Acyclic Hydrocarbons Rule A-1.

Saturated Unbranched-chain Compounds and Univalent Radicals

1.1 - The first four saturated unbranched acyclic hydrocarbons are called methane, ethane, propane and butane. Names of the higher members of this series consist of a numerical term, followed by "-ane" with elision of terminal "a" from the numerical term. Examples of these names are shown in the table below. The generic name of saturated acyclic hydrocarbons (branched or unbranched) is "alkane". Examples of names: (n = total number of carbon atoms) n N 1 Methane 22 Docosane 2 Ethane 23 Tricosane 3 Propane 24 Tetracosane 4 Butane 25 Pentacosane 5 Pentane 26 Hexacosane 6 Hexane 27 Heptacosane 7 Heptane 28 Octacosane 8 Octane 29 Nonacosane 9 Nonane 30 Triacontane 10 Decane 31 Hentriacontane 11 Undecane 32 Dotriacontane 12 Dodecane 33 Tritriacontane 13 Tridecane 40 Tetracontane 14 Tetradecane 50 Pentacontane 15 Pentadecane 60 Hexacontane 16 Hexadecane 70 Heptacontane 17 Heptadecane 80 Octacontane 18 Octadecane 90 Nonacontane 19 Nonadecane 100 Hectane 132 Dotriacontahectane 20 Icosane 21 Henicosane 1.2 - Univalent radicals derived from saturated unbranched acyclic hydrocarbons by removal of hydrogen from a terminal carbon atom are named by replacing the ending "-ane" of the name of the hydrocarbon by "-yl". The carbon atom with the free valence is numbered as 1. As a class, these radicals are called normal, or unbranched chain, alkyls.
Examples to Rule A-1.2

See Recommendations'93 R-2.2.1

Parent Hydrides R-2.2.1 Hydrocarbons

The saturated unbranched acyclic hydrocarbons from C2 to C4 are named ethane, propane, and butane (see R-9.1, Table 19(a)). Systematic names of the higher members of this series consist of a numerical term (see Table 11), followed by "-ane" with elision of a terminal 'a' from the basic numerical term. The generic name for saturated acyclic hydrocarbons (branched or unbranched) is "alkane". The chain is numbered from one end to the other with arabic numerals.
Examples to R-2.2.1

R-2.2.2 Homogeneous hydrides other than hydrocarbons or boron hydrides

A compounds consisting of a unbranched chain containing several identical heteroatoms saturated with hydrogen atoms, may be names by citing the appropriate multiplying prefix (with no elision of the terminal vowel of the multiplying prefix) followed by the appropriate name of the hydride according to R-2.1. If necessary, a symbol is used, according to R-1.1.
Examples to R-2.2.2

R-2.2.3 Heterogeneous hydrides

R-2.2.3.1 Heterogeneous hydrides consisting of chains containing carbon atom and several heteroatoms, alike or different, and terminating with carbon may be named by replacement nomenclature (see R-1.2.2).
Example to R-2.2.3.1

R-2.2.3.2 Compounds containing an unbranched chain of alternating atom terminated by two identical atoms of the element coming later in Table 3 (see R-2.3.3.3) may be named by citing successively a multiplying prefix denoting the number of atoms of the terminating element followed by the "a" term of that element (see R-9.3), then the "a" term of the other element of the chain and the ending "-ane". The terminal letter "a" of an "a" term is elided when followed by a vowel; the terminal vowel of a numerical prefix is not elided even when the "a" term begins with the same vowel.
Examples to R-2.2.3.2

Rule A-2. Saturated Branched-chain Compounds and Univalent Radicals

2.1 - A saturated branched acyclic hydrocarbon is named by prefixing the designations of the side chains to the name of the longest chain present in the formula.
Example to Rule A-2.1

The following names are retained for unsubstituted hydrocarbons only: Isobutane

Isopentane

Neopentane

Isohexane

2.2 - The longest chain is numbered from one end to the other by Arabic numerals, the direction being so chosen as to give the lowest numbers possible to the side chains. When series of locants containing the same number of terms are compared term by term, that series is "lowest" which contains the lowest number on the occasion of the first difference. This principle is applied irrespective of the nature of the substituents.
Examples to Rule A-2.2

2.25 - Univalent branched radicals derived from alkanes are named by prefixing the designation of the side chains to the name of the unbranched alkyl radical possessing the longest possible chain starting from the carbon atom with the free valence, the said atom being numbered as 1.
Examples to Rule A-2.25

1-Methylpentyl 2-Methylpentyl 5-Methylhexyl The following names may be used for the unsubstituted radicals only: Isopropyl

Isobutyl

sec-Butyl

tert-Butyl

Isopentyl

Neopentyl

tert-Pentyl

Isohexyl

2.3 - If two or more side chains of different nature are present, they are cited in alphabetical order . The alphabetical order is decided as follows: (i) The names of simple radicals are first alphabetized and the multiplying prefixes are then inserted.
Examples to Rule A-2.3(i)

ethyl is cited before methyl, thus 4-Ethyl-3,3-dimethylheptane (ii) The name of a complex radical is considered to begin with the first letter of its complete name.
Examples to Rule A-2.3(ii)

dimethylpentyl (as complete single substituent) is alphabetized under "d", thus 7-(1,2-Dimethylpentyl)-5-ethyltridecane (iii) In cases where names of complex radicals are composed of identical words, priority for citation is given to that radical which contains the lowest locant at the first cited point of difference in the radical.
Examples to Rule A-2.3(iii)

2.4 - If two or more side chains are in equivalent positions, the one to be assigned the lower number is that cited first in the name.
Examples: to Rule A-2.4

2.5 - The presence of identical unsubstituted radicals is indicated by the appropriate multiplying prefix di-, tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, deca-, undeca, etc.
Example to Rule A-2.5(a)

The presence of identical radicals each substituted in the same way may be indicated by the appropriate multiplying prefix bis-, tris-, tetrakis-, pentakis-, etc. The complete expression denoting such a side chain may be enclosed in parentheses or the carbon atoms in side chains may be indicated by primed numbers.
Examples to Rule A-2.5(b)

(a) Use of parentheses and unprimed numbers: 5,5-Bis(1,1-dimethylpropyl)-2-methyldecane (b) Use of primes: 5,5-Bis-1',1'-dimethylpropyl-2-methyldecane

(a) Use of parentheses and unprimed numbers: 7-(1,1-Dimethylbutyl)-7-(1,1-dimethylpentyl)tridecane (b) Use of primes: 7-1',1'-Dimethylbutyl-7-1",1"-dimethylpentyltridecane 2.6 - If chains of equal length are competing for selection as main chain in a saturated branched acyclic hydrocarbon, then the choice goes in series to: (a) The chain which has the greatest number of side chains.
Example to Rule A-2.6(a)

(b) The chain whose side chains have the lowest-numbered locants.
Example to Rule A-2.6(b)

(c) The chain having the greatest number of carbon atoms in the smaller side chains.
Example to Rule A-2.6(c)

(d) The chain having the least branched side chains.

Example to Rule A-2.6(d)

Rule A-3. Unsaturated Compounds and Univalent Radicals

3.1 - Unsaturated unbranched acyclic hydrocarbons having one double bond are named by replacing the ending "-ane" of the name of the corresponding saturated hydrocarbon with the ending "-ene". If there are two or more double bonds, the ending will be "-adiene", "-atriene", etc. The generic names of these hydrocarbons (branched or unbranched) are "alkene", "alkadiene", "alkatriene", etc. The chain is so numbered as to give the lowest possible numbers to the double bonds. When, in cyclic compounds or their substitution products, the locants of a double bond differ by unity, only the lower locant is cited in the name; when they differ by more than unity, one locant is placed in parentheses after the other (see Rules A31.3 and A-31.4).
Examples to Rule A-3.1

2-Hexene 1,4-Hexadiene The following non-systematic names are retained: Ethylene Allene 3.2 - Unsaturated unbranched acyclic hydrocarbons having one triple bond are named by replacing the ending "-ane" of the name of the corresponding saturated hydrocarbon with the ending "-yne". If there are two or more triple bonds, the ending will be "-adiyne", "atriyne", etc. The generic names of these hydrocarbons (branched or unbranched) are "alkyne", "alkadiyne", "alkatriyne", etcThe chain is so numbered as to give the lowest possible numbers to the triple bonds. Only the lower locant for a triple bond is cited in the name of a compound. The name "acetylene" for is retained.

3.3 - Unsaturated unbranched acyclic hydrocarbons having both double and triple bonds are named by replacing the ending "-ane" of the name of the corresponding saturated hydrocarbon with the ending "-enyne", "-adienyne", "-atrienyne", "-enediyne", etcNumbers as low as possible are given to double and triple bonds even though this may at times give "yne" a lower number than "-ene". When there is a choice in numbering, the double bonds are given the lowest numbers.
Examples to Rule A-3.3

1,3-Hexadien-5-yne 3-Penten-1-yne 1-Penten-4-yne 3.4 - Unsaturated branched acyclic hydrocarbons are named as derivatives of the unbranched hydrocarbons which contain the maximum number of double and triple bonds. If there are two or more chains competing for selection as the chain with the maximum number of unsaturated bonds, then the choice goes to (1) that one with the greatest number of carbon atoms; (2) the number of carbon atoms being equal, that one containing the maximum number of double bonds. In other respects, the same principles apply as for naming saturated branched acyclic hydrocarbons. The chain is so numbered as to give the lowest possible numbers to double and triple bonds in accordance with Rule A-3.3.
Examples to Rule A-3.4

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The following name is retained for the unsubstituted compound only:

3.5 - The names of univalent radicals derived from unsaturated acyclic hydrocarbons have the endings "-enyl", "-ynyl", "-dienyl", etc., the positions of the double and triple bonds being indicated where necessary. The carbon atom with the free valence is numbered as 1.
Examples to Rule A-3.5

Ethynyl 2-Propynyl 1-Propenyl 2-Butenyl 1,3-Butadienyl 2-Pentenyl 2-Penten-4-ynyl Exceptions: The following names are retained (for unsubstituted radical only): Vinyl (for ethenyl)
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Allyl (for 2-propenyl) Isopropenyl(for 1-methylvinyl)

3.6 - When there is a choice for the fundamental chain of a radical, that chain is selected which contains (1) the maximum number of double and triple bonds; (2) the largest number of carbon atoms; and (3) the largest number of double bonds.
Examples to Rule A-3.6

See Recommendations'93 R-3.1.1

Characteristic (Functional) Groups R-3.1.1 Suffixes denoting multiple bonds

The presence of one or more double or triple bonds in an otherwise saturated parent hydride (except for parent hydrides with Hantzsch-Widman names) is denoted by changing the "-ane" ending of the name of a saturated parent hydride to one of the following: One Double bond Triple bond -ene -yne Two -adiene -adiyne Three -atriene -atriyne etc. etc. etc.

The presence of both double and triple bonds is similarly denoted by endings such as "12

enyne", "-adienyne", "-enediyne", etc. Numbers as low as possible are given to double and triple bonds as a set, even though this may at times give "-yne" a lower number than "-ene". If a choice remains, preference for low locants is given to the double bonds. Only the lower locant for a multiple bond is cited except when the numerical difference between the two locants is greater than one, in which case the higher-numbered locant is cited in parentheses (see R-0.1.4).
Examples to R-3.1.1

Use of these ending is further illustrated in Sections R-4 and R-5 (see also the 1979 edition of the IUPAC Nomenclature of Organic Chemistry , Rule A-3).

R-3.1.2 Hydro prefixes

If the name of the parent hydride implies the presence of the maximum number of noncumulative double bonds (see R-2.4.1), other states of hydrogenation can usually be indicated by use of the prefix "hydro-" together with an appropriate numerical prefix signifying the addition of hydrogen atoms. This operation is regarded as the reduction of double bonds; thus, hydrogen atoms can only be added in pairs (by use of "dihydro-", "tetrahydro-", etc.). "Indicated hydrogen" (see R-1.3) is included if required by the parent hydride.
Examples to R-3.1.2

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R-3.1.3 Dehydro prefixes

The presence of a double bond not implied in the parent hydride name can be indicated by a "didehydro-" prefix signifying the removal of a pair of hydrogen atoms.
Examples to R-3.1.3

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Similarly, the conversion of a double into a triple bond can be indicated by "didehydro-".
Example to R-3.1.3

(see also 7,8-Didehydro- , -carotene under R-1.2.5.1).

R-3.1.4 Substituent prefix names for unsaturated/saturated parent hydrides

When derived according to R-3.1.1, R-3.1.2 and R-3.1.3 above, these are formed by replacing the final "e" of the name of the unsaturated/saturated structure by an appropriate suffix given in R-2.5. Free valence position are preferred to positions of unsaturation denoted by the suffixes "ene", etc., for low locant numbers . As with substituent prefixes derived from saturated parent hydrides (see R-2.1), the free valences can be at any position on the parent structure.
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Accordingly, for acyclic unsaturated parent structures, all locants for the free valences, including "1", must be cited.
Examples to R-3.1.4

Rule A-4. Bivalent and Multivalent Radicals

4.1 - Bivalent and trivalent radicals derived from univalent acyclic hydrocarbon radicals whose authorized names end in "-yl" by removal of one or two hydrogen atoms from the carbon atom with the free valences are named by adding "-idene" or "-idyne", respectively, to the name of the corresponding univalent radical. The carbon atom with the free valence is numbered as 1. The name "methylene" is retained for the radical
Examples to Rule A-4.1

Methylidyne Ethylidene Ethylidyne Vinylidene Isopropylidene 4.2 - The names of bivalent radicals derived from normal alkanes by removal of a hydrogen atom from each of the two terminal carbon atoms of the chain are ethylene, trimethylene, tetramethylene, etc.
Examples to Rule A-4.2

Pentamethylene

16

Hexamethylene Names of the substituted bivalent radicals are derived in accordance with Rules A-2.2 and A2.25.
Example to Rule A-4.2a

The following name is retained:

4.3 - Bivalent radicals similarly derived from unbranched alkenes, alkadienes, alkynes, etc., by removing a hydrogen atom from each of the terminal carbon atoms are named by replacing the endings "-ene", "-diene", "-yne", etc., of the hydrocarbon name by "-enylene", "-dienylene", "-ynylene", etc., the positions of the double and triple bonds being indicated where necessary.
Example to Rule A-4.3

The following name is retained:

Names of the substituted bivalent radicals are derived in accordance with Rule A-3.4.
Example to Rule A-4.3

4.4 - Trivalent, quadrivalent and higher-valent acyclic hydrocarbon radicals of two or more carbon atoms with the free valences at each end of a chain are named by adding to the hydrocarbon name the terminations "-yl" for a single free valence, "-ylidene" for a double, and "-ylidyne" for a triple free valence on the same atom (the final "e" in the name of the hydrocarbon is elided when followed by a suffix beginning with "-yl"). If different types are present in the same radical, they are cited and numbered in the order "-yl", "-ylidene", "ylidyne".
Examples to Rule A-4.4

Butanediylidene Butanediylidyne 1-Propanyl-3-ylidene

17

Propadienediylidene 2-Pentenediylidyne 1-Butanyliden-4-ylidyne 4.5 - Multivalent radicals containing three or more carbon atoms with free valences at each end of a chain and additional free valences at intermediate carbon atoms are named by adding the endings "-triyl", "-tetrayl", "-diylidene", "diyl-ylidene", etc., to the hydrocarbon name.
Examples to Rule A-4.5

See Recommendations'93 R-2.5

R-2.5 Substituent Prefix Names Derived from Parent Hydrides

The presence of one or more free valence(s) derived from the loss of one or more hydrogen atoms from a parent hydride is denoted by suffixes such as "-yl", "-diyl", "-ylidene", "-triyl", "-ylidyne". Monovalent -yl Divalent -diyl -ylidene Trivalent -triyl -ylidyne -ylylidene Tetravalent -tetrayl -ylylidyne -diylidene -diylylidene etc. etc.

Note: In these recommendations, the suffixes "-ylidene" and "-ylidyne" are used only to indicate the attachment of a substituent to a parent hydride or parent substituent by a double or triple bond, respectively. These suffixes are used according to two methods as follows: (a) The suffixes "-yl", "-ylidene", and "-ylidyne" replace the ending "-ane" of the parent hydride name. The atom with the free valence terminates the chain and always has the locant "1", which is omitted from the name. This method is recommended only for saturated acyclic and monocyclic hydrocarbon substituent groups and for the mononuclear parent hydrides of silicon, germanium, tin, lead, and boron.

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(b) More general method. Any of these suffixes may be added to the name of the parent hydride with elision of a terminal "e", if present, before suffixes beginning with "y". The atoms with free valences are given numbers as low as is consistent with any established numbering of the parent hydride ; except for the suffix "-ylidyne", the locant number "1" must always be cited.
Examples to R-2.5

Isopropylidene (when unsubstituted)

19

The contracted names adamantyl, naphthyl, anthryl, phenanthryl (R-9.1, Table 22) and furyl, pyridyl, isoquinolyl, quinolyl, piperidyl (R-9.1, Table 25) are retained. The trivial names vinyl, allyl, and phenyl (R-9.1, Table 19(b)) and thienyl, furfuryl, and thenyl (see R-9.1, Table 25) are retained for use with no limitation on substitution; other trivial names are retained but only with limited or no substitution (see R-9.1, Table 19(b)).

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