ALCOHOLS, ETHERS, AND THIOLS

DIOL - A compound containing two -OH (hydroxyl) groups.

GLYCOL - A compound with hydroxyl (-OH) groups on adjacent carbons.

DEHYDRATION - Elimination of a molecule of water from an alcohol. In the dehydration of an alcohol,

OH is removed from one carbon and an H is removed from an adjacent carbon.

ETHER - A compound containing an oxygen atom bonded to two carbon atoms.

CYCLIC ETHER - An ether in which the ether oxygen is one of the atoms of a ring.

THIOL - A compound that contains an -SH (sulfhydryl) group bonded to a tetrahedral carbon atom.

MERCAPTAN - A common name for any molecule containing an -SH group. Mercaptan, which literally
means “mercury capturing.”

DISULFIDE - A compound containing an (-S-S-) group.

ACID-CATALYZED DEHYDRATION OF AN ALCOHOL - When isomeric alkenes are possible, the major
product is generally the more substituted alkene.

OXIDATION OF A PRIMARY ALCOHOL - Oxidation of a primary alcohol by potassium dichromate gives

either an aldehyde or a carboxylic acid, depending on the experimental conditions.
OXIDATION OF A SECONDARY ALCOHOL - Oxidization of a secondary alcohol by potassium dichromate
gives a ketone.

ACIDITY OF THIOLS - Thiols are weak acids, with pKa values of approximately 10. They react with strong
bases to form water-soluble thiolate salts.

OXIDATION OF A THIOL TO A DISULFIDE - Oxidation of a thiol gives a disulfide. Reduction of a disulfide

gives two thiols.