Simple ethers have simple common names, formed from the names of the groups attached to oxygen atom, followed by the generic name ether. For example, CH₃–O–CH₂CH₂CH₃ is methyl propyl ether. If both groups are the same, the group name should be preceded by the prefix di-, as in dimethyl ether (CH₃–O–CH₃) and diethyl ether CH₃CH₂–O–CH₂CH₃.  The IUPAC system names ethers by naming the longer end as an alkane and treating the shorter end as as an “alkoxy” substituent.  For example, CH₃–O–CH₂CH₂CH₃ is 1-methoxypropane.

Ether molecules have no hydrogen atom on the oxygen atom (that is, no OH group). Therefore there is no intermolecular hydrogen bonding between ether molecules, and ethers therefore have quite low boiling points for a given molar mass. Indeed, ethers have boiling points about the same as those of alkanes of comparable molar mass and much lower than those of the corresponding alcohols (Table 14.4 “Comparison of Boiling Points of Alkanes, Alcohols, and Ethers”).

Ether molecules do have an oxygen atom, however, and engage in hydrogen bonding with water molecules. Consequently, an ether has about the same solubility in water as the alcohol that is isomeric with it. For example, dimethyl ether and ethanol (both having the molecular formula C₂H₆O) are completely soluble in water, whereas diethyl ether and 1-butanol (both C₄H₁₀O) are barely soluble in water (8 g/100 mL of water).

To Your Health: Ethers as General Anesthetics

A general anesthetic acts on the brain to produce unconsciousness and a general insensitivity to feeling or pain. Diethyl ether (CH₃CH₂OCH₂CH₃) was the first general anesthetic to be used.

William Morton, a Boston dentist, introduced diethyl ether into surgical practice in 1846. This painting shows an operation in Boston in 1846 in which diethyl ether was used as an anesthetic. Inhalation of ether vapor produces unconsciousness by depressing the activity of the central nervous system.                                                                                                                                  Source: Painting of William Morton by Ernest Board, from http://commons.wikimedia.org/wiki/File:Morton_Ether_1846.jpg.

Diethyl ether is relatively safe because there is a fairly wide gap between the dose that produces an effective level of anesthesia and the lethal dose. However, because it is highly flammable and has the added disadvantage of causing nausea, it has been replaced by newer inhalant anesthetics, including the fluorine-containing compounds halothane, enflurane, and isoflurane. Unfortunately, the safety of these compounds for operating room personnel has been questioned. For example, female operating room workers exposed to halothane suffer a higher rate of miscarriages than women in the general population.

These three modern, inhalant, halogen-containing, anesthetic compounds are less flammable than diethyl ether.

Concept Review Exercises

1. Why does diethyl ether (CH₃CH₂OCH₂CH₃) have a much lower boiling point than 1-butanol (CH₃CH₂CH₂CH₂OH)?

2. Which is more soluble in water—ethyl methyl ether (CH₃CH₂OCH₃) or 1-butanol (CH₃CH₂CH₂CH₂OH)? Explain.

    

Show Answer

1. Diethyl ether has no intermolecular hydrogen bonding because there is no OH group; 1-butanol has an OH and engages in intermolecular hydrogen bonding.
2. Ethyl methyl ether (three carbon atoms, one oxygen atom) is more soluble in water than 1-butanol (four carbon atoms, one oxygen atom), even though both can engage in hydrogen bonding with water.  The longer the carbon hydrocarbon chains, the more the molecule acts like an insoluble alkane. 

Key Takeaways

• 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-.
• To give an ether its IUPAC name, name the longer hydrocarbon chain as an alkane and the shorter hydrocarbon chain with the oxygen as an “alkoxy” substituent.
• 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 the alcohol that is isomeric with it.