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preface to fifteenth edition

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ORGANIC COMPOUNDS 1.35<br />

remain when each bridge is replaced by two hydrogen a<strong>to</strong>ms. The locant for 9CO9 is cited before<br />

that for the ester oxygen a<strong>to</strong>m. An additional carbon a<strong>to</strong>m is incorporated in<strong>to</strong> this structure as<br />

compared <strong>to</strong> the -olide.<br />

These trivial names are permitted: -butyrolac<strong>to</strong>ne, -valerolac<strong>to</strong>ne, and -valerolac<strong>to</strong>ne. Names<br />

based on heterocycles may be used for all lac<strong>to</strong>nes. Thus, -butyrolac<strong>to</strong>neis also tetrahydro-2-<br />

furanoneor dihydro-2(3H)-furanone.<br />

Lactides, intermolecular cyclic esters, are named as heterocycles. Lactams and lactims, containing<br />

a 9CO9NH9 and 9C(OH)"N9 group, respectively, are named as heterocycles, but they may<br />

also be named with -lactam or -lactim in place of -olide. For example,<br />

(1) 2-Pyrrolidinone<br />

(2) 4-Butanelactam<br />

1.1.3.20 Nitriles and Related Compounds. For acids whose systematic names end in -carboxylic<br />

acid, nitriles arenamed by adding thesuffix -carbonitrilewhen the9CN group replaces the<br />

9COOH group. Thecarbon a<strong>to</strong>m of the9CN group is excluded from the numbering of a chain<br />

<strong>to</strong> which it is attached. However, when the triple-bonded nitrogen a<strong>to</strong>m is considered <strong>to</strong> replace<br />

three hydrogen a<strong>to</strong>ms at the end of the main chain of an acyclic hydrocarbon, the suffix -nitrile is<br />

added <strong>to</strong> the name of the hydrocarbon. Numbering begins with the carbon attached <strong>to</strong> the nitrogen.<br />

For example, CH 3 CH 2 CH 2 CH 2 CH 2 CN is named (1) pentanecarbonitrile or (2) hexanenitrile.<br />

Trivial acid names are formed by changing the endings -oic acid or -ic acid <strong>to</strong> -onitrile. For<br />

example, CH 3 CN is ace<strong>to</strong>nitrile. When the 9CN group is not thehighest priority group, the9CN<br />

group is denoted by the prefix cyano-.<br />

In order of decreasing priority for citation of a functional class name, and the prefix for substitutive<br />

nomenclature, are the following related compounds:<br />

Functional group Prefix Radicofunctional ending<br />

9NC Isocyano- Isocyanide<br />

9OCN Cyana<strong>to</strong>- Cyanate<br />

9NCO Isocyana<strong>to</strong>- Isocyanate<br />

9ONC — Fulminate<br />

9SCN Thiocyana<strong>to</strong>- Thiocyanate<br />

9NCS Isothiocyana<strong>to</strong>- Isothiocyanate<br />

9SeCN Selenocyana<strong>to</strong>- Selenocyanate<br />

9NCSe Isoselenocyana<strong>to</strong>- Isoselenocyanate<br />

1.1.3.21 Peroxides. Compounds of thetypeR9O9OH arenamed (1) by placing thenameof<br />

theradical R beforetheword hydroperoxide or (2) by use of the prefix hydroperoxy- when another<br />

parent name has higher priority. For example, C 2 H 5 OOH is ethyl hydroperoxide.<br />

Compounds of thetypeR 1 O9OR 2 arenamed (1) by placing thenames of theradicals in alphabetical<br />

order before the word peroxide when the group 9O9O9 links two chains, two rings,<br />

or a ring and a chain, (2) by useof theaffix dioxy <strong>to</strong> denotethebivalent group 9O9O9 for<br />

naming assemblies of identical units or <strong>to</strong> form part of a prefix, or (3) by use of the prefix epidioxywhen<br />

the peroxide group forms a bridge between two carbon a<strong>to</strong>ms, a ring, or a ring system.

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