
– An alcohol has a hydrogen replaced by a hydroxyl (-OH) group.
– The name of the hydrocarbon that was substituted determines the
name of the alcohol.
– The alcohol is named using the hydrocarbon name and adding the
suffix –ol.
• If methane is substituted with an OH group it becomes
methanol
• If a pentane group is substituted with an OH group it is
pentanol.
• For alcohols with more than two carbon atoms we need the
number the chain so as to keep the alcohol group as low as
possible.
• Four different alcohols. The
IUPAC name is given above each
structural formula, and the
common name is given below.
– The OH group is polar and short chain alcohols are
soluble in both nonpolar alkanes and water.
– If an alcohol contains two OH groups it is a diol
(sometimes called a glycol).
– An alcohol with three OH groups is called a triol
(sometimes called a glycerol).
• Common
examples of
alcohols with one,
two, and three
hydroxyl groups
per molecule. The
IUPAC name is
given above each
structural
formula, and the
common name is
given below.
Lab: Properties of Alcohol
• Objective: To determine the density and boiling
point of alcohol.
• Results: Density: Data table-% error calc.(.789 gr/mL)
•
Boiling: Boiling temp-% error calc.(78.40C)
• Discussion:
• Paragraph 1: Explain basic info on alcohols/properties…see
textbook for info.
• Paragraph 2: Explain density/how-why technique/sources of
error
• Paragraph 3: Explain boiling point in detail/how-why of
technique/sources of error.
-wood alcohol
-very toxic (15 mls. blindness and 30 mls.
death if ingested
-oxidizes to formaldehyde and then to formic
acid in the body (as to alcohols in general)
-uses: paints, shellacs,varnishes
-Treatment for methanol poisoning
Formula:
C-OH
Ethanol or Ethyl
Alcohol
ALCOHOLIC BEVERAGES
-99% water and ethanol 1%congeners
-flavor from congeners, such as juniper berries (gin)
-alcohol beverage
-grain alcohol
-alcoholism
Formula: C-C-OH
-before distillation, 13% highest since yeast cannot survive if higher. (1200 A.D.)
-more tolerant yeast? WEBSITE
-% x 2 = proof
-yeast ferment sugar to alcohol + carbon Dioxide
-denatured alcohol to prevent taxes
How Alcohol Enters
the Body
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Alcohol Effects:
Men vs. Women
When you compare men and women of the same height, weight and build, men tend to
have more muscle and less fat than women. Because muscle tissue has more water than
fat tissue, a given dose or amount of alcohol will be diluted more in a man than in a
woman. Therefore, the blood alcohol concentration resulting from that dose will be
higher in a woman than in a man, and the woman will feel the effects of that dose of
alcohol sooner than the man will.
When a person drinks an alcoholic beverage, about 20 percent of the alcohol is absorbed
in the stomach and about 80 percent is absorbed in the small intestine. How fast the
alcohol is absorbed depends upon several things:
The concentration of alcohol in the beverage - The greater the concentration, the faster
the absorption.
The type of drink - Carbonated beverages tend to speed up the absorption of alcohol.
Whether the stomach is full or empty - Food slows down alcohol absorption.
After absorption, the alcohol enters the bloodstream and dissolves in the water of the
blood. The blood carries the alcohol throughout the body. The alcohol from the blood
then enters and dissolves in the water inside each tissue of the body (except fat tissue, as
alcohol cannot dissolve in fat). Once inside the tissues, alcohol exerts its effects on the
body. The observed effects depend directly on the blood alcohol concentration (BAC),
which is related to the amount of alcohol consumed. The BAC can rise significantly
within 20 minutes after having a drink.
Alcohols oxidizes to Aldehydes
Alcoholism
• -alcohol -- aldehyde--other products
• -Specific aldehyde: acetaldehyde (ethanal)
• makes one sick if build-up in body
• -Disulfuram will keep acetaldehyde in body if alcohol
taken in so person gets sick when they drink, so negative
feeling hopefully discourages person to drink.
• Most Recently: Focus on neurotransmitters and their role
in addiction
Alcohol and the Brain-website
• The centers are not equally affected by the same BAC - the
higher-order centers are more sensitive than the lowerorder centers. As the BAC increases, more and more
centers of the brain are affected.The order in which alcohol
affects the various brain centers is as follows:
• Cerebral cortex
• Limbic system
• Cerebellum
• Hypothalamus and pituitary gland
• Medulla (brain stem)
Neurotransmitters are chemicals that are used to
relay, amplify and modulate electrical signals between a
neuron and another cell.
An action potential stimulates the synaptic vesicles to
send the neurotransmitters to the cell membrane. They
are released and then bind to the receptors of the next
cell in order to transfer the “message”
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Alcoholism is the consumption of or
preoccupation with alcoholic beverages to the
extent that this behavior interferes with the
alcoholic's normal personal, family, social, or work
life. An alcoholic can develop multiple forms of
addiction to alcohol simultaneously such as
psychological, metabolic, and neurochemical.
Each type of addiction must be treated individually
for an alcoholic to fully recover.
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The mechanism of alcoholism appears to be
irregularities in the brain's neurotransmitters, the
messenger substances that regulate behavior. Addiction
occurs when there is an imbalance that affects neurons
in the brain's "reward" areas.
When the brain is unable to produce the required levels
of chemicals naturally, an individual often learns to selfmedicate with alcohol and other substances. The opioid
(a neurotransmitter) levels determine of “normal” a
person feels.
Opioids are the neurotransmitters responsible for
making people feel good and comfortable. Its also found
in drugs such as opium as opiods are commonly used
as pain relievers and anti-depressants.
Alcohol produces "tetrahydroisoquinolines" or TIQ's. TIQ's
closely resemble opioids so they "trick" the brain into
thinking this individuals opioid levels are normal.
The alcoholic now feels good. The "uncomfortable" feeling is
gone.
The more alcohol this person consumes, the more the brain
is tricked into thinking the opioid level is normal because of
the presence of the TIQs.
When TIQs are present, the brain signals the manufacturing
cells to stop producing any more opioids (which were not
enough to begin with).
The more these Manufacturing Cells are inactive, they die,
which means EVEN LESS opioids are produced.
Now the alcoholic has to consume even more alcohol to get
rid of the "uncomfortable" feeling. A vicious cycle.
In order to partially treat alcoholism, scientists
believe restoring the natural levels of opioids and
restoring the neurotransmitters killed by
inactiveness will help cure the disease.
However, the patient also must submit to
abstinence from alcohol and improved nutritional
intake.
Therefore the patient can quickly begin to restore
the levels of opioids and allow him to function more
normally to improve their life and lifestyle alcohol
free.
Does “Chaser” work?
What is it?
website
- known as "rubbing alcohol"
-cools skin by evaporation
-”dry gas” additive for gasoline (although
ethanol also used)
Dry gas is basically alcohol, ethanol to be specific. The ethanol mixes
with the water and keeps it from freezing when the temperature drops and makes it burnable. So yes, it does serve
a very useful function. The engine doesn't matter. It could be a little three cylinder Geo Metro or the V-16 Cadillac.
Condensation will still form in the gas tank and you will need the dry gas to keep it from freezing so it can be
burned.
The only place where dry gas would not help is in areas that require a 10% ethanol/gasoline blend which, in
essence, puts in one gallon of dry gas in every ten gallons of gasoline.
-used as an astringent (hardens skin and
decreases pore size so limits secretions,
making it easy to clean skin of cosmetics)
-minty odor
-shaving cream, cough
drops,("mentholated"), cigarettes,
toothpaste
-viscous, toxic, sweet-tasting
-antifreeze for automobile radiators because:
-lowers freezing point and increases boiling
point of water, inexpensive,soluble in water,
noncorrosive to metals,
-IUPAC name: 1,2 ethanediol
-toxic effects website
Antifreeze Info.
• Ethylene glycol is the ingredient that makes antifreeze
tasty. Though colorless and odorless, the syrupy alcohol
derivative—which is excellent at lowering the freezing
points of vital engine fluids—has a sweet taste that jibes
well with soda, juice, and other sugary beverages. As many
concerned pet owners and parents are well aware, dogs,
cats, and kids are prone to lap up puddles of antifreeze left
on garage floors. Every year, 90,000 animals and 4,000
children ingest the toxic liquid; if not treated immediately,
the consequences of the poisoning can include renal or
cardiovascular failure, brain damage, and death.
Automobile’s Cooling System
• Radiator
• http://auto.howstuffworks.com/coolingsystem.htm
-also known as glycerin
- IUPAC: 1,2,3 propanetriol
-sweet, nontoxic, lubricant
- used as moistening agent for cosmetics
-used in nitroglycerin preparation
-More glycerin uses website
Diatomaceous Earth
website
• Activity: Create/View slide of Diatomaceous Earth
-contain OH directly attached to aromatic ring
-initially used as antiseptics
-since this is burning to healthy tissue, replacements
have been found to be used in mouthwashes, etc.
-Phenol has antiseptic properties, and was used by
Sir Joseph Lister in his pioneering technique of
antiseptic surgery, though the skin irritation caused
by continual exposure to phenol eventually led to the
substitution of aseptic (germ-free) techniques in
surgery. It is one of the main components of the
commercial antiseptic TCP (trichlorophenol).
Phenol has anesthetic properties, and is the active
ingredient in some oral anesthetics such as
Chloraseptic spray
Ethers
Ether as General Anesthetic
Ether history website
Diethyl Ether
• Diethyl Ether, well-known general
anesthetic, commonly called simply ether,
an organic compound belonging to a large
group of compounds called ethers. Ethyl
ether is best known as an anesthetic. A
highly volatile liquid, it is also used as a
solvent, an extractant, and a reaction
medium.
Thiols
Neutralizing the smell website
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Skunk defensive secretion is composed of seven major volatile components.
These can be divided into two major groups of compounds, thiols and acetate
derivatives of these thiols. Two of the thiols are responsible for the strongly
repellent odor of the secretion, (E )-2-butene-1-thiol and 3-methyl-1butanethiol. The third thiol, 2-quinolinemethanethiol, is not as odoriferous due
to its low volatility and the fact that large thiols do not trigger the human
olfactory receptor. The chemical structure of these compounds and their
percent (four individuals) in the defensive secretion are shown in the following
illustration
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