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O Chem Test 2
DO THE JIGGEY WIGGEY
46
Organic Chemistry
Undergraduate 3
11/05/2010

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Term
FAS Perspective (6)
Definition
Mothers are tested on their first visit to the obstetrician for previous infectious diseases. Mothers are then given advice regarding diet & nutrition and told to stay away from alcohol.

The use of alcoholic beverages by a pregnant woman can cause fetal alcohol syndrome (FAS) which induces mental retardation, poor growth before and after birth, and facial malformations.

Even when mothers only drink socially, the fetus is still affected and may have fetal alcohol effects which include reduced birth weight, some learning disabilities, and behavioral problems.

Alcohol crosses the placenta and within 15 min the fetus BAC is as high as the mothers. While the mother has enzymes to detoxify the alcohol, the fetus does not.

Alcohol can cause cell division to stop or be radically altered. It is thought that even a single night out drinking could be enough to cause FAS if it occurs during a critical development period.

Because there is evidence that suggests that there is a risk if even only an ounce of 100% alcohol each day has its risks, the AMA and Surgeon General recommend that pregnant women abstain from drinking.
Term
Drinking and Driving Perspective (4)
Definition
41,000 people are killed a year via alcohol-related car accidents because BAC of .05-.15% significantly inhibit coordination. Over .08% is intoxication in most states. BAC of .30-.50% cause unconsciousness and risk of death.

The breathalyzer test prevents and gathers evidence at the scene of the accident. The suspect must exhale into a solution that will change color from yellow-orange to green with reduction catalyzed by alcohol.

The solution is acidic [Cr2O7]2- ion and the the alcohol reduces the chromium from +6 (yellow-orange) to +3 (green). The intensity of the green is proportional to the amount of ethanol that was oxidized.

If the breathalyzer test is positive, a more accurate blood test is then given to establish guilt or innocence. The breathalyzer continues to provide a field-level screen for those who choose to drink and drive.
Term
IUPAC Name: Methanal

Common Name: ________
Definition
Formaldehyde
Term
IUPAC Name: Ethanal

Common Name: ________
Definition
Acetaldehyde
Term
IUPAC Name: Propanal

Common Name: ________
Definition
Propionaldehyde
Term
IUPAC Name: Butanal

Common Name: ________
Definition
Butyraldehyde
Term
IUPAC Name: Pentanal

Common Name: ________
Definition
Valeraldehyde
Term
6 or Fewer Carbon Chain alcohols are different from longer chained ones because...
Definition
They are soluble due to intermolecular hydrogen bonds. 1-4 is very soluble, 5-6 C's have medium solubility, 7 or more are nearly insoluble.
Term
The name of the compound that tastes like...
Almmonds
Vanilla Beans
Cinnamon
Lemongrass
Berries
Mushrooms
Definition
Benzaldehyde
Vanillin
Cinnamaldehyde
Citral
Demascone
2-Octanone
Term
Formaldehyde and Methanol Poisoning Perspective (6)
Definition
Most aldehydes are unpleasant and don't smell good. Formalin, formaldehyde in aqueous solution, is used for embalming, but never as an antiseptic because of its toxic fumes and skin irritations.

Formaldehyde has use in vaccines because it kills the RNA and denatures proteins so that virus replication is impossible (risk free) but the proteins essential for antibody production remain intact so that the body can still produce antibodies.

Formaldehyde can also be produced in the body via the enzyme alcohol dehydrogenase which detoxes alcohols via oxidation, converts methanol to formaldehyde. Formaldehyde then reacts with cellular macromolecules like proteins causing severe damage.

Methanol poisoning can cause blindness, respiratory failure, convulsions, and even death.

To combat methanol poisoning, medical doctors rely on the competitive inhibition provided from excess amounts of ethanol to slow the conversion from methanol to formaldehyde enough so that the body can rid itself of methanol without its conversion. This is done by replacing methanol conversion with ethanol's conversion to a less toxic substance than formaldehyde: acetaldehyde.

The molecule in higher amounts will bind to the dehydrogenase enzyme more frequently, inhibiting the absorption of the other.
Term
Alcohol Abuse and Antabuse Perspective (4)
Definition
Each year 75,000 people die from alcohol abuse. Of them 35,000 died of cirrhosis, cancer, or other alcohol diseases. 41,000 die in automobile accidents. 1,400 college students die each year due to alcohol. These numbers make alcohol the third biggest cause of preventable deaths in the US.

Tetraethylthiuram Disulfide (Disulfiram) or Antabuse has been used since 1951 to prevent people from consuming alcohol because it makes them violently sick if any is consumed. Acetaldehyde dehydrogenase typically oxidizes acetaldehyde to ethanoic acid (acetic acid) which is then used metabolically, but antabuse inhibits acetaldehyde dehydrogenase.

Acetaldehyde is responsible for many hangover symptoms, and its lack of conversion causes severe sickness as acetaldehyde levels reach 5 to 10 times higher than normal.

These unpleasant sympoms may last for hours, and while they make for an effective deterrent, they typically are not enough to stop alcohol abuse in individuals who need help.
Term
Golden Tan Without the Fear of Skin Cancer Perspective (6)
Definition
The sun is linked to skin cancer, but people still want their tans.

The active ingredient in most self-tanners is Dihydroxyacetone CH2OHCOCH2OH or DHA. It is a ketone and a sugar or keto sugar.

DHA was originally found by a doctor tying to help children be able to store glycogen. The children spit up the DHA onto the doctors skin and she noticed it caused tanning to occur. This happens because DHA forms melanoids when in contact with keratins.

Originally tans were orangey, but they're better now that more pure DHA is used, it penetrates deeper, and the reaction medium is a pH of 5. The reaction that occurs is between DHA's carbonyl group, and free amino groups (-NH3+).

Gentle exfoliation before tanning allows for a more even tan because there is less keratin and less reactant in certain parts of the stratum corneum.

Overall self-tans make a good real sun substitute when it comes to looking tan.
Term
Benedicts Test
Definition
Cu(OH)2 and sodium citrate react to oxidize aldehydes but not ketones. Cu2+ is reduced to Cu+ and it precipitates as Cu2O which is red.

This works on glucose because all simple sugars are either aldehydes or ketones, and glucose is an aldehyde which is oxidized to a caboxyllic acid.
Term
Aldehydes and Ketones can be Hydrogenated to...
and what catalyst is required?
Definition
Alcohol, the CO double bond opens up and accepts the H2 molecule.

Pt is required as a catalyst.
Term
Complete the rxn: R-SH + R-SH --[O]-->
<--[R]--
What type of reaction is this?
Definition
R-S-S-R + 2H+ 2e-

The reaction is generally an oxidation reaction, and specifically condensation reaction.
Term
What is a phenol?
Definition
A benzene ring with an -OH attached to it.

Note: Phenols are acidic.
Term
Zaitsev's Rule
Definition
In an elimination reaction, the alkene with the greatest number of alkyl groups on the double-bonded carbon, or the more highly substituted alkene, is the major product of the reaction. (there is still a minor product!)
Term
What is a flavonoid? (3)
Definition
Any of many compounds that are plant metabolites, being formally derived from flavone. They are soluble colored compounds. All polyphenols are flavonoids.
Term
Flavone
Definition
a three benzene ring structure with two oxygens in the middle ring. One of which connecting two carbons, the other being directly across the ring is double bonded to a carbon in the ring.
Term
What is a hydroxyl group?
Definition
The signature molecule of an alcohol -OH
Term
What are the terms for a compound with two hydroxyl groups, and three hydroxyl groups?
Definition
-diol and -triol

Would be used as such: Instead of one hydroxyl group of Ethanol, you would have Ethanediol or Ethanetriol, subsequently naming 1 or 2 to indication the location of the hydroxyl groups.
Term
IUPAC System for Alcohols (6)
Definition
-Determine the parent compound name
-Replace the e ending with -ol
-Number the chain to give the hydroxyl group the lowest possible number
-Name and number all substituents and add them as prefixes to the alkanol name
-add diol or triol as appropriate for 2 or 3 hydroxyl groups
Term
Oxidation of a primary alcohol will give you an...

Secondary Alcohol...

Tertiary Alcohol...
Definition
Aldehyde

Ketone

not react
Term
Hydration of an alkene will get you an...
Definition
Alcohol
Term
Dehydration of an alcohol will get you...

and requires what as a catalyst?
Definition
An alkene and a water molecule

it requires H+ and heat
Term
Why is aspartame so bad for your health?
Definition
Aspartame is broken down in the body and forms methanol as one of its products which is then oxidized in the liver to formaldehyde.
Term
Oxidation in order starting with alkane
Definition
Alkane gets oxidized to --> Alcohol --> Aldehyde --> Carboxylic acid

This order is then reversed for reduction.
Term
IUPAC Name: 1,2,3 Propanetriol

Common Name: _______
Definition
Glycerol
Term
IUPAC Name: Dimethyl Ether

Common Name: _______
Definition
Methoxy Methane
Term
Tautomer
Definition
Tautomers are isomers of organic compounds that readily interconvert by a chemical reaction called tautomerization. It is common that this reaction results in the formal migration of a hydrogen atom or proton, accompanied by a switch of a single bond and adjacent double bond.

C2H4O has 2 tautomers that are in equilibrium: ethanal and ethEnol (an enol)
Term
What is an Aldol Condensation rxn?

What catalyst is required?
Definition
Self-addition rxn that is very complex

Basic Medium OH- as a catalyst

Ethanal + Ethanal <--Basic Medium--> 3-Hydroxybutanal
Term
IUPAC Naming for Ether groups and mid-chain ethers
Definition
CH3-O-R is methoxy, CH3-CH2-O- is ethoxy

two of the same group makes for di- prefix, ie: diethyl ether [ethyl-O-ehtyl]

CH3-O-CH2CH3 can either be [by size Methyl Ethyl Ether], or [alphabetically Ethyl Methyl Ether]
Term
Why/how will formaldehyde make you go blind?
Definition
Formaldehyde replaces retinal in light reception in the eye.
Term
Dehydration Synthesis of an Ether
Definition
R1-OH + R2-OH --H+ & Heat--> R1-O-R2 + H2O
Term
Order in which ethers, alcohols, aldehydes, and ketones will more dramatically affect Boiling Point (from lower bp's to higher)
Definition
Alkane (no groups), Ether, Aldehyde, Ketone, Alcohol, Carboxyllic Acid
Term
What are the four greek letters we need to know?
Definition
Alpha, Beta, Gamma (looks like a y), and Delta (looks like a Christmas ornament)
Term
IUPAC Name: Propanone

Common Name: ________
Definition
Acetone
Term
Naming Ketones via Common Name
O
CH3CH2CH2CH2-C-CH2CH2CH3

Would be 4 Octanone IUPAC

Common Name?
Definition
Butyl Propyl Ketone
Term
Why does fructose react with Benedict's reagent?
Definition
Because fructose has a primary alcohol that can be oxidized and dehydrogenated to an aldehyde, and a ketone that is reduced/hydrogenated to an alcohol, and when this happens, the former fructose molecule becomes glucose which then reacts with Benedict's reagent.
Term
Common Names(2) for 1,2 Ethanediol
Definition
Ethylene Glycol or Anti-Freeze
Term
Common Name for 2-Propanol
Definition
Isopropyl Alcohol, it is in essence (not named as) Rubbing Alcohol
Term
O O NADH -->
CH3-C-C-O- --Lactate Dehydrogenase->
(Pyruvate)
Definition
NAD+
OH O
CH3- C - C - O- (Lactate)
H
Term
What reactions happen when ethanol reaches the liver?
Definition
Ethanol-->Ethanal-->Ethanoic Acid-->CO2 & H20
Term
What happens during fermentation of glucose?
Definition
C6H12O6 is enzymatically broken down through several steps to 2 Ethanol Molecules and 2 CO2 molecules.
Term
Alcohol --H+, Heat-->
Definition
Alkene + H20

Dehydration of an alcohol, requires -OH to not be at the end of a alkane
Term
H+
R-OH + R-OH ------>
Heat
Definition
Dehydration Synthesis of an Ether R-O-R + H2O
Requires -OH to be at the end of an alkane
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