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Nomenclature of Ethers

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    824
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    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

    Ethers can be named by naming each of the two carbon groups as a separate word followed by a space and the word ether. The -OR group can also be named as a substituent using the group name, alkox

    Example \(\PageIndex{1}\)

    CH3-CH2-O-CH3 is called ethyl methyl ether or methoxyethane.

    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.

    Examples \(\PageIndex{2}\)
    • \(CH_3CH_2OCH_2CH_3\), diethyl ether (sometimes referred to as just ether)
    • \(CH_3OCH_2CH_2OCH_3\), ethylene glycol dimethyl ether (glyme).


    ethernom1.gif

    Exercises \(\PageIndex{2}\)

    Try to name the following compounds using these conventions:

    ether1.gif J

    ether2.gifJ

    Try to draw structures for the following compounds:

    • 2-pentyl 1-propyl ether J
    • 1-(2-propoxy)cyclopentene J

    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".

    • anisole (try naming anisole by the other two conventions. J )

    ether3.gif

    • oxirane

    ether4.gif

    1,2-epoxyethane, ethylene oxide, dimethylene oxide, oxacyclopropane,

    • furan (this compound is aromatic)

    ether5.gif

    tetrahydrofuran

    ether6.gif

    oxacyclopentane, 1,4-epoxybutane, tetramethylene oxide,

    • dioxane

    ether7.gif

    1,4-dioxacyclohexane

    Exercise \(\PageIndex{2}\)

    Try to draw structures for the following compounds-

    • 3-bromoanisole J
    • 2-methyloxirane J
    • 3-ethylfuran J

    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, e.g., (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.

    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)

    Exercise \(\PageIndex{3}\)
    What would you call Image

    (CC-BY; Dan Johnson via Twitter)

    Answer

    A one-eyed one-horned flying propyl people ether


    This page titled Nomenclature of Ethers is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by William Reusch.

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