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preface to fifteenth edition

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ORGANIC COMPOUNDS 1.3<br />

ethane becomes the radical ethyl. These exceptions are permitted for unsubstituted radicals<br />

only:<br />

Isopropyl (CH 3 ) 2 CH9 Isopentyl (CH 3 ) 2 CHCH 2 CH 2 9<br />

Isobutyl (CH 3 ) 2 CHCH 2 9 Neopentyl (CH 3 ) 3 CCH 2 9<br />

sec-Butyl CH 3 CH 2 CH(CH 3 )9 tert-Pentyl CH 3 CH 2 C(CH 3 ) 2 9<br />

tert-Butyl (CH 3 ) 3 C9 Isohexyl (CH 3 ) 2 CHCH 2 CH 2 CH 2 9<br />

Note the usage of the prefixes iso-, neo-, sec-, and tert-, and note when italics are employed. Italicized<br />

prefixes are never involved in alphabetization, except among themselves; thus sec-butyl would precede<br />

isobutyl, isohexyl would precede isopropyl, and sec-butyl would precede tert-butyl.<br />

Examples of alkane nomenclature are<br />

2-Methylbutane (or the trivial name, isopentane)<br />

3-Methylpentane (not 2-ethylbutane)<br />

5-Ethyl-2,2-dimethyloctane (note cited order)<br />

3-Ethyl-6-methyloctane (note locants reversed)<br />

4,4-Bis(1,1-dimethylethyl)-2-methyloctane<br />

4,4-Bis-1,1-dimethylethyl-2-methyloctane<br />

4,4-Bis(tert-butyl)-2-methyloctane<br />

Bivalent radicals derived from saturated unbranched alkanes by removal of two hydrogen a<strong>to</strong>ms<br />

are named as follows: (1) If both free bonds are on the same carbon a<strong>to</strong>m, the ending -ane of the<br />

hydrocarbon is replaced with -ylidene. However, for the first member of the alkanes it is methylene

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