Organic Chemistry Text Book (CHEM 3401 and 3402)

Ethers are compounds having two alkyl or aryl groups bonded to an oxygen atom, as in the formula R¹–O–R². The ether functional group does not have a characteristic IUPAC nomenclature suffix, so it is necessary to designate it as a substituent. To do so the common alkoxy substituents are given names derived from their alkyl component, as shown in the table on the right below. Examples of ether nomenclature are provided on the left. Simple ethers are given common names in which the alkyl groups bonded to the oxygen are named in alphabetical order followed by the word "ether". The top left example shows the common name in blue under the IUPAC name. Many simple ethers are symmetrical, in that the two alkyl substituents are the same. These are named as "dialkyl ethers". Examples are: CH₃CH₂OCH₂CH₃, diethyl ether (sometimes referred to as ether), and CH₃OCH₂CH₂OCH₃, ethylene glycol dimethyl ether (glyme).

Alkyl Group Name   Alkoxy Group Name CH3– Methyl   CH3O– Methoxy CH3CH2– Ethyl   CH3CH2O–  Ethoxy (CH3)2CH– Isopropyl   (CH3)2CHO–  Isopropoxy (CH3)3C– tert-Butyl   (CH3)3CO–  tert-Butoxy C6H5– Phenyl   C6H5O–  Phenoxy

Sulfur analogs of ethers (R–S–R') are called sulfides. For example, (CH₃)₃C–S–CH₃ is tert-butyl methyl sulfide. Sulfides are chemically more reactive than ethers, reflecting the greater nucleophilicity of sulfur relative to oxygen.