A Translator’s Guide to Organic Chemical

Nomenclature
Part IX

by Chester E. Claff, Jr., Ph. D.

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V. Organic Oxygen Compounds (continued)

Structural Diagrams

It becomes burdensome and cluttered to represent each atom in complex molecules by

atomic symbols C, H, O, etc., accompanied by multiplying subscripts. A convenient
shorthand representation has evolved that is unequivocal, precise, and easily comprehended.
In these structural diagrams, all of the carbon-to-carbon bonds of a compound are shown as
straight line segments, either single, double, or triple. Carbon atoms are implied at all
intersections of line segments, at their ends, and at all vertices. Hydrogen atoms bonded to
carbon atoms are not shown, nor are carbon-to-hydrogen bonds; they are implied in such
number that the carbon valence of four is filled. All other hydrogen atoms (e.g. in hydroxyl
groups) are shown as H, and substituents on cyclic compounds are usually, but not
necessarily, shown in full.

Thus CH3CH2CH2CH3 becomes simply and

CH3C CCH3 becomes .

Atoms other than carbon and hydrogen are always represented by their symbols. Examples
are as follows:

= Chloroprene =

= trans-2-Butene =

= Ethylene oxide =

= Neopentane =

= n-Octane =

More Cyclic Ethers

Returning now to our main stream of thought, further representative examples of cyclic
ethers are shown below:

Propylene oxide Glycidol

Furan Tetrahydrofuran (THF)

Pyran Tetrahydropyran

Dioxane 1,4-Dioxin

2,3,7,8-Tetrachlorodibenzodioxin (TCDD). This is the

“dioxin” of pollution infamy.

Ketones and Aldehydes

Compounds with two hydroxyl groups bonded to a single carbon atom are unstable in
general. They split off a molecule of water spontaneously to form ketones or aldehydes
with an oxygen atom double-bonded to carbon:
 The product is a ketone, often written RCOR'.

The product is an aldehyde, often written RCHO.

Some common aldehydes are:

HCHO Formaldehyde; methanal

CH3CHO Acetaldehyde; ethanal
OHCCHO Glyoxal; ethanedial
CH3CH2CHO Propionaldehyde; propanal
CH2=CHCHO Acrolein; propenal
CH3(CH2)2CHO Butryaldehyde; butanal
CH3(CH2)3CHO Valeraldehyde; pentanal
(CH3)2CHCH2CHO Isovaleraldehyde; 3-methylbutanal
CH3(CH2)4CHO Caproaldehyde; hexanal

Furfural

Some representative ketones are:

Acetone; 2-propanone; 2-oxopropane; 2-ketopropane; dimethyl

CH3COCH3
ketone
ClCH2COCH3 Chloroacetone
Methyl ethyl ketone (MEK); 2-butanone; 2-oxobutane; 2-
CH3COCH2CH3
ketobutane
CH3COCH=CH2 Methyl vinyl ketone; 3-butenone
CH3COCH2COCH3 2,4-Pentanedione

Camphor; 2-camphanone

Review of Systematic Name Endings and Prefixes

The classes of compounds considered so far have the following systematic name endings:
-ane = Saturated aliphatic hydrocarbon
-ene = Aliphatic hydrocarbon containing a double bond
-yne = Aliphatic hydrocarbon containing a triple bond
-enyne = Aliphatic hydrocarbon containing both a double and a triple bond
-ol = Alcohol
-one = Ketone
-al = Aldehyde
-yl = Radical or group
-ylidene = Group disubstituted on a terminal carbon atom

Some of the systematic name prefixes we have mentioned are:

halo- = (Chloro-, bromo-, etc.) halogen-substituted
poly- = Polymeric
hydroxy- = HO-substituted
alkoxy- = RO-substituted
oxo- or = Containing an oxygen atom double-bonded to a carbon atom that in turn is
keto- bonded to two other carbon atoms

By now it must be abundantly clear that optional names exist for most organic compounds.

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.

© Copyright 1997 Gabe Bokor

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Updated 09/22/97