14.S: Organic Compounds of Oxygen (Summary)

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To ensure that you understand the material in this chapter, you should review the meanings of the following bold terms in the summary and ask yourself how they relate to the topics in the chapter.

A functional group is any atom or atom group that confers characteristic properties to a family of compounds.

The hydroxyl group (OH) is the functional group of the alcohols. The alcohols are represented by the general formula ROH. Alcohols are derived from alkanes by replacing one or more hydrogen atoms by an OH group. A primary (1°) alcohol (RCH₂OH) has the OH group on a carbon atom attached to one other carbon atom; a secondary (2°) alcohol (R₂CHOH) has the OH group on a carbon atom attached to two other carbon atoms; and a tertiary (3°) alcohol (R₃COH) has the OH group on a carbon atom attached to three other carbon atoms.

The ability to engage in hydrogen bonding greatly increases the boiling points of alcohols compared to hydrocarbons of comparable molar mass. Alcohols can also engage in hydrogen bonding with water molecules, and those with up to about four carbon atoms are soluble in water.

Many alcohols can be synthesized by the hydration of alkenes. Common alcohols include methanol, ethanol, and isopropyl alcohol. Methanol is quite poisonous. It can cause blindness or even death. Ethanol can be prepared from ethylene or made by fermentation. It is the “alcohol” in alcoholic beverages. On occasion, people drink methanol by mistake, thinking it is the beverage alcohol. On occasion, unscrupulous bootleggers, sell methanol to unsuspecting customers. In either case, the results are often tragic.

Rubbing alcohol is usually a 70% aqueous solution of isopropyl alcohol. Ethanol is also used in some rubbing alcohol formulations.

When water is removed from an alcohol in a dehydration step, the result is either an alkene or an ether, depending on the reaction conditions. Primary alcohols are oxidized to aldehydes or carboxylic acids, and secondary alcohols are oxidized to ketones. Tertiary alcohols are not easily oxidized.

Alcohols containing two OH groups on adjacent carbon atoms are called glycols.

Phenols (ArOH) are compounds having the OH group attached to an aromatic ring.

Ethers (ROR′, ROAr, ArOAr) are compounds in which an oxygen atom is joined to two organic groups.

The carbonyl group, a carbon-to-oxygen double bond, is the defining feature of aldehydes and ketones. In aldehydes at least one bond on the carbonyl group is a carbon-to-hydrogen bond; in ketones, both available bonds on the carbonyl carbon atom are carbon-to-carbon bonds. Aldehydes are synthesized by the oxidation of primary alcohols. The aldehyde can be further oxidized to a carboxylic acid. Ketones are prepared by the oxidation of secondary alcohols. Mild oxidizing agents oxidize aldehydes to carboxylic acids. Ketones are not oxidized by these reagents.

A thiol is a compound with an SH functional group.