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Ethers

Ethers

Background:


The defining molecular structure for an ether is the central oxygen atom with two alkyl groups attached on either side.

Ether is named for, and popularly known as, the organic solvent originally used as an anesthetic in surgical procedures. This form is identified more correctly as diethyl ether or ethoxyethane. Dimethylether finds common use as a propellant in aerosol cans. Codeine is the methyl ether of morphine. These and other ethers find use in chemical processing, as a solvents, in insecticides, and as pharmacological reagents.

Physical Properties:


In general ethers they are less dense, less soluble in water, more volatile, and more inert than their parent alcohols.

Laboratory Preparation:


Ethers are the product of the dehydration of alcohol, where two molecules of alcohol connect through their OH functional groups, releasing H2O and leaving behind an interconnecting oxygen molecule situated between the two parent alkane chains.
conc H2SO4
2 CH3CH2-OH -------> CH3CH2-O-CH2CH3 + H2O

Naming Conventions:


The IUPAC convention for ethers is to create the name based on the names of the two alkane side chains.

The first part of the name is based on the shorter chain ... "meth", "eth", "prop" ... etc and the last part of the name is the name of the larger alkane. The middle part of the name is "oxy." Diethyl ether would be ethoxythane and dimethyl ether would be methoxymethane.

The common name for an either is derived again from the name for the alkane chains where "yl" is the suffix placed on the alkane name and the shorter alkane is named first.

CH3-O-CH2CH3

would be methylethyl ether.

History:


Ether was discovered in 1275 by Spanish chemist Raymundus Lullius and given the name "sweet vitriol." The first surgical anesthetic use of ether (ethoxyethane or diethyl ether) as an anesthetic is credited to Dr. Crawford Williamson Long, MD, age 27, of Jefferson, Georgia. On March 30, 1842, he removed one of the two tumors from the neck of Mr. James Venable under ether anesthesia.

Bibliography:


The Unusual History of Ether
Encyclopedia Britanica article on ether
Wikipedia article on ether
Perdue University - Discussion of Alcohols and Ethers

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