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Oxygen-containing Compounds
Oxygen-containing compounds include alcohols, aldehydes, ketones, ethers, and carboxylic acids and derivatives. Thermo Fisher Scientific offers a range of oxygen-containing compounds and derivatives suitable for various research applications.
Alcohols are organic compounds that contain a hydroxyl group (-OH) attached to a carbon atom. Compounds containing hydroxyl groups have a wide range of laboratory applications in almost every field of chemistry and biology. They are used as synthetic intermediates and starting materials in an enormous number of organic reactions.
Ethers are a class of organic compounds that has an oxygen atom interposed between two alkyl or two aryl fragments, or between an alkyl and an aryl fragment. The simple or symmetrical ethers are those which have identical organic fragments attached to an oxygen atom (e.g., diethyl ether, dimethyl ether). The mixed or asymmetrical ethers are ones which have the different organic fragments attached to an oxygen atom (e.g., methyl ethyl ether, cyclopentyl methyl ether). The oxygen atom in ethers is more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. Ethers are classified as simple or symmetrical, or mixed or asymmetrical based on the organic fragments (R and R') attached to the oxygen atom.
Polyols are organic compounds containing multiple hydroxyl groups. Sugar alcohols such as maltitol, sorbitol, xylitol, and erythritol are examples of low molecular weight polyols; polyethylene glycol (PEG) and polypropylene glycol (PPG) are examples of polymeric polyols.
Phenols are organic compounds with a hydroxyl group directly attached to an aromatic carbon atom. Depending on the number of phenolic units in the molecule, they are classified as simple phenols and polyphenols. Phenols are efficient partners in a variety of reactions such as electrophilic aromatic substitutions, Bucherer carbazole synthesis, and oxidative de-aromatization to quinones in the Teuber reaction.
Polyphenols are naturally occurring organic compounds that contain multiple phenol units.. Examples of polyphenols are flavonoids, tannic acid, and ellagitannin, some of which have been used as dyes and tanning agents. Studies have shown polyphenols to be powerful antioxidants. Considered micronutrients that are widely found in plants, including foods such as fruits, vegetables, teas and spices, polyphenols are today also included in many supplements.
Aldehydes are a class of organic compounds which contain a formyl group, represented by -C(=O)H. Most of the aldehydes are colorless or pale-colored liquids with noticeable odors. The aldehydes, containing α-hydrogen, can exist as either a keto or enol tautomer, in which the enol tautomer is more reactive. Aldehydes generally undergo addition reactions by losing a water molecule, known as an addition-elimination or condensation reaction. Cyanohydrins, formed through this mechanism, are a route to the synthesis of important α-hydroxy acids. Aldehydes are efficient partners in the Wittig reaction for the synthesis of olefins. They are also important intermediates in organic synthesis for the preparation of alcohols, imines, and amines.
Ketones are a class of organic compounds that contain a carbonyl group bonded to two other organic fragments through carbon [R(C=O)R'], where R and R’ can be an alkyl or an aryl group. Ketones are either pleasant-smelling liquids or odorless solids. Examples of ketones are acetophenone, acetone, butanone, propanone, cyclohexanone, and cyclopentanone. They are widely present in nature (e.g., camphor, carvone, progesterone, cortisone, etc). Ketones with the α-hydrogen atom in acidic or basic conditions undergo keto-enol tautomerization. The keto form is more stable than the enol form.
Ketones have various uses in chemistry, medicine, and industry. In organic synthesis, ketones are employed in various reversible addition reactions such as the formation of hemiacetals, acetals, imines, enamines, and cyanohydrins; and irreversible addition reactions such as reduction by complex metal hydrides and addition of organometallic reagents. Ketones undergo reactions such as Wolff-Kishner reduction and Clemmensen reduction which result in the formation of corresponding alkanes. They are also useful as protecting agents to protect diols in organic synthesis.
Carboxylic acids are Brønsted-Lowry acids. They are highly polar organic compounds, their polarity resulting from the presence of a strongly polarized carbonyl (C=O) group and a hydroxyl (O-H) group. The dipoles present in carboxylic acids allow these compounds to participate in energetically favorable hydrogen bonding, hence their tendency to form a dimeric pair in non-polar media. There are wide ranges of carboxylic acid derivatives, which include esters, amides, acid chlorides, anhydrides, and imides.
Carboxylic acids and their derivatives play a vital role in research in drug discovery, biology, materials, and diagnostics.
The characteristic structure of peroxy compounds is the relatively weak oxygen-oxygen linkage. The weak -O-O- bond is easily split into reactive radicals via homolytic cleavage. As the active oxygen content and oxygen balance increase, the sensitivity and instability of peroxy compounds increase. Organic peroxy compounds fall in two categories, namely peroxy acids and organic peroxides. Examples of organic peroxides are t-butylhydroperoxide and dibenzoyl peroxide. Peroxy compounds find use in mouthwash, disinfectants, bleaching, rubber, and detection devices.
Synthesis of peroxy compounds generally involves hydrogen peroxide. In polymerization and addition reactions, the peroxy compounds are used as a source of free radicals. Dibenzoyl peroxide is a well-known radical initiator. Several polymers such as polyethylene (plastics) and polycaprolactam (nylon) are manufactured with peroxy compounds. Organic peroxides, through radical polymerization, play a key role in the manufacture of acrylic and methacrylic polymers.
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