Alcohols, nomenclature secondary

Little further was substantiated about cholic acid (or about bile acids generally) for nearly five decades. The name, cholic acid, had become well established, but trivial names based partly on imperfect characterization were common, so that consideration of nomenclature was a part of Wieland s first report on the bile acids in 1912 (56). A review of the evidence then available included that cholic acid was a trihydroxy, monocarboxylic acid and that two of the alcohols were secondary. The final presentation of the structure of cholic acid awaited the correct steroid formulation in 1932 (113, 114). By that time the structural relationship between the sterols and bile acids was well established. The preparation of cholanic acid from cholic acid had been reported in the paper by Wieland and Weil in 1912 (56). The preparation of cholanic acid from cholesterol (through coprostane) was reported in 1919 by Windaus and Neukirchen (55). 

In the IUPAC system of nomenclature, the suffix for alcohols is -ol. Alcohols are classified as primary, secondary, or tertiary depending on whether one, two, or three organic groups are attached to the hydroxyl-bearing carbon. The nomenclature of alcohols and phenols is summarized in Secs. 7.1-7.3. 

The primary (1), secondary (2 ), tertiary (3) and quaternary (4) nomenclature is used in a number of situations to define a carbon centre, or to define functional groups like alcohols, halides, amines and amides. Identifying functional groups in this way can be important because the properties and reactivities of these groups vary depending on whether they are primary, secondary, tertiary or quaternary. 

From the Hg-containing alcohol in Figure 3.38 and NaBH4 one can obtain the Hg-free alcohol. The overall result is a hydration of the C=C double bond. According to the nomenclature of Section 3.3.3, its regioselectivity corresponds to a Markovnikov addition. It is complementary to the regioselectivity of the reaction sequence hydro-boration/oxidation/hydrolysis (Table 3.1). The latter sequence would have converted the same olefin regioselectively into the primary instead of the secondary alcohol. 

CDs are cyclic oligosaccharides containing 6, 7, or 8 glucopyranose units, referred to as a-, (3-, or y-CD, respectively. Each glucose unit contains two secondary alcohols at C-2 and C-3 and a primary alcohol at the C-6 position, providing 18-24 sites for chemical modification and derivatization (Fig. 2). Numerous derivatives have been prepared and described in the literature, but because of all the possible derivatives and positional and regioisomers, appropriate nomenclature must be used. The nomenclature should include at a minimum, the parent CD (a, (3, or y-CD) and the type and number of substituents. The substituents are usually noted by an abbreviation placed before the parent CD. Further description of the substituent group can be included with... 

This table should be completed by a table of the L-series, the members of which are enantiomers of those in Table 1. Remember that the D-series is defined by the orientation to the right of the secondary alcohol hydroxyl group with the highest-numbered atom. Sometimes the series descriptor is omitted for glucose, galactose, mannose, and ribose. In this case we must remember that they belong to the D-series. The recommended common names in Table 4.1 do not come from the systematic nomenclature. 

Name the following alcohols according to the lUPAC nomenclature system. Indicate stereochemistry (if any) and label the hydroxy groups as primary, secondary, or tertiary. 

The nomenclature of amines differs from that of the alcohols. The des nations primary, secondary, and tertiary refer to the number of substituents on the ammonia nitrogen ... 

There are two naturally occurring aldotetroses, D-erythrose and o-threose (16.49 and 16.50), and one ketotetrose, o-erythrulose (16.51). Erythrose and threose can be distinguished by nitric acid oxidation (notice the less usual but water-soluble oxidant, selective for the aldehyde and primary alcohol over the secondary alcohols) threose leads to a chiral diacid, while the diacid from erythrose is a meso-compound and achiral. Although, in a formal nomenclature sense, these diacids would be threaric acid and erythraric acid, they always go by their more common name of tartaric acid. 

Because of limitation of CD cavity size, the formation of more than the quarternary inclusion complex may be difficult. Of course, if hydrogen-binding components by primary or secondary hydroxyl of CD rims are counted the inclusion complex of more than quarternary may be possible. However, the nomenclature herein especially counts the components included within the cavity with CD. In fact, it is very difficult to discriminate the third or fourth components. They may vary with the goals investigated. For example, / -CD/a-naphthanol/l,2-bromoethane or )8-CD// -naphthanol/l,2-bromoethane system displays strong phosphorescence, and the various alcohol molecules affect obviously the lifetime observed, resulting in the recognition of alcohol molecules, as shown in Table 5 [60]. The alcohol molecules here are named as the fourth component. 

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