Hydrocarbon

derivatives-2
WEEK 3
ALDEHYDES
Note: Carbonyl is at the end of the chain.
Naming aliphatic aldehydes:
IUPAC System. (Aliphatic aldehydes)
Gen. formula: RCHO
Take the name of the longest chain containing the aldehyde group, drop the ending-e, and replace it with the
ending –al.
Note: The term aldehyde comes from the word dehydrogenation.
IUPAC System—(Aromatic aldehydes)
-Gen. Fromula: (ArCHO)
-Ar - stands for an aromatic ring
Benzaldehyde
-Simplest aromatic aldehyde
-Prepared by the mild oxidation of toluene.
Note: The side chain, the methyl group, is more susceptible to oxidation than the fairly stable benzene ring.
-Is a colorless, oily liquid with a cherry-almondlike odor.
-It is ude in the preparation of flavoring agents, perfumes, drugs and dyes.
Vanillin and Cinnamic Aldehyde (Cinnamaldehyde)
- Occurs in vanilla beans and gives the particular taste and odor to vanilla extract.
- Has an aldehyde structure.
-Both vanillin and cinnamic aldehyde can be prepared synthetically, and both are used as flavoring agents.
Uses of Aldehydes:
Formaldehyde
- It is a colorless gas with a very sharp odor.
- It is used in the laboratory as a water solution containing about 40% formaldehyde.
- The 40% solution commonly known as formalin is an effective germicide for the disinfection of excreta, rooms
and clothing.
- Formalin hardens protein, making it very insoluble in water.
- It is used as an embalming fluids and also as a preservative for biologic specimens.
- Formaldehyde solutions should not be used directly on a patient or even in the room with a patient because of
irritating fumes.
- Formaldehyde and its oxidation product, formic acid, are primarily responsible for the systemic toxicity of
mmethyl alcohol.
Glutaraldehyde
- Is superior to formaldehyde as a sterilizing agent and therefore is replacing it in use.
- Is microbial against all microorganisms, including spores and many viruses.
- Does not have the disagreeable odor that formaldehyde does, and it is less irritating to the eyes and skin.
Paraldehyde
- Is formed by the polymerization (joining) of three molecules of acetaldehyde.
- Depresses the central nervous system.
- It used as hypnotic, a sleep producer and is also used in the treatment of alcoholism.
- In therapeutic dosages it is nontoxic; it does not depress heart action or respiration.
- Its disadvantages are its disagreeable taste and unpleasant odor.
Acetaldehyde(Ethanal)
- Is responsible for many of the unpleasant side effects of ethyl alcohol consumption.
- The drug antabuse, used to treat alcoholics, functions by increasing the concentration of acetaldehyde in the
body.
Glyceraldehyde
-Is an important component in the metabolism of carbohydrates.
Test For Aldehydes
A) Test for glucose (sugar) in urine.
- Laboratory tests for the presence of aldehydes are based on the ability to reduce Copper 11(Cupric) ions to
form Copper 1(cuprous) oxide.
- When an aldehyde is heated with Benedict’s or Fehlin’s solution or treated with a Clini-test tablet(all of which
contain Cu2+ complex ion), a red precipitate of copper (1) oxide (Cu2O) is formed.
- Another laboratory tests for the presence of aldehyde involves the use of Tollen’s reagent, which contains an
Ag+ complex ion.
-In this test, the presence of an aldehyde causes the formation of a bright, shiny mirror on the inside of the test
tube, hence the name “Silver mirror test”.
Reactions of Aldehydes
- Oxidation- Aldehydes can be oxidized to form acids.
- Reduction – Aldehyde can be reduced to the corresponding primary alcohols.
- Biologic oxidation-reduction in the body is carried out by substances called coenzymes.
- One coenzyme, nicotinamide adenine dinucleotide (NAD+), acts as an oxidizing agent and in turn is
reduced to nicotinamide adenine dinucleotide hydride(NADH).
KETONES
Acetone (propanone) is the simplest ketone
Gen. Formula-RCOR
Note: Carbonyl group is at the middle of the chain.
Naming Aliphatic Ketones;
IUPAC System, take the name of the longest alkane containing the carbonyl group , drop the ending –e and
add one.
Common System, its alkyl group attached to the carbonyl is named and the word ketone is added afterward.
Aromatic ketones- Gen. Formula (ArCAr) or ArCOR)
- The simplest aromatic ketone is acetaphenone
Acetaphenone
-Used as a hypnotic but has been supplanted for this purpose by newer and safer drugs-chloracetaphenone , is
a ;lacrimator and is used as an tear gas.
- Among the aromatic ketones in the body are the sex hormones; estrone, progesterone, testosterone, and
androsterone.
Uses of Ketones
Acetone
- It is good solvent for fats and oils.
- It is also frequently used in fingernail polish and in polish remover.
- Is normally present in small amounts in the blood and urine.
- In diabetes mellitus, It is present in larger amounts in the blood and urine and even in the expired air.
Dihydroxyacetone
- It is intermediate in carbohydrate metabolism.
Reactions of Ketones
- Ketones are not easily oxidized.
- They are normally unreacted-Ketones can be reduced however to the corresponding secondary alcohol.
- Ketones give a negative test with such oxidizing agents as Benedict’s solution or clini-test tablets.-While
aldehydes give a positive test with this reagents.
- The test for acetone and ketone bodies makes use of the reaction between sodium nitroprusside and ketones or
ketone bodies to make a lavender color.
Hemiacetals and Hemiketals
- The reaction of an aldehyde or a ketone with an alcohol yields compounds known as “hemiacetals or
hemiketals” respectively.
- If the hemiacetal and hemiketal reacts with a second molecule of alcohol, an “acetal or ketal”, respectively is
formed.
- These structures are important in disaccharide and polysaccharides.
ORGANIC ACIDS Preparation by oxidation of an aldehyde
- IUPAC system;
Take the longest chain containing the acid group, drop the ending -e and add-oic acid.
- Common system;
- Derived from the names of the aldehyde from they may be prepared.
- Gen. Formula- RCOOH or ArCOOH
- All organic acids containing two carboxyl groups are called dicarboxylic acids.
Properties and reaction of Organic Acids:
- Most organic acids are relatively weak acids since they ionize only slightly in water.
- Organic acids also react with bicarbonates and carbonates.
- Organic acids containing few carbon atoms are soluble in water. As the length of carbon chain increases, the
solubility in water decreases.
- Organic acids also react with alcohols to form a class of compounds called esters.
Medically Important Organic Acids
Formic acid (HCOOH)
- It is colorless liquid with a sharp, irritating odor.
- Found in the sting of bees and ants and causes the characteristic pain and swelling when it is injected into the
tissues.

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-It is one of the strongest organic acids.
Acetic acid (CH3COOH)
- Is one of the components of vinegar, where it is usually found as a 4 to 5 percent solution.
- Can be made by the oxidation of ethyl alcohol.
- The acetyl group derived from acetic acid , is very important in metabolic reactions.
Citric Acid
- Found in the citrus fruits
- Contains one alcohol (---COOH acid group
- It is an example of tricarboxylic acid
- Magnesium citrate – a salt of citric acid ( a medication for stimulating the evacuation of the bowels).
- Sodium citrate- another salt of citric acid, is used as blood anticoagulant . (It removes Ca2+ needed for
coagulation from the blood).
Lactic acid
- Is found in sour milk
- It is formed in the fermentation of milk sugar, lactose
- Lactic acid is also both an acid and an alcohol.
- It is formed whenever the body produces energy anaerobically.
Oxalic acid
-Is another one of the strong, naturally occurring organic acids.
It is used to remove strains, particularly rust and potassium permanganate stains, from clothing
- It is poisonous when take internally.
- Oxalate salts also prevent clotting by “chelating Ca2+ from the blood.
- However, oxalate can be used only for blood samples that are to be analyzed in the laboratory.
- Because these salts are poisonous and cannot be added directly to the bloodstream.
Pyruvic acid
- Is produce during the anaerobic phase of oxidation of glucose.
- It is a keto acid
- In muscle, pyruvic acid is reduced to lactic acid during anaerobic exercise.
- In the tissues, pyruvic acid is changed to acetyl coenzyme A, which then enter the Krebs cycle.
Tartaric Acid
- Is another organic acid.
- That is both acid and an alcohol.
- Found in several foods particularly grapes.
- Potassium hydrogen tartrate-an acid salt called cream of tartar, is used in making baking powder. Rochelle salts,
or potassium sodium tartrate, is used as mild cathartic.
Stearic acid- (C17H35COOH
- Is a solid greaselike acid that is insoluble in water.
- It is an example of fatty acid.
- The sodium salt of stearic acid, sodium stearate, is a commonly used soap.
Benzoic acid
- Can be produced by the oxidation of benzaldehyde or by the oxidation of toluene.
- Is a white crystalline compound that is slightly soluble in cold and more soluble in hot water.
- It is used medically as an antifungal agent.
- The sodium salt of benzoic acid, sodium benzoate, is used as preservative.
Salicylic acid
- Is both an alcohol and an acid.
- Is white crystalline compound with properties also for removal of warts and corns.
- Commonly used compounds of salicylic acid are the salt sodium salicylate and the ester methyl salicylate.
- Sodium salicylate – is used as an antipyretic (to reduce fever) and also to relieve pain for arthritis, bursitis and
headache.

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Definition of Bursitis

* inflammation of a bursa, typically one in the knee, elbow or shoulder.

- Methyl salycilate- is a liquid with a pleasant odor , that of wintergreen. It is used topically to relieve pain in
muscles and joints.
- Acetyl salicylic acid (Aspirin) –acetyl derivative of salicylic acid (the acetyl group-CH3CO.
- Used as an analgesic, as an antipyretic; for the treatment of colds, headaches, minor aches and pains; and as a
mild thinner , especially of individuals who have had a coronary artery bypass.
- Used in the treatment of Rheumatic fever.
- Contraindicated after surgery because it interferes with normal blood clotting and can induce hemorrhaging.
Aspirin can also cause bleeding of the stomach and therefore should not be taken in an empty stomach. The
action of aspirin is related directly to that of the prostaglandins. Aspirin stimulates respiration directly and
overdoses can cause serious acid-base balance disturbances. Evidences appears to indicate that aspirin can
prevent blood clots from forming by interfering the action of the blood platelets. There s also evidence that
one aspirin every other day helps prevent heart attacks.
- Acetaminophen (Tylenol) – has been used as substitute for aspirin because it does cause gastrointestinal
bleeding and does not affect blood clotting. However, overdoses can lead to hepatic damage, as can be the
case with aspirin itself. It is not effective itself. It is not effective against inflammation.
Coronary
Artery
By-pass
Graft
MORE EXAMPLES
The Glucose Molecule