6: Organic Compounds of Oxygen and Nitrogen
- Page ID
- 444332
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Ethanol and resveratrol, a phenol, are representatives of two of the families of oxygen-containing compounds that we consider in this chapter. Two other classes, aldehydes and ketones, are formed by the oxidation of alcohols. Ethers, another class, are made by the dehydration of alcohols.
- 6.1: 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.
- 6.2: 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.
- 6.3: 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.
- 6.4: 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.
- 6.5: Aldehydes and Ketones- Structure and Names
- The common names of aldehydes are taken from the names of the corresponding carboxylic acids: formaldehyde, acetaldehyde, and so on. The common names of ketones, like those of ethers, consist of the names of the groups attached to the carbonyl group, followed by the word ketone. Stem names of aldehydes and ketones are derived from those of the parent alkanes, using an -al ending for an aldehydes and an -one ending for a ketone.
- 6.6: Properties of Aldehydes and Ketones
- The polar carbon-to-oxygen double bond causes aldehydes and ketones to have higher boiling points than those of ethers and alkanes of similar molar masses but lower than those of comparable alcohols that engage in intermolecular hydrogen bonding. Aldehydes are readily oxidized to carboxylic acids, whereas ketones resist oxidation.
- 6.7: 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
- 6.8: Carboxylic Acids - Structures and Names
- Simple carboxylic acids are best known by common names based on Latin and Greek words that describe their source (e.g., formic acid, Latin formica, meaning “ant”). Greek letters, not numbers, designate the position of substituted acids in the common naming convention. IUPAC names are derived from the LCC of the parent hydrocarbon with the -e ending of the parent alkane replaced by the suffix -oic and the word acid.
- 6.10: Esters - Structures and Names
- An ester has an OR group attached to the carbon atom of a carbonyl group.
- 6.11: Amines - Structures and Names
- An amine is a derivative of ammonia in which one, two, or all three hydrogen atoms are replaced by hydrocarbon groups. Amines are classified as primary, secondary, or tertiary by the number of hydrocarbon groups attached to the nitrogen atom. Amines are named by naming the alkyl groups attached to the nitrogen atom, followed by the suffix -amine.
- 6.12: Amines as Bases
- Amines are bases; they react with acids to form salts. Salts of aniline are properly named as anilinium compounds, but an older system is used to name drugs: the salts of amine drugs and hydrochloric acid are called “hydrochlorides.” Heterocyclic amines are cyclic compounds with one or more nitrogen atoms in the ring.
- 6.13: Amides- Structures and Names
- Amides have a general structure in which a nitrogen atom is bonded to a carbonyl carbon atom. In names for amides, the -ic acid of the common name or the -oic ending of the IUPAC for the corresponding carboxylic acid is replaced by -amide.