No. 1, Volume 2 
January 1998

 
  Dr. Claff
 
A chemist-turned-translator, Dr. Claff earned his B.S. and Ph.D. degrees in Organic Chemistry at M.I.T. in 1950 and 1953. His academic and industrial research experience included the fields of organosodium chemistry, synthetic rubber, leather tanning and finishing, acrylic and vinyl polymerization, adhesives for coated abrasives, and flexographic printing inks. His career later evolved into corporate administration and management in metalworking, heart-lung machines, biological instrumentation, printing, personnel administration, and paper box manufacturing. His exposure to such diverse disciplines has been a valuable resource in his career as a freelance technical translator since 1974.
   Dr. Claff and his wife Eleanor make their home in Brockton, Massachusetts, with their Maine coon cats, DownE and Baxter.
  Dr. Claff can be reached at 74654.1335@compuserve.com

 
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A Translator’s Guide to Organic Chemical Nomenclature

Part X


by Chester E. Claff, Jr., Ph. D.
 
 
Download the zipped version of the first installments of this series, originally published in the Sci-Tech Translation Journal, of the American Translators Association. The file is approximately 87 KB.

Part IX of this series appeared in the October, 1997.issue of the Translation Journal.

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V. Organic Oxygen Compounds (continued)

Carboxylic Acids

In Part IX of this series we saw that compounds with two hydroxyl groups bonded to a terminal carbon atom split off a molecule of water spontaneously to form aldehydes. A similar process occurs when a terminal carbon atom carries three hydroxyl groups, giving rise to carboxylic acids as follows:

 

The carboxylic acids are usually written as RCO2H, RC(O)OH, or RC(=O)OH, where R can stand for any organic group. When R is an aliphatic group, the acids are called fatty acids. Depending on whether or not the group R contains one or more double bonds, the fatty acids can be saturated or unsaturated (referred to popularly as monounsaturated or polyunsaturated fatty acids).

Some of the more common fatty acids are described below in Table 11.

Table 11. Representative Fatty Acids
R Trivial
(Common)
Name
Systematic Name

H

Formic acid

Methanoic acid

CH3-

Acetic acid

Ethanoic acid

CH3CH2-

Propionic acid

Propanoic acid

CH3CH2CH2-

Butyric acid

Butanoic acid

n-C4H9-

Valeric acid

Pentanoic acid

n-C5H11-

Caproic acid

Hexanoic acid

n-C6H13-

Enanthic acid

Heptanoic acid

n-C7H15-

Caprylic acid

Octanoic acid

n-C8H17-

Pelargonic acid

Nonanoic acid

n-C9H19-

Capric acid

Decanoic acid

n-C11H23-

Lauric acid

Dodecanoic acid

n-C13H27-

Myristic acid

Tetradecanoic acid

n-C15H31-

Palmitic acid

Hexadecanoic acid

n-C17H35-

Stearic acid

Octadecanoic acid

n-C8H17CH=CH(CH2)7-

Oleic acid

cis-9-Octadecenoic acid

n-C5H11CH=CHCH2CH=CH(CH 2)7-

Linoleic acid

cis,cis-9,12-Octadecadienoic acid

  Some possible sources of confusion exist between caproic acid and capric acid, and between linoleic acid and linolenic acid (9,12,15-octadecatrienoic acid, which has three double bonds).
   Halogenated fatty acids are also common. Some examples are:
  chloroacetic acid ClCH2CO2H,
  trichloroacetic acid Cl3CCO2H,
  a-chloropropionic acid (2-chloropropanoic acid) CH3CHClCO2H,
  b-bromopropionic acid (3-bromopropanoic acid) BrCH2CH2CO2H,
  and
  g-iodobutyric acid (4-iodobutanoic acid) ICH2CH2CH2CO2H.

Note that locants can be of either type. The a-position, on the carbon adjacent to the carboxyl group, is the same as the 2-position.
  In German, Carbonsäure nearly always means carboxylic acid, not carbonic acid which is properly Kohlensäure. In compounds, -carbonsäure always means carboxylic acid and -säure means acid. Thus Essigsäure is acetic acid and Propionsäure is propionic acid. In the case of acetic acid, there are two German terms that require some explanation. Pure acetic acid freezes (and conversely melts) at just below room temperature (62°F, 16.7°C), and may thus be solid or liquid depending on laboratory conditions. Since it freezes so readily, pure acetic acid is called glacial acetic acid in English and Eisessig in German. Small amounts of water liquefy the substance, in which case it is called simply acetic acid or Essigsäure. Vinegar, of course, is dilute acetic acid.
  Locants for cyclic ethers are also designated as a, b, or g, or 2, 3, or 4 with respect to the oxygen atom. Thus furan can give rise to a-furoic acid (2-furancarboxylic acid) or b-furoic acid (3-furancarboxylic acid). Names such as 2-tetrahydrofurancarboxylic acid (2-carboxytetrahydrofuran) or analogous names for its 3-isomer are also acceptable.


Dicarboxylic Acids

Dicarboxylic acids are common in nature and in the laboratory, and have been given their own trivial names. They are used with diols to produce polyesters and are also used to produce polyamides (Nylon). Some of the common ones are listed below in Table 12.

Table 12. Representative Dicarboxylic Acids

  Chemical Structure

Trivial (Common) Name

HO2CCO2H

Oxalic acid

HO2CCH2CO2H

Malonic acid

HO2CCH2CH2CO2H

Succinic acid

cis-HO2CCH=CHCO2H

Maleic acid

trans-HO2CCH=CHCO2H

Fumaric acid

HO2C(CH2)3CO2 H

Glutaric acid

HO2C(CH2)4CO2 H

Adipic acid

HO2C(CH2)5CO2 H

Pimelic acid

HO2C(CH2)6CO2 H

Suberic acid

HO2C(CH2)7CO2 H

Azelaic acid

HO2C(CH2)8CO2 H

Sebacic acid

A simple mnemonic for remembering the names of the saturated aliphatic a,w-dicarboxylic acids is “Oh My, Such Good Apple Pie, Sweet As Sugar!” (This does not include the unsaturated maleic and fumaric acids).
 

Hydroxy Acids

Some of the simple hydroxy acids have also been given trivial names:

Table 13. Representative Hydroxy Acids

 HOCO2H

Carbonic acid

HOCH2CO2H

Glycolic acid

CH3CH(OH)CO2H

Lactic acid

HO2CCH(OH)CH2CO2H

Malic acid

HO2CCH(OH)CH(OH)CO2H

Tartaric acid

HO2CCH2C(OH)(CO2H)CH 2CO2H

Citric acid

Keto Acids

Some examples with trivial names are:

CH3C(=O)CO2H

Pyruvic acid

CH3C(=O)CH2CH2CO2H

Levulinic acid
HO2CCH2C(=O)CH2CO2H Acetonedicarboxylic acid
CH3C(=O)CH2CO2H Acetoacetic acid

 

Unsaturated Acids

In addition to maleic and fumaric acids (Table 12), some important unsaturated acids are:

CH2=CHCO2H

Acrylic acid

CH2=C(CH3)CO2H

Methacrylic acid

CH3CH=CHCO2H

Crotonic acid

HO2CCH2C(=CH2)CO2H

Itaconic acid

HO2CC(CH3)=CHCO2H

Citraconic acid

HO2CCH=C(CO2H)CH2CO2 H

Aconitic acid

HCºCCO2H

Propiolic acid

Acrylic and methacrylic acids are widely used in polymerization to prepare polyacrylic resins.
 

IN THE NEWS - Review your comprehension of Parts I to X:

The November 24, 1997, issue of Chemical & Engineering News reports:

“BP Chemicals to build butanediol plant...

BP Chemicals ... will build a $100 million, 140-million-lb-per-year 1,4-butanediol plant ... Geminox uses a direct dual-reactor route to produce 1,4-butanediol and its derivatives using butane instead of acetylene, butadiene, or propylene oxide, as do other technologies ... 1,4-Butanediol is used to make tetrahydrofuran, which is used to make fibers and solvents...”

We have discussed all of the organic chemicals mentioned in the extract above. Can you draw their structures and roughly understand how the processes might work? If so, you are on the way to being “chemistry-literate!” The terminology you have learned not only is of theoretical interest, but will help you to understand and appreciate practical industrial matters of current significance.
  Part XI will describe derivatives of carboxylic acids including esters, anhydrides, lactones, and salts.

Readers are urged to e-mail questions, comments, or suggestions for further topics in the field of organic nomenclature to the author at: 74654.1335@compuserve.com.


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