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Chemistry · Ch 11 — Alcohols, Phenols and Ethers

Nomenclature of Ethers

11.3.3

Nomenclature of Ethers

In the common (trivial) system of nomenclature, an ether is named by first writing the names of the two alkyl (or aryl) groups bonded to its oxygen atom in strict alphabetical order, and then adding the separate word 'ether' after them; if both groups happen to be identical, the prefix 'di-' is used instead of writing the group name twice (so CH3-O-CH3 is 'dimethyl ether', not 'methyl methyl ether'). According to the IUPAC system, ethers are instead named systematically as alkoxyalkanes: the LARGER of the two alkyl/aryl groups is treated as the parent alkane (or arene) chain, while the smaller group, together with its bridging oxygen, is expressed as an 'alkoxy' substituent prefix carrying its own numerical locant on that parent chain. Some common alkoxy-group names built this way include ethoxy (CH3-CH2-O-), n-propoxy (CH3-CH2-CH2-O-) and isopropoxy ((CH3)2CH-O-). Worked this way, CH3-O-CH3 becomes methoxymethane, CH3-O-CH2-CH3 becomes methoxyethane, C6H5-O-CH3 (anisole) becomes methoxybenzene, and …

Table 11.3Table 11.3 -- Common and IUPAC names of some ethers

Structural formula | Common name | IUPAC name: H3C-O-CH3 | Dimethyl ether | Methoxymethane. H3C-O-CH2CH3 | Ethyl methyl ether | Methoxyethane. H3C-O-CH2CH2CH3 | Methyl n-propyl ether | 1-Methoxypropane. C6H5-O-CH3 | Methyl phenyl ether (Anisole) | Methoxybenzene. C6H5-O-CH2CH2CH3 | Phenyl n-propyl ether | 1-Propoxybenzene. A cyclobutane ring bearing two methyl groups and one methoxy …

Figure 11.3.3aAlkoxy group names and IUPAC-named ether examples
Fig. 11.3.3a — Alkoxy group names and IUPAC-named ether examples

Drawn by us to help you understand the concept clearly, and verified to make sure it's accurate. For exams, practice from your textbook's own diagram.

What this figure shows. Lists the alkoxy-group fragments used as IUPAC substituent prefixes -- CH3-CH2-O- (ethoxy), CH3-CH2-CH2-O- (n-propoxy), and (CH3)2CH-O- (isopropoxy) -- and shows two additional worked IUPAC names built on this pattern: cyclobutanol-type cyclic alcohols named with a 'cyclo' prefix and the -OH carbon numbered C-1 (e.g. 2-ethylcyclopentanol, cyclobutanol), and 2-methoxypropane, CH3-O-CH(CH3)-CH3, as a straightforward alkoxyalkane example with the methoxy group at lo …