USING THE IUPAC SYSTEM

The following procedure should be followed to name alcohols according to the IUPAC system. 

Select the longest continuous carbon chain to which the hydroxyl group is attached. Change the name of the alkane corresponding to this chain by dropping the final -e and adding the suffix - ol. 

Number the carbon atoms in the longest continuous carbon chain starting from the end nearest to the hydroxyl group. The carbon atom bearing the hydroxyl group takes the lower number. Indicate the position of the hydroxyl 

For straight chained compounds, if the —OH is attached to the first carbon, instead of number 1 , the letter n , meaning normal, can be used. 

If the — OH group is attached to an unsaturated hydrocarbon chain, the number of the carbon bearing the —OH group is substituted between the name of hydrocarbon and the suffix -ol. If the —OH group is attached to the first carbon of the unsaturated hydrocarbon chain, the number of the carbon bearing the — OH group is not written. 

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Unsubstituted aliphatic dicarboxylic acids. HOOC (CH ) COOH. are most often referred to by their trivial names for n = 2 to 10 (Table I). Higher homologucs are named using the IUPAC system by adding the suffix dioic to the parent hydrocarbon. 

Name each of the following using the IUPAC system. 

Looking at periodic tables from different times and produced in different countries reveals a long history of scientific and political struggle. Even today, periodic tables demonstrate the creator s position regarding the control of chemistry by a governing body through its decision whether to use the IUPAC system or the names declared by the discoverers. Despite the various controversies, the periodic table of elements has become a standardized tool for education and research. It can be found as giant wall charts in classrooms and on wallet-size laminated plastic charts, and there are interactive versions on the Internet. It seems that the question of what the elements are and how they work has been answered. As far as everyday life is concerned, the elements listed on the periodic table really do constitute the matter that makes up the world around us, at least to element 92. 

Simple alcohols are named by the IUPAC system as derivatives of the parent alkane, using the suffix -ol. 

As noted in the text, chemists overwhelmingly use the nomenclature system devised and maintained by the International Union of Pure and Applied Chemistry, or IUPAC. Rules for naming monofunctional compounds were given throughout the text as each new functional group was introduced, and a list of where these rules can be found is given in Table A.l. 

In the/flc isomer, the three chloride ions are located on the corners of one of the triangular faces of the octahedron. In the mer isomer, the three chloride ions are located around an edge (meridian) of the octahedron. The IUPAC system of nomenclature does not use this approach. A summary of the IUPAC procedures is presented in the book by Huheey, Keiter, and Keiter that is cited in the references listed at the end of this chapter. 

In the IUPAC system locants are placed immediately before the part of the name to which they apply for instance subunits such as pyridine-2,4-diyl and l-methylpropane-l,3-diyl. One of the few exceptions is the phenylene subunit, for example, 1,4-phenylene in XV. The IUPAC nomenclature system is always evolving and some of the details (e.g., the names of some subunits) have changed in recent years. One should use caution when using less recent nomenclature references than those listed in this text. 

The IUPAC nomenclature system recognizes that most of the common (commercial) polymers have source-based or semisystematic names that are well established by usage. IPUAC does not intend that such names be supplanted by the IUPAC names but anticipates that such names will be kept to a minimum. The IUPAC system is generally used for all except the common polymers. The IUPAC names for various of the common polymers are indicated below the more established source or semisystematic name in the following ... 

Two further notes (1) Many transformations can be named using either of two reactants as the substrate. For example, the transformation methylene-de-oxo-bisubstitution above, can also be named ethylidene-de-triphenylphosphoranediyl-bisubstitution. In this book, unless otherwise noted, we will show only those names in which the substrate is considered to undergo the reactions indicated by the titles of the chapters. Thus the name we give to 1-12 (ArH + RCI- ArFt) is alkyl-de-hydrogenation, not aryl-de-chlorination, though the latter name is also perfectly acceptable under the IUPAC system. (2) The IUPAC rules recognize that some transformations are too complex to be easily fitted into the system, so they also include a list of names for some complex transformations, which are IUPAC approved, but nonsystematic (for some examples, see reactions 2-44, 8-36, 9-63). 

The nomenclature of boron hydride derivatives has been somewhat confusing and many inconsistencies exist in the literature. The structures of some reported boron hydride clusters are so complicated that only a structural drawing or graph, often accompanied by explanatory text, is used to describe them. Traditional nomenclature systems often can be used to describe compounds unambiguously, but the resulting descriptions may be so long and unwieldy that they are of litde use. The IUPAC (7) and the Chemical Abstract Service (8) have made recommendations, and nomenclature methods have now been developed that can adequately handle nearly all clusters compounds however, these methods have yet to be widely adopted. For the most part, nomenclature used in the original literature is retained herein. 

It is unfortunate that two systems of nomenclature are currently being used in this area. Though this author, like most in the United States, has a personal preference for the Fischer system (11) (because it retains a link with the monumental body of earlier work), the IUPAC system (12) is mandated in this chapter. To be sure, the IUPAC system has its advantages, not the least of which is the correlation of atoms between the porphyrin (12) and corrin (13) chromophore. 

In the IUPAC system, the four methine positions are conveniently numbered 5, 10, 15 and 20, and the eight remaining peripheral positions fall at 2, 3, 7, 8, 12, 13, 17 and 18. The nitrogen atoms are numbered 21 through 24. Owing to the continued use of trivial names, both in the IUPAC and classical systems of nomenclature, certain other features of porphyrin notation and isomerism need to be explained. If the eight peripheral substituents are made up of two sets of four (for example, four methyls and four ethyls), and if there is one of each on the individual pyrrole subunits (a situation which usually occurs in biologically derived porphyrins), then there are four possible so-called primary type isomers. These four isomers for the methyl/ethyl series, trivially named etioporphyrins, are shown in Scheme 1 the compounds are named etioporphyrin-I (14), etioporphyrin-II (15), etioporphyrin-III (16), and etioporphyrin-IV (17). 

Unfortunately, a completely systematic method of naming aromatic compounds is not in use. The system used is a combination of trivial names and the IUPAC system. Sometimes- compounds that contain benzene rings are considered to be substituted benzenes, in which case the word benzene appears in the name of the compound along with the name of the substituent. 

Ethylene glycol and propylene glycol are common names for these two diols and are acceptable IUPAC names. Aside from these two compounds, the IUPAC system does not use the word glycol for naming diols. 

Although epoxides are always considered to have their oxygen atom as part of a three-membered ring, the prefix epoxy in the IUPAC system of nomenclature can be used to denote a cyclic ether of various sizes. Thus... 

Systematic nomenclature (Section 2.11) Names for chemical compounds that are developed on the basis of a prescribed set of rules. Usually the IUPAC system is meant when the term systematic nomenclature is used. 

Since the new IUPAC recommendations [5], the nomenclature of quinic acid isomers is very confusing in the literature. Therefore, the latest IUPAC nomenclature is used throughout this paper instead of the older, but still useful, nomenclature. In the IUPAC nomenclature quinic acid is now treated as cyclitol. In the preferred configuration, the carboxy group and the C-4 and C-5 hydroxy groups are equatorial, with the C-l and C-3 hydroxy groups are axial. In the IUPAC system, the former 3-O-acylquinic acids are now renamed 5-O-compounds, and the... 

When a hydrocarbon is substituted with other than alkyl groups a new problem arises, which can be illustrated by CH3CH2C1. This substance can be called either chloroethane or ethyl chloride, and both names are used in conversation and in print almost interchangeably. In the IUPAC system, halogens, nitro groups, and a few other monovalent groups are considered to be substituent groups on hydrocarbons and are named as haloalkanes, nitro-alkanes, and so on. 

The IUPAC system for naming alkynes employs the ending -yne instead of the -ane used for naming of the corresponding saturated hydrocarbon ... 

Exercise 15-15 How can D-glucose, D-fructose, and D-ribose be considered products of the addition of an alcohol to the carbonyl group of an aldehyde or ketone Name each of the carbonyl compounds by the IUPAC system. For the ribose carbonyl structure, determine the configuration at each chiral center, using the D,L system. 

The system of naming now used was devised by the International Union of Pure and Applied Chemistry, abbreviated IUPAC. In the IUPAC system, a chemical name has three parts prefix, parent, and suffix. The parent name tells how many carbon atoms are present in the longest continuous chain the suffix identifies what family the molecule belongs to and the prefix (if needed) specifies the location of various substituent groups attached to the parent chain ... 

In the IUPAC system, use the following series of rules to name alcohols ... 

Aldehydes are named using either the common system or the IUPAC system. Aldehyde common names are derived from the common names of the corresponding carboxylic acid. For example ... 

Two systems are used for naming carboxylic acids the common system and the IUPAC system. 

Alcohols are compounds that contain a hydroxy group (—OH). Common names for simple alcohols use the name of the alkyl group followed by alcohol, such as ethyl alcohol or isopropyl alcohol. In the IUPAC system, alcohols are given the name of the hydrocarbon from which they are derived, with the suffix -ol replacing the final e of the name. The longest chain that contains the carbon bonded to the hydroxy group is chosen as the root and numbered so that this carbon has the lowest possible number. 

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