The Amazing World of Alcohol 2
The term Alcohol, refers to any of a class of organic compounds characterized by one or more hydroxyl (―OH) groups attached to a carbon atom of an alkyl group (hydrocarbon chain).
Alcohols may be considered as organic derivatives of water (H2O) in which one of the hydrogen atoms has been replaced by an alkyl group, typically represented by R in organic structures. For example, in ethanol (or ethyl alcohol) the alkyl group is the ethyl group, ―CH2CH3.
Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Perhaps the two best-known alcohols are ethanol and methanol (or methyl alcohol). Ethanol is used in toiletries, pharmaceuticals, and fuels, and it is used to sterilize hospital instruments. It is, moreover, the alcohol in alcoholic beverages. The anesthetic ether is also made from ethanol. Methanol is used as a solvent, as a raw material for the manufacture of formaldehyde and special resins, in special fuels, in antifreeze, and for cleaning metals.
Classifications
Alcohols may be classified as primary, secondary, or tertiary, according to which carbon of the alkyl group is bonded to the hydroxyl group. Most alcohols are colorless liquids or solids at room temperature. Alcohols of low molecular weight are highly soluble in water; with increasing molecular weight, they become less soluble in water, and their boiling points, vapor pressures, densities, and viscosities increase.
Another way of classifying alcohols is based on which carbon atom is bonded to the hydroxyl group. If this carbon is primary (1°, bonded to only one other carbon atom), the compound is a primary alcohol. A secondary alcohol has the hydroxyl group on a secondary (2°) carbon atom, which is bonded to two other carbon atoms. Similarly, a tertiary alcohol has the hydroxyl group on a tertiary (3°) carbon atom, which is bonded to three other carbons. Alcohols are referred to as allylic or benzylic if the hydroxyl group is bonded to an allylic carbon atom (adjacent to a C=C double bond) or a benzylic carbon atom (next to a benzene ring), respectively.
Nomenclature
As with other types of organic compounds, alcohols are named by both formal and common systems. The most generally applicable system was adopted at a meeting of the International Union of Pure and Applied Chemistry (IUPAC) in Paris in 1957. Using the IUPAC system, the name for an alcohol uses the -ol suffix with the name of the parent alkane, together with a number to give the location of the hydroxyl group. The rules are summarized in a three-step procedure:
- Name the longest carbon chain that contains the carbon atom bearing the ―OH group. Drop the final -e from the alkane name, and add the suffix -ol.
- Number the longest carbon chain starting at the end nearest the ―OH group, and use the appropriate number, if necessary, to indicate the position of the ―OH group.
- Name the substituents, and give their numbers as for an alkane or alkene.
The example on the right has a longest chain of six carbon atoms, so the root name is hexanol. The ―OH group is on the third carbon atom, which is indicated by the name 3-hexanol. There is a methyl group on carbon 3 and a chlorine atom on carbon 2. The complete IUPAC name is 2-chloro-3-methyl-3-hexanol. The prefix cyclo- is used for alcohols with cyclic alkyl groups. The hydroxyl group is assumed to be on carbon 1, and the ring is numbered in the direction to give the lowest possible numbers to the other substituents, as in, for example, 2,2-dimethylcyclopentanol.
Common Names
The common name of an alcohol combines the name of the alkyl group with the word alcohol. If the alkyl group is complex, the common name becomes awkward and the IUPAC name should be used. Common names often incorporate obsolete terms in the naming of the alkyl group; for example, amyl is frequently used instead of pentyl for a five-carbon chain.
Physical Properties
Most of the common alcohols are colorless liquids at room temperature. Methyl alcohol, ethyl alcohol, and isopropyl alcohol are free-flowing liquids with fruity aromas. The higher alcohols—those containing 4 to 10 carbon atoms—are somewhat viscous, or oily, and they have heavier fruity odors. Some of the highly branched alcohols and many alcohols containing more than 12 carbon atoms are solids at room temperature.
Featured Alcohol: Octanol
1-Octanol, also known as octan-1-ol, is the organic compound with the molecular formula CH3(CH2)7OH. It is a fatty alcohol. Many other isomers are also known generically as octanols.
1-Octanol is commonly manufactured for the synthesis of esters for use in perfumes and flavorings. It has a pungent odor. Esters of octanol, such as octyl acetate, occur as components of essential oils. 1-Octanol is also used to evaluate the lipophilicity of pharmaceutical products.
Octanol is mainly produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products. This route is known as the Ziegler alcohol synthesis.The process generates a range of alcohols, which can be separated by distillation.
The Kuraray process defines an alternative route to 1-octanol, but using C4 + C4 building strategy. 1,3-Butadiene is dimerized concomitant with the addition of one molecule of water. This conversion is catalyzed by palladium complexes. The resulting doubly unsaturated alcohol is then hydrogenated.
Octanol and water are immiscible. The distribution of a compound between water and octanol is used to calculate the partition coefficient, P, of that molecule (often expressed as its logarithm to the base 10, log P). Water/octanol partitioning is a relatively good approximation of the partitioning between the cytosol and lipid membranes of living systems.
Toxicity
After inhalation: fresh air.
In case of skin contact: Take off immediately all contaminated clothing. Rinse skin with water/ shower.
After eye contact: rinse out with plenty of water. Call in ophthalmologist. Remove contact lenses.
Aroma
- Octanol is often described as having an aroma of orange and rose.
- Octanal is often described as having a citrus, fatty aroma.
- Octanoic Acid is often described as having a waxy and creamy smell.
- Octyl acetate (the ester formed with ethanol) has a scent of jasmine.