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LANGE'S HANDBOOK OF CHEMISTRY

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ORGANIC COMPOUNDS 1.31<br />

1.1.3.13 Ethers (R19O9R 2 ). In substitutivenomenclature, oneof thepossibleradicals,<br />

R9O9, is stated as the prefix to the parent compound that is senior from among R1 or R2 . Examples<br />

are methoxyethane for CH3OCH2CH3 and butoxyethanol for C4H9OCH2CH2OH. When another principal group has precedence and oxygen is linking two identical parent compounds,<br />

the prefix oxy- may be used, as with 2,2-oxydiethanol for HOCH2CH2OCH2CH2OH. Compounds of thetypeRO9Y9OR, where the two parent compounds are identical and contain<br />

a group having priority over ethers for citation as suffix, are named as assemblies of identical<br />

units. For example, HOOC9CH29O9CH2CH29O9CH29COOH is named 2,2-(ethylenedioxy)diacetic<br />

acid.<br />

Linear polyethers derived from three or more molecules of aliphatic dihydroxy compounds,<br />

particularly when the chain length exceeds ten units, are most conveniently named by open-chain<br />

replacement nomenclature. For example, CH3CH29O9CH2CH29O9CH2CH3 could be3,6dioxaoctane<br />

or (2-ethoxy)ethoxyethane.<br />

An oxygen atom directly attached to two carbon atoms already forming part of a ring<br />

system or to two carbon atoms of a chain may be indicated by the prefix epoxy-. For example,<br />

CH29CH9CH2Cl is named 1-chloro-2,3-epoxypropane.<br />

O<br />

Symmetrical linear polyethers may be named (1) in terms of the central oxygen atom when there<br />

is an odd number of ether oxygen atoms or (2) in terms of the central hydrocarbon group when there<br />

is an even number of ether oxygen atoms. For example, C2H59O9C 4H89O9C 4H89O9C 2H5 is bis-(4-ethoxybutyl)ether, and 3,6-dioxaoctane (earlier example) could be named 1,2bis(ethoxy)ethane.<br />

Partial ethers of polyhydroxy compounds may be named (1) by substitutive nomenclature or (2)<br />

by stating thenameof thepolyhydroxy compound followed by thenameof theetherifying radical(s)<br />

followed by the word ether. For example,<br />

(1) 3-Butoxy-1,2-propanediol<br />

(2) Glycerol 1-butyl ether; also, 1-O-butylglycerol<br />

Cyclic ethers are named either as heterocyclic compounds or by specialist rules of heterocyclic<br />

nomenclature. Radicofunctional names are formed by citing the names of the radicals R 1 and R 2<br />

followed by the word ether. Thus methoxyethane becomes ethyl methyl ether and ethoxyethane<br />

becomes diethyl ether.<br />

1.1.3.14 Halogen Derivatives. Using substitutive nomenclature, names are formed by adding<br />

prefixes listed in Table 1.8 to the name of the parent compound. The prefix perhalo- implies the<br />

replacement of all hydrogen atoms by the particular halogen atoms.<br />

Cations of thetypeR 1 R 2 X are given names derived from the halonium ion, H 2X , by substitution,<br />

e.g., diethyliodonium chloride for (C 2H 5) 2I Cl .<br />

Retained are these trivial names; bromoform (CHBr 3), chloroform (CHCl 3), fluoroform (CHF 3),<br />

iodoform (CHI 3), phosgene (COCl 2), thiophosgene (CSCl 2), and dichlorocarbene radical ( CCl 2).<br />

Inorganic nomenclature leads to such names as carbonyl and thiocarbonyl halides (COX 2 and CSX 2)<br />

and carbon tetrahalides (CX 4).<br />

1.1.3.15 Hydroxylamines and Oximes. For RNH9OH compounds, prefix the name of the radical<br />

R to hydroxylamine. If another substituent has priority as principal group, attach the prefix

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