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FSE1105-Thanatochemistry-Chapter10.pptxOther Classes of Organic Compounds
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Carboxylic Acids
The carboxylic acids are also known as organic acids.
They are characterized by the presence of the carboxyl group (-COOH).
The carboxyl group is an end carbon to which a double bonded oxygen and a hydroxide group are attached.
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Carboxylic Acids
Organic acids have the general formula of R-COOH.
The “R” may be either a hydrogen in the simplest case or an alkyl group.
The carboxylic acids have the suffix “-OIC” with most common names ending in –“IC”.
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Carboxylic Acids
The rule for naming acids:
take the name of the corresponding alkane.
Drop the “-e” and add the ending “-oic” and add the word acid.
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Carboxylic Acids
The smallest of the organic acids is formic acid (methanoic acid).
Formic acid is the result of the oxidation of formaldehyde(methanal).
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Carboxylic Acids
The 2nd of the organic acids is acetic acid (ethanoic acid).
Ethanoic acid is produced from the oxidation of acetaldehyde (ethanal).
This is the type of acid found in vinegar.
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Ketones
The ketones are characterized by the presence of the carbonyl functional group located on an inside carbon of the chain.
The double bonded oxygen must be attached to an inside carbon of a chain of carbons.
There must be at least 3 carbons in the chain before you can have a ketone.
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Ketones
The ketones as a class have the general formula R-CO-R.
The “R”s must be alkyl groups.
They do not need to be the same alkyl group.
Ketones have the suffix of “-ONE”
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Ketones
The rule for naming ketones:
Take the name of the corresponding alkane.
Drop the “-e” and add “-one”.
The name for those with more than 4 carbons should be preceded by the address of the carbon with the double bonded oxygen using smallest numbers.
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Ketones
Ketones may also be named by the alkyl method:
First name the two alkyl groups on either side of the carbonyl group.
Do not count the carbon with the double bonded oxygen)
Add the word “ketone”.
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Ketones
The smallest of the ketones is propanone.
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Ketones
Propanone is also known as:
Acetone.
Dimethyl ketone.
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Esters
Esters are formed from the removal of water that occurs between an organic acid (carboxylic acid) and an alcohol.
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Esters
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Esters
They are characterized by the presence of a –COOC – functional group.
This is a double bonded oxygen attached to a carbon that is then attached to an oxygen which is then attached to another carbon.
I know it sounds confusing, but look at the picture.
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Esters
There are minimum of 2 carbons separated by an oxygen before you can have an ester.
Esters have the general formula R-COO-R.
The “R”s do not need to be the same. The first “R” may even be a hydrogen.
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Esters
Esters are named according to the parent compounds from which they are derived. The rules for naming an ester:
Take the name of the parent alcohol followed by a parent acid.
Drop the ending “-ic” from the acid name and add “-ate”.
The common names for these compounds are derived similarly but using the common name of the parent acid.
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Esters
The esters as a class of compounds all tend to have very pleasing odors.
Esters are found in some cavity fluids, sanitizing sprays, and sealing lacquers.
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Esters
Esters can cause eye irritation and also irritate mucous membranes.
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Esters
A common ester is methyl salicylate, known as oil of Wintergreen which is a common perfuming agent. Methyl salicylate is an aromatic ester.
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Ethers
Ethers are formed from the dehydration that occurs between two alcohols. The alcohols do not need to be the same.
There are characterized by the presence of oxygen in the carbon chain. The functional group looks like this: -C-O-C-.
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Ethers
There are minimum of 2 carbons separated by an oxygen before you can have an ether.
Ethers have the general formula R-O-R.
The “R”s do not have to be the same, they may be of different numbers of carbons.
Neither “R” may be only a hydrogen.
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Ethers
Ethers derived from the same parent alcohol are called simple ethers while those derived from 2 different alcohols are called mixed ethers.
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Ethers
The rule for naming ethers:
Name the two carbon chains (alkyl groups).
Add the word ‘ether’.
Some ethers are simply identified by the name of the parent alcohol. Instead of saying “diethyl ether” it is called “ethyl ether”.
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Ethers
Another way to name the ethers is to use the “aloxy method”.
Name the smallest alkyl group by its “aloxy” name such as “methoxy” or “ethoxy”.
Follow with the alkane name of the longest alkyl group.
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Ethers
One of the most common ethers is ethyl ether. Ethyl ether is used as an anesthetic and is a general purpose solvent.
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Ethers
Ethers are usually extremely flammable and can form explosive mixtures with air. One should never use an ether near a flame or spark which is why surgeons wear nonconductive shoes when in the operating room.
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Amines
The amines are derived from ammonia where a hydrogen has been replaced by an alkyl group.
Amines resemble an alkane that is had one of its hydrogens replaced by an amino group (-NH2).
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Amines
Amines are derivatives of ammonia and/or proteins in the body.
Amines are organic compounds characterized by the amino functional group. As a group this class of compounds are identified by the general formula R-NH2.
The “R” stands for the alkyl group.
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Amines
Amines have the suffix “-amine.”
The rules for naming this class of compounds are similar to naming alcohols in that the amino group is treated like a hydroxide and should be addressed if its position could be confused.
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Amines
Amines are important because they are associated with decomposition of proteins in the body. They are characterized by disagreeable odors and the fact that they form alkaline solutions because they are Lewis bases.
If you are really interested, you can look up Lewis compounds on your own.
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Amines
Some amines have 2 amino groups in their structure and are known as diamines.
The 2 most common diamines that are associated with decomposition of the human body are putrescine and cadaverine.
As you can imagine, these both quite literally stink. Bad.
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Amines
Amines are basic compounds and easily form salts.
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Quaternary Salts
Quaternary ammonium salts are formed from the action of tertiary amines with organic halides.
Some quarternary ammonium salts have both a detergent action and an antibacterial action.
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Quaternary Salts
They are used medicinally as antiseptics.
Benzalkonium Chloride (zephiran chloride) is used to store sterile instruments, as a wet dressing, or may be even used to irrigate the bladder and urethra.
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Amides
Amides may be derived from the dehydration of organic acids and ammonia (or an amine). Because this is a neutralization reaction, chemically they are ammonium salts.
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Amides
Amides are any group of compounds derived from ammonia by the substitution or replacement of a hydrogen by a carbonyl group (C=O).
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Amides
They may be derived from the acid by replacing the hydroxide (-OH) group with an amino group (-NH2).
The simplest of the amides as a class have the following general formula, R-CONH-R.
the 1st “R” stands for the alkyl group from the parent acid. The 2nd “R” is the alkyl group from the parent amine.
Amides have the suffix “-amide”.
R
R
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Amides
The rules for naming amides:
Name the alkyl group of the amine.
If the amide is derived from ammonia and not from an amine then omit this part of the name).
Take the name of the parent acid, drop the “-oic” and replace it with the amid suffix “-amide”.
Common names of the acid parent may be used as well; just drop the suffix “-ic” and add the “-amide”.
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Amides
Two of the more common amides found in the preparation room are dimethyl formamide and diethyl formamide and are solvents.
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Amides
Another amide of some significance to us as embalmers is urea.
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Amides
Urea is a diamide produced as a waste product from the metabolism of proteins in the body. Urea is the substance that must be removed by the kidneys to produce urine.
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Amides
If urea is not removed from the body a condition known as uremia occurs. This is problematic because urea will bond with formaldehyde and neutralize it.
We combat this generally by ensuring we use higher index fluids or higher concentration/volume to meet preservative demand.
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Mercaptans
Thioalcohols or mercaptans are very similar to the alcohols except that the oxygen in the hydroxyl group has been replaced by a sulfur.
They have the general molecular formula of R-SH.
Some of the common mercaptans are methyl mercaptan and ethyl mercaptan.
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Mercaptans
Methyl mercaptan is the odor of urine after the ingestion of asparagus.
This is probably why you can't find a methyl mercaptan scented Yankee candle.
Ethel mercaptan is the substance that is added to natural gas to give it a detectable odor.
Another popular seller at Yankee candle, I’m sure.
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Closing Notes
In closing this chapter, I offer you the following advice:
Write and rewrite the charts in the summary at the conclusion of chapter 10.
Draw linear guides of the oxidation reactions until you can do it from memory.
The reductions are simply the exact opposite. If you can draw oxidations from memory you should be able to work your way back using reductions.
Utilize online study sites such as Quizlet and Study Stack to assist you in memorization.
Making your own note cards for the general molecular formulas and general formulas is an absolute must.
Prefixes and suffixes also need to be note carded and memorized.
There is no substitution for spending the time and doing the work if you want to retain this for the long term.
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References:
The following Textbook References were used to create this presentation:
Funeral Service Chemistry by Professional Trade Schools
Embalming: Theory, History, and Practice by Robert G. Mayer (5th Edition).
Charts were taken from the textbook unless otherwise indicated
Pictures and art used in this presentation have the reference and location stored in the graphic. Please hover the mouse over the image to find where it was obtained.
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