Classes of Organic Compounds Flashcards
ALDEHYDES
An aldehyde is defined as an organic compound containing one or more (-CHO) groups.
functional group: CHO
general formula: R-CHO
The name aldehyde comes from alcohol deprived of hydrogen, which is one of the ways aldehydes are formed.
You can partially oxidize a primary alcohol to get an aldehyde.
NAMING AN ALDEHYDE
To name an aldehyde replace the (E) ending of the saturated hydrocarbon with (AL); just as (OL) was used for alcohols.
Methane → Methanol → Methanal
- An aldehydes’ other name is derived from the prefix of its corresponding organic acids’ source.
So, you must count the carbon within the functional group when you are naming an aldehyde.
MONOALDEHYDES
Monoaldehydes are aldehydes that contain one CHO group. Ex. METHANAL / FORMALDEHYDE Molecular formula is: CH2O Line Formula is: HCHO
METHANAL / FORMALDEHYDE
Molecular formula is: CH2O
Line Formula is: HCHO
Ethanal is prepared by the partial oxidation of Methyl alcohol / Methanol.
PROPERTIES OF METHANAL / FORMALDEHYDE:
Formaldehyde is a colorless gas with an irritating / suffocating odor.
Formaldehyde is soluble in water.
Formaldehyde is readily oxidized to formic acid / methanoic acid.
It reacts with ammonia to form UROTROPIN / Methenamine (C6H12N4). Urotropine is the neutralization product of formaldehyde by ammonia.
The formation of Urotropin demonstrates the affinity of formaldehyde for nitrogen. ANY compound that contains nitrogen will attract formaldehyde. The end result is the “Neutralization” of formaldehyde.
UROTROPIN
Formaldehyde reacts with ammonia to form UROTROPIN / Methenamine (C6H12N4). Urotropine is the neutralization product of formaldehyde by ammonia.
The formation of Urotropin demonstrates the affinity of formaldehyde for nitrogen. ANY compound that contains nitrogen will attract formaldehyde. The end result is the “Neutralization” of formaldehyde.
Formaldehyde + Ammonia → UROTROPIN (Methenamine) + Water
6 HCHO + 4NH3 → C6H12N4 + 6 H2O
POLYMERIZATION
the linking together of monomers (basic chemical units) to form a polymer which is a large molecule that is a multiple of the original weight molecule.
polymerization is the process or the tendency of a molecule to combine with itself resulting in a product called a polymer
polymerization is the reaction between molecules of the same kind.
Polymerization of Formaldehyde
Formaldehyde has the tendency to polymerize to paraform / paraformaldehyde.
In the case of formaldehyde you start out with a liquid and end up with a powder which is no longer formaldehyde, it is now PARAFORM / PARAFORMALDEHYDE which precipitates out of solution because it is now a much larger molecule.
Paraform is undesirable in arterial fluids; it is used as the major preservative in solid autopsy compounds.
Methyl Alcohol is routinely included in the composition of arterial embalming fluids as an anti-polymerizing agent for formaldehyde.
USES OF FORMALDEHYDE
Formaldehyde is a good disinfectant on inanimate objects.
It is a good preservative - it reacts with proteins and preserves them. This is what we do as embalmers – preserve the body’s protein.
It is a great reducing agent.
It acts as a bactericide (kills bacteria) and inhibits yeast and mold growth.
FORMALIN
A saturated solution of formaldehyde, water and another agent, most commonly methanol. The dissolved formaldehyde gas is at a specific percentage. A solution of formalin is:
37% formaldehyde by weight
or
40% formaldehyde by volume,
6-15% methanol,
&
the rest is water
It’s the addition of methyl alcohol (methanol) that causes the substance to be called formalin as opposed to formaldehyde.
INDEX
a term used by embalmers to express the concentration of formaldehyde in embalming fluid.
Index is a term used to indicate the strength of embalming fluid.
Index is defined as the number of grams of pure formaldehyde gas in 100 milliliters of solution.
INDEX OF ARTERIAL FLUID
5 - 15 = LOW INDEX
16 - 25 = MEDIUM INDEX
26 - 36 = HIGH INDEX
ETHANAL / ACETALDEHYDE:
Ethanal / Acetaldehyde is a monoaldehyde.
Molecular formula is: C2H4O
Line Formula is: CH3CHO
Structural formula is:
ethanal / acetaldehyde
PARALDEHYDE
PARALDEHYDE is the polymer of ethanal / acetaldehyde. When you polymerize ethanal you get paraldehyde.
There are two ways to get ETHANAL:
- When you partially oxidize ethanol you get ethanal.
- When you reduce ethanoic acid you get ethanal.
DIALDEHYDES
Dialdehydes are those aldehydes that contain two (2) CHO groups.
GLYOXAL
GLYOXAL
Molecular formula is: C2H2O2
Line Formula is: (CHO)2
Glyoxal is the simplest dialdehyde.
As you can see it is simply two CHO groups.
Glyoxal is 75% effective in embalming; however it tends to stain tissue yellow so when it is used in embalming it produces a yellow color to the deceased. For this reason, the use of glyoxal is limited to cavity fluid.
GLUTARALDEHYDE:
Molecular formula is: C5H8O2
Line Formula is: OCH(CH2)3CHO
- Glutaraldehyde is an excellent germicide that has outstanding disinfectant qualities, known as a “cold chemical sterilant”.
- -Glutaraldehyde is a good preservative that produces less firming than formaldehyde. Some embalmers prefer this because they feel it gives a more “life-like” appearance to the deceased.
- Glutaraldehyde works over a wide pH range.
- It’s a colorless water soluble liquid agent with a sharp mint like odor.
pH
pH is the measure of hydrogen ion (H+) concentration of a solution. Acids have a pH below 7, bases have a pH above 7, and neutral substances have a pH equal to 7.
Glutaraldehyde Demand
The amount of glutaraldehyde necessary to overcome any nitrogen residue and cause the body proteins to be coagulated thus resulting in preservation.
CYCLIC /AROMATIC ALDEHYDES
Aromatic compounds contain carbon atoms arranged in a ring-like pattern.
Aromatic aldehydes are used as reodorants / perfuming agents in embalming fluids.
Reodorant
Reodorants differ from deodorants in that they only replace the odor, they do not decompose it like deodorants do.
BENZALDEHYDE
Molecular formula is: C7H6O
Line Formula is: C6H5CHO
Benzaldehyde is the simplest of aromatic aldehydes. It is simply the benzene ring with a CHO group attached.
It is a colorless oily liquid, which smells like almonds.
Benzaldehyde is used as a perfuming and flavoring agent. ex. imitation almond extract
KETONES
- A ketone is defined as any class of organic compounds contained the carbonyl group (C=O), whose carbon atom is joined to two other carbon atoms. The carbon atom occurs within the carbon chain (not at the end of the carbon chain).
- Ketones are derivatives of the hydrocarbons.
- The functional group of ketones is CO –, the carbonyl group.
- A carbonyl group is a chemical group composed of one carbon atom double bonded to oxygen.
- The general formula for a ketone is R-CO-R (where both R’s do not have to be the same).
- Ketones are prepared by the partial oxidation of secondary alcohols.
NAMING KETONES two (2) ways
- The first way to name a ketone is to:
Name the compound according to the radicals (R) or alkyl groups that are attached to the functional group.
First you “read” the line formula from left to right naming the radicals accordingly; (you need to know your radicals to do this), and then add the word ketone.
If both radicals are the same use the prefix di.
For Example:
CH3COCH3 - Dimethyl Ketone
The second way to name a ketone is to:
Count the number of carbon atoms in the compound and change the -E ending of the originating saturated hydrocarbon to -ONE.
All of the carbons in the compound are counted including the one in the functional group.
For Example:
Propane → Propanone - CH3COCH3
ACETONE / DIMETHYL KETONE / PROPANONE
Molecular formula is: C3H6O
Line Formula is: CH3COCH3
Propanone is the simplest ketone since it is made up of the simplest radicals (methyl) and the functional group.
Propanone is formed by the oxidation of isopropyl alcohol (a secondary alcohol).
PROPERTIES of ACETONE
It is colorless.
It is soluble in water.
It is the active ingredient in nail polish remover, however it also removes adhesives.
It is a good solvent for lacquers.
It has a funny sweet odor which can be given to the breath and urine of a diabetic during a state called Diabetic Keto-acidosis (DKA) or Acidosis. This state can occur when there is an accumulation of Dimethyl Ketone in the body which can develop due to an abnormally high blood sugar.
ORGANIC ACIDS / CARBOXYLIC ACIDS
Organic acids were once a hydrocarbon that lost one hydrogen atom which was then replaced with the functional group –COOH.
Organic acids are also known as carboxylic acids due to their functional group being the carboxyl group.
The carboxyl group (COOH) is made up of the (CO) carbonyl and (OH) hydroxyl groups, which is how it got its name.
The general formula is R-COOH and the functional group is COOH for organic acids.
Organic acids can be prepared in two ways
- By partially oxidizing an aldehyde → organic acid
structural formula for formaldehyde
formic acid
—————————->
Formaldehyde Methanal
Formic acid Methanoic acid
- By fully oxidizing a primary alcohol → organic acid
ethanol
acetic acid
—————————>
Ethanol Ethyl alcohol Grain Alcohol
Acetic acid Ethanoic acid
As you can see from the first example (Methanoic Acid) you only need a hydrogen atom as the (R)/alkyl group since the functional group already contains a carbon
atom and notice only one (R)/alkyl group is needed because the general formula is R-COOH.
NAMING CARBOXYLIC ACIDS
here are two ways to name an organic acid:
- Change the -E ending of the originating hydrocarbon to -OIC and then add the word acid.
Methane → Methanoic Acid - HCOOH - Name the organic acid utilizing the common name that refers to their source rather than their chemical structure. (We are only responsible for the first two.)
Systematic Name
Common Name
Latin or Greek Origin
Methanoic Acid = Formic Acid = L. formica - “ant”
METHANOIC ACID / FORMIC ACID
Methanoic acid has only one carbon in its structure so the prefix meth- is used
the radical is simply one hydrogen atom and therefore it is the simplest of the organic acids.
Methanoic acid’s common name is formic acid because formica is Latin for ant, therefore an ant is its SOURCE.
Methanoic acid or formic acid is secreted in the stings or bites of ants and bees, in pine needles and nettle.
Methanoic acid is the strongest acid in the fatty acid series.
Fatty Acid
a monocarboxylic organic acid; an organic acid that contains only one carboxyl group (COOH). There is only one (1) COOH attached to the radical in the compound. They are called fatty acids because many of them occur in fats / lipids.
A fatty acid is an aliphatic compound which may be saturated or unsaturated. (Remember: saturated compounds contain single bonds while unsaturated compounds contain at least one double or triple bond).
ETHANOIC ACID / ACETIC ACID
Molecular formula is: C2H4O2
Line Formula is: CH3COOH
Acetic acid is the common name for ethanoic acid because acetum is Latin for vinegar which is its source…The vinegar you put on your salad is a 3-6% dilute solution of ethanoic / acetic acid. 100% Acetic Acid is called GLACIAL ACID because it forms crystals like a glacier when it is frozen.
ESTERS
An ester is defined as a substance formed from an alcohol and organic (carboxylic) acid by the removal of water.
The General Formula of an ester is R-COO-R.
The Functional Group of an ester is COO.
The suffix for esters is -ate.
Esters are the characteristic constituents of fruits and flowers, and they all have a pleasant odor.
Esters are produced by
…the interaction of organic acids + an alcohol.
organic acids + alcohol → ester + water
(acid) + (base) → (salt) + water
esterification
The equation used when discussing alcohols.
organic acids + alcohol → ester + water
(acid) + (base) → (salt) + water
It is an organic neutralization reaction, however because an ester is produced it can further be called an esterification reaction.
Due to the fact that an ester is produced via a neutralization reaction, we can say that an ester is an organic salt.
ETHYL ACETATE
Molecular formula is: C4H8O2
Line Formula is: C2H5COOCH3 or CH3CH2OC(O)CH3
Ethyl acetate is produced by the interaction of ethyl alcohol and acetic acid.
Ethyl Alcohol + Acetic Acid → Ethyl Acetate + Water
METHYL SALICYLATE / OIL OF WINTERGREEN
Molecular formula is: C8H8O3
Line Formula is: C6H4(OH)COOCH3
Methyl salicylate is produced by the interaction of salicylic acid and methyl alcohol.
Salicylic Acid + Methyl Alcohol → Methyl Salicylate + Water
Methyl salicylate is the principal ester used in embalming as a reodorant / masking agent (which only mask odors), they do not react with them to neutralize the odor. is a natural product of many species of plants.
Some of the plants producing it are called wintergreens, hence name oil of wintergreen.
ETHERS
The general formula for an ether is R-O-R.
The functional group for an ether is O.
Ethers are composed of two hydrocarbon radicals joined by an atom of oxygen, (the functional group is the oxygen atom), they are known as organic oxides.
To name an ether simply name the radicals (as you did with ketones) then add the word ether.
Ethers are prepared from alcohols: Alcohol + Alcohol → Ether + Water OH + OH → O + HOH OH + OH → O + HOH R-OH + HO-R → R-O-R Ethers are insoluble in water.
They are used as solvents for organic compounds and are extremely flammable.
METHYL ETHER / DIMETHYL ETHER
Molecular formula is: C2H6O
Line Formula is: CH3OCH3
It is two methyl radicals connected by an atom of oxygen, therefore the name dimethyl ether or simply methyl ether.
Dimethyl ether is used as an aerosol spray propellant, and in conjunction with propane is used to create a chemical reaction in which cryogenic freezing is used to remove common warts.
Dimethyl ether is also a clean-burning alternative to liquefied petroleum gas liquefied natural gas, diesel and gasoline.
BIS(CHLOROMETHYL) ETHER (BCME)
Molecular formula is : (CH2CI)2O
A carcinogen potentially produced when formaldehyde and Sodium Hypochlorite (bleach) come into contact with each other. It normally occurs only in a controlled laboratory setting and requires a catalyst.
BCME is a colorless liquid with a suffocating odor.
AMINES
The General Formula of an amine is R-NH2.
The Functional Group of an amine is NH2.
Amines are organic derivatives of ammonia in which 1 or more of the 3 hydrogen’s of NH3 are replaced by an alkyl (R) or aromatic (Ar) group(s).
Amines are the organic equivalent of a base, unlike alcohols which only act as a base.
Amines have very strong basic or alkaline qualities, and when they are put in water they act as a base; which is another way of saying “alkaline in solution”.
Because amines act as bases they have a tendency to neutralize acids; they react with acids in solution to form ammonium salts.
They have a very disagreeable odor, a strong fishlike odor
Ptomaines
Proteins are polymers of amino acids; (Remember, polymerization is the linking of monomers, basic chemical units, to form a polymer (a long chain of repeating units).
Amines and carboxylic acids are the constituents of amino acids, therefore amines are extremely important to us as embalmers because when protein decomposes amines are produced.
Amines are produced as the decomposition product of proteins (nitrogen based compound).
Since amines are the most important product of putrefaction (defined as the decomposition of proteins by the action of enzymes from anaerobic bacteria), in embalming terminology amines are known as:
Intermediate Products of Decomposition
or
Ptomaines (ptoma in Greek = corpse)
METHYL AMINE
Molecular formula is: CH5N
Line Formula is: CH3NH2
Methyl amine is the simplest amine.
PRIMARY AMINE
Skeleton Structure
Example: Methyl Amine
SECONDARY ANIME
Skeleton Structure
Example: Dimethyl Amine
TERTIARY ANIME
Skeleton Structure
Trimethyl amine
SALT (QUAT)
On a tertiary amine, when the two paired electrons are replaced with an alkyl halide you get a QUATERNARY AMMONIUM COMPOUND / SALT (QUAT).
When a tertiary amine reacts with an alkyl halide → QUAT
QUATS are incorporated as supplementary germicides in embalming fluids.
QUATS are used chiefly for their germicidal and deodorizing value.
The QUATS are not compatible with wetting agents and coloring material used in arterial fluids so they are restricted to DISINFECTING THE (NASAL & ORAL) CAVITIES and SKIN.
They are commonly found in cold sterilization formulations for instruments and other items; cleaning agents for mold proofing remains; and deodorant sprays. EXAMPLES include: Zephiran chloride, Roccal, Zepheral, Germitol, and Benzalkonium chloride.
Amides Creation
There is a name for those ammonium salts, it is amides.
Acid + Base → Salt + Water
Carboxylic Acid + Amine → Amide/Ammonium salt + Water
When an Amine reacts with a Carboxylic Acid the products formed are: Water + Amide / Ammonium Salt.
Amines have a tendency to neutralize acids; they react with acids in solution to form ammonium salts.
AMIDES
The general formula for amides is R-CONH-R′
The functional group for amides is CONH.
Notice on the second R the ′ which is called a prime. It means that the two radicals cannot be the same. R and R’ are variables, just like X is in Algebra, and can represent any bonded atom or groups of atoms.
In organic compounds, R and R’ can be just one single Hydrogen atom, or any organic group.
An example of the formation of an amide is:
Formic Acid
+
Methyl Amine
→
Methyl formamide
+
Water
(acid) (amine) (amide / ammonium salt) (water)
Amides are named in a similar manner to organic salts. The suffix amide replaces the ic name ending of the acids in the same way that the suffix ate did when organic salts (esters) were formed.
UREA
Molecular formula is:CH4N2O
Line formula is: (NH2)2CO
Urea is an amide and waste product of human protein.
It is formed in the liver from the breakdown of ammonia and secreted into the blood.
It is then selectively absorbed by the kidneys and excreted into the urine.
MERCAPTANS / THIOALCOHOLS / THIOLS
The General Formula for thiols is R-SH
The Functional Group is SH (Sulfhydryl Group).
Mercaptans, also known as thioalcohols or thiols, are sulfur analogs of alcohol which mean they contain SH instead of OH as their functional group. (Analogs are compounds with similar structures that differ from one another because of a certain component).
Mercaptans present as the final products of decomposition.
The proteins in the body are rich in SH (Sulfhydryl Groups), and because of the presence of sulfur they produce obnoxious smells which contribute to the odor of decomposition.
skunk odor is a mercaptan.
Asparagus is high in mercaptans
