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Nomenclature of Ethers

    Table of contents
    1. 1. Introduction
    2. 2. References
    3. 3. Outside links
    4. 4. Problems

    Ethers are a class of organic compounds that contain an oxygen between two alkyl groups. They have the formula R-O-R', with R's being the alkyl groups. these compounds are used in dye, perfumes, oils, waxes and industrial use. Ethers are treated as alkanes and are named as alkoxyalkanes. The IUPAC system is used for naming ethers.

    1. 1. Introduction
    2. 2. References
    3. 3. Outside links
    4. 4. Problems

    Introduction

    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.

    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.

    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. methoxyethane; 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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