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preface to fifteenth edition

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1.18 SECTION 1<br />

Selection of the principal alicyclic chain or ring system is governed by these selection rules:<br />

1. For purely alicyclic compounds, the selection process proceeds successively until a decision is<br />

reached: (a) the maximum number of substituents corresponding <strong>to</strong> the characteristic group cited<br />

earliest in Table 1.7, (b) the maximum number of double and triple bonds considered <strong>to</strong>gether,<br />

(c) the maximum length of the chain, and (d) the maximum number of double bonds. Additional<br />

criteria, if needed for complicated compounds, are given in the IUPAC nomenclature rules.<br />

2. If the characteristic group occurs only in a chain that carries a cyclic substituent, the compound<br />

is named as an aliphatic compound in<strong>to</strong> which the cyclic component is substituted; a radical<br />

prefix is used <strong>to</strong> denote the cyclic component. This chain need not be the longest chain.<br />

3. If the characteristic group occurs in more than one carbon chain and the chains are not directly<br />

TABLE 1.7 Characteristic Groups for Substitutive Nomenclature<br />

Listed in order of decreasing priority for citation as principal group or parent name.<br />

1. Cations:<br />

2. Acids:<br />

Carboxylic<br />

Class Formula* Prefix Suffix<br />

H 4 N <br />

H 3 O <br />

H 3 S <br />

H 3 Se <br />

H 2 Cl <br />

H 2 Br <br />

H 2 I <br />

9COOH<br />

9(C)OOH<br />

9C("O)OOH<br />

-onio-<br />

Ammonio-<br />

Oxonio-<br />

Sulfonio-<br />

Selenonio-<br />

Chloronio-<br />

Bromonio-<br />

Iodonio-<br />

Carboxy-<br />

-onium<br />

-ammonium<br />

-oxonium<br />

-sulfonium<br />

-selenonium<br />

-chloronium<br />

-bromonium<br />

-iodonium<br />

-carboxylic acid<br />

-oic acid<br />

-peroxy···carboxylic<br />

acid<br />

9(C"O)OOH<br />

Sulfonic 9SO 3 H Sulfo- -sulfonic acid<br />

Sulfinic 9SO 2 H Sulfino- -sulfinic acid<br />

Sulfenic 9SOH Sulfeno- -sulfenic acid<br />

Salts<br />

3. Derivatives of<br />

acids:<br />

Anhydrides<br />

9COOM<br />

9(C)OOM<br />

9SO 3 M<br />

9SO 2 M<br />

9SOM<br />

-peroxy···oic acid<br />

Metal···carboxylate<br />

Metal···oate<br />

Metal···sulfonate<br />

Metal···sulfinate<br />

Metal···sulfenate<br />

9C("O)OC("O)9<br />

9(C"O)O(C"O)9<br />

-carboxylic anhydride<br />

-oic anhydride<br />

Esters<br />

9COOR<br />

9C(OOR)<br />

R-oxycarbonyl- R···carboxylate<br />

R···oate<br />

Acid halides 9CO9halogen Haloformyl -carbonyl halide<br />

Amides 9CO9NH 2<br />

(C)O9NH 2<br />

Carbamoyl- -carboxamide<br />

-amide

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