Prentice Hall,Copyright 2007. 16.4 Some Common Aldehydes and Ketones Formaldehyde is a colorless gas. Low concentrations in air cause eye, throat, and.

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Prentice Hall,Copyright 2007

16.4 Some Common Aldehydes and Ketones Formaldehyde is a colorless gas. Low concentrations in air cause eye, throat, and bronchial irritation, and high concentrations trigger asthma attacks. Skin contact produces dermatitis. CH 2 O is very toxic by ingestion, causing serious kidney damage, coma, and sometimes even death. CH 2 O kills viruses, fungi, and bacteria by reaction with the groups in proteins, allowing for its use in disinfecting and sterilizing equipment and as a preservative for biological specimens.

Prentice Hall,Copyright 2007 The first successful synthetic plastic was a polymer of phenol and formaldehyde known as Bakelite, once widely used for such items as pot handles, fountain pens, and cameras. Urea–formaldehyde polymers are now more widely used than Bakelite. ►CH 2 O polymers release CH 2 O into the air. Concerns over the toxicity and possible carcinogenicity of CH 2 O limits most household applications.

Prentice Hall,Copyright 2007 Acetaldehyde is a sweet-smelling, flammable liquid present in ripe fruits, and produced in the normal breakdown of carbohydrates. Acetaldehyde is a general narcotic, and large doses can cause respiratory failure. Chronic exposure produces symptoms like those of alcoholism.

Prentice Hall,Copyright 2007 Acetone is one of the most widely used of all organic solvents. It dissolves most organic compounds and is also miscible with water. Acetone is the solvent in many varnishes, lacquers, and nail polish removers. When the metabolism of fats and carbohydrates is out of balance (for example, in starvation or diabetes mellitus), acetone is produced in the liver, a condition known as ketosis that in severe cases leaves the odor of acetone on a patient’s breath.

Prentice Hall,Copyright Oxidation of Aldehydes In aldehyde oxidation, the hydrogen bonded to the carbonyl carbon is replaced by an –OH group. Ketones, because they do not have this hydrogen, do not react with mild oxidizing agents.

Prentice Hall,Copyright 2007 (a) In the Tollens’ test, colorless silver ion is reduced to metallic silver. (b) In the Benedict’s test, the blue copper(II) ion is reduced to copper(I) in brick-red copper(I) oxide In both tests, the aldehyde is oxidized to the carboxylic acid. See text for picture of Tollen’s/benedicts tests in lab.