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ChemWiki: The Dynamic Chemistry E-textbook > Organic Chemistry > Ethers > Nomenclature of Ethers

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Nomenclature of Ethers

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 (below):

 

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

 

The smaller, shorter alkyl group becomes the alkoxy substituent. The larger, longer alkyl group side becomes the alkane base name. Each alkyl group on each side of the oxygen is numbered separately. The numbering priority is given to the carbon closest to the oxgen. The alkoxy side (shorter side) has an "-oxy" ending with its corresponding alkyl group. For example, CH3CH2CH2CH2CH2-O-CH2CH2CH3 is 1-propoxypentane. If there is cis or trans stereochemistry, the same rule still applies.

 

Example

Examples are: CH3CH2OCH2CH3, diethyl ether (sometimes referred to as ether), and CH3OCH2CH2OCH3, ethylene glycol dimethyl ether (glyme).

Common names

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".

Heterocycles

In cyclic ethers (heterocycles), one or more carbons are replaced with oxygen. Often, it's called heteroatoms, when carbon is replaced by an oxygen or any atom other than carbon or hydrogen. In this case, the stem is called the oxacycloalkane, where the prefix "oxa-" is an indicator of the replacement of the carbon by an oxygen in the ring. These compounds are numbered starting at the oxygen and continues around the ring. For example,

ex cred pic better.jpg

If a substituent is an alcohol, the alcohol has higher priority. However, if a substituent is a halide, ether has higher priority. If there is both an alcohol group and a halide, alcohol has higher priority. The numbering begins with the end that is closest to the higher priority substituent. There are ethers that are contain multiple ether groups that are called cyclic polyethers or crown ethers. These are also named using the IUPAC system.

Sulfides

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

References

  1. Schore, Neil E. and Vollhardt, K. Peter C. Organic Chemistry: Structure and Function. New York: Bleyer, Brennan, 2007.
  2. Winter, Arthur. Organic Chemistry for Dummies. Hoboken, New Jersey: Wiley, 2005.
  3. Pellegrini, Frank. Cliffs QuickReview Organic Chemistry II. Foster City, CA: Wiley, 2000

Problems

Name the following ethers:

ETHER PROBS.bmp

(Answers to problems above: 1. diethyl ether; 2. 2-ethoxy-2-methyl-1-propane; 3. cis-1-ethoxy-2-methoxycyclopentane;                                            4. 1-ethoxy-1-methylcyclohexane; 5. oxacyclopropane; 6. 2,2-Dimethyloxacyclopropane)

 

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Last Modified
09:25, 29 Jan 2014

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