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20.13 Properties and Uses of Alcohols

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    Alcohols

    Incorporation of an oxygen atom into carbon- and hydrogen-containing molecules leads to new functional groups and new families of compounds. When the oxygen atom is attached by single bonds, the molecule is either an alcohol or ether.

    Alcohols are derivatives of hydrocarbons in which an –OH group has replaced a hydrogen atom. Although all alcohols have one or more hydroxyl (–OH) functional groups, they do not behave like bases such as NaOH and KOH. NaOH and KOH are ionic compounds that contain OH– ions. Alcohols are covalent molecules; the –OH group in an alcohol molecule is attached to a carbon atom by a covalent bond.

    Ethanol, CH3CH2OH, also called ethyl alcohol, is a particularly important alcohol for human use. Ethanol is the alcohol produced by some species of yeast that is found in wine, beer, and distilled drinks. It has long been prepared by humans harnessing the metabolic efforts of yeasts in fermenting various sugars:

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    Large quantities of ethanol are synthesized from the addition reaction of water with ethylene using an acid as a catalyst:

    This reaction shows two carbons connected by a double bond, each with two bonded H atoms plus H O H arrow labeled “H subscript 3 O superscript plus” followed by two carbon atoms connected with a single bond with 5 bonded H atoms and an O H group shown in red at the right end of the molecule. The O of this group is shown with 2 pairs of electron dots.

    Alcohols containing two or more hydroxyl groups can be made. Examples include 1,2-ethanediol (ethylene glycol, used in antifreeze) and 1,2,3-propanetriol (glycerine, used as a solvent for cosmetics and medicines):

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    Compounds in which an OH group is attached directly to an aromatic ring are designated ArOH and called phenols. Phenols differ from alcohols in that they are slightly acidic in water. They react with aqueous sodium hydroxide (NaOH) to form salts.

    \[ArOH_{(aq)} + NaOH_{(aq)} \rightarrow ArONa_{(aq)} + H_2O\]

    The parent compound, C6H5OH, is itself called phenol. (An old name, emphasizing its slight acidity, was carbolic acid.) Phenol is a white crystalline compound that has a distinctive (“hospital smell”) odor.

     
    800px-Phenol-3D-balls.png Phenol_2_grams.jpg
    (Left) Structure of Phenol (right) Approximately two grams of phenol in glass vial. Image used with permisison from Wikipedia

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