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Chemistry LibreTexts

3: Alcohols, Phenols, Thiols, and Ethers

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    • 3.1: Prelude to Organic Compounds of Oxygen
      One of the more familiar chemical compounds on Earth is ethyl alcohol (ethanol). As the intoxicant in alcoholic beverages, ethanol is often simply called alcohol. If ethanol is diluted, as it is in wine, beer, or mixed drinks with about 1 oz of liquor, and if it is consumed in small quantities, it is relatively safe. In excess—four or more drinks in a few hours—it causes intoxication, which is characterized by a loss of coordination, nausea and vomiting, and memory blackouts.
    • 3.2: Organic Compounds with Functional Groups
      The functional group, a structural arrangement of atoms and/or bonds, is largely responsible for the properties of organic compound families.
    • 3.3: Alcohols - Nomenclature and Classification
      In the IUPAC system, alcohols are named by changing the ending of the parent alkane name to -ol. Alcohols are classified according to the number of carbon atoms attached to the carbon atom that is attached to the OH group.
    • 3.4: Physical Properties of Alcohols
      Alcohols have higher boiling points than do ethers and alkanes of similar molar masses because the OH group allows alcohol molecules to engage in hydrogen bonding. Alcohols of four or fewer carbon atoms are soluble in water because the alcohol molecules engage in hydrogen bonding with water molecules; comparable alkane molecules cannot engage in hydrogen bonding.
    • 3.5: Reactions that Form Alcohols
      Many alcohols are made by the hydration of alkenes. Ethanol can be made by the fermentation of sugars or starch from various sources.
    • 3.6: Reactions of Alcohols
      Alcohols can be dehydrated to form either alkenes (higher temperature, excess acid) or ethers (lower temperature, excess alcohol). Primary alcohols are oxidized to form aldehydes. Secondary alcohols are oxidized to form ketones. Tertiary alcohols are not readily oxidized.
    • 3.7: Glycols and Glycerol
      Glycols are alcohols with two OH groups on adjacent carbon atoms. Glycerol is the most important trihydroxy alcohol.
    • 3.8: Phenols
      Phenols are compounds in which an OH group is attached directly to an aromatic ring. Many phenols are used as antiseptics.
    • 3.9: Organic Sulfur Compounds
      Thiols, thioethers, and disulfides are common in biological compounds.
    • 3.10: Ethers
      To give ethers common names, simply name the groups attached to the oxygen atom, followed by the generic name ether. If both groups are the same, the group name should be preceded by the prefix di-. Ether molecules have no OH group and thus no intermolecular hydrogen bonding. Ethers therefore have quite low boiling points for a given molar mass. Ether molecules have an oxygen atom and can engage in hydrogen bonding with water molecules. An ether molecule has about the same solubility in water as

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