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 "al"ane". Examples of names# n $ total number of carbon atoms! n % &ethane ' Ethane ) *ropane + ,utane - *entane . Hexane / Heptane 0 1ctane 2 Nonane %3 (ecane %% 4ndecane %' (odecane %) Tridecane %+ Tetradecane %- *entadecane %. Hexadecane %/ Heptadecane %0 1ctadecane %2 Nonadecane '3 5cosane '% Henicosane n '' (ocosane ') Tricosane '+ Tetracosane '- *entacosane '. Hexacosane '/ Heptacosane '0 1ctacosane '2 Nonacosane )3 Triacontane )% Hentriacontane )' (otriacontane )) Tritriacontane +3 Tetracontane -3 *entacontane .3 Hexacontane /3 Heptacontane 03 1ctacontane 23 Nonacontane %33 Hectane %)' (otriacontahectane

1.2 - 4ni6alent radicals deri6ed from saturated unbranched acyclic hydrocarbons by remo6al 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 6alence is numbered as %. As a class, these radicals are called normal, or unbranched chain, al"yls.
Examples to Rule A-1.2

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# 5sobutane 5sopentane Neopentane 5sohexane 2.2 - The longest chain is numbered from one end to the other by Arabic numerals, the direction being so chosen as to gi6e the lowest numbers possible to the side chains. 7hen 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 irrespecti6e of the nature of the substituents.
Examples to Rule A-2.2

2.25 - 4ni6alent branched radicals deri6ed from al"anes are named by prefixing the designation of the side chains to the name of the unbranched al"yl radical possessing the longest possible chain starting from the carbon atom with the free 6alence, the said atom being numbered as %.
Examples to Rule A-2.25

%-&ethylpentyl '-&ethylpentyl --&ethylhexyl The following names may be used for the unsubstituted radicals only# 5sopropyl 5sobutyl sec-,utyl

tert-,utyl

5sopentyl

Neopentyl

tert-*entyl

5sohexyl 2.3 - 5f 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 alphabeti8ed and the multiplying prefixes are then inserted.
Examples to Rule A-2.3(i)

ethyl is cited before methyl, thus +-Ethyl-),)-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 alphabeti8ed under "d", thus /- %,'-(imethylpentyl!---ethyltridecane (iii) 5n cases where names of complex radicals are composed of identical words, priority for citation is gi6en 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 - 5f two or more side chains are in e9ui6alent 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! 4se of parentheses and unprimed numbers# -,--,is %,%-dimethylpropyl!-'-methyldecane

b! 4se of primes# -,--,is-%:,%:-dimethylpropyl-'-methyldecane

a! 4se of parentheses and unprimed numbers# /- %,%-(imethylbutyl!-/- %,%-dimethylpentyl!tridecane b! 4se of primes# /-%:,%:-(imethylbutyl-/-%",%"-dimethylpentyltridecane 2. - 5f chains of e9ual 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 ha6e the lowest-numbered locants.

Example to Rule A-2.6(b)

c! The chain ha6ing the greatest number of carbon atoms in the smaller side chains.
Example to Rule A-2.6(c)

d! The chain ha6ing the least branched side chains.

Example to Rule A-2.6(d)

Rule A-3. Unsaturated Compounds and Univalent Radicals

3.1 - 4nsaturated unbranched acyclic hydrocarbons ha6ing one double bond are named by replacing the ending "-ane" of the name of the corresponding saturated hydrocarbon with the ending "-ene". 5f there are two or more double bonds, the ending will be "adiene", "-atriene", etc. The generic names of these hydrocarbons branched or unbranched! are "al"ene", "al"adiene", "al"atriene", etc. The chain is so numbered as to gi6e the lowest possible numbers to the double bonds. 7hen, 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 <ules A-)%.) and A-)%.+!.
Examples to Rule A-3.1

'-Hexene %,+-Hexadiene The following non-systematic names are retained# Ethylene Allene 3.2 - 4nsaturated unbranched acyclic hydrocarbons ha6ing one triple bond are named by replacing the ending "-ane" of the name of the corresponding saturated hydrocarbon with the ending "-yne". 5f there are two or more triple bonds, the ending will be "-adiyne", "atriyne", etc. The generic names of these hydrocarbons branched or unbranched! are

"al"yne", "al"adiyne", "al"atriyne", etcThe chain is so numbered as to gi6e the lowest possible numbers to the triple bonds. 1nly the lower locant for a triple bond is cited in the name of a compound. The name "acetylene" for is retained.

3.3 - 4nsaturated unbranched acyclic hydrocarbons ha6ing 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 gi6en to double and triple bonds e6en though this may at times gi6e "-yne" a lower number than "-ene". 7hen there is a choice in numbering, the double bonds are gi6en the lowest numbers.
Examples to Rule A-3.3

%,)-Hexadien---yne )-*enten-%-yne %-*enten-+-yne 3.4 - 4nsaturated branched acyclic hydrocarbons are named as deri6ati6es of the unbranched hydrocarbons which contain the maximum number of double and triple bonds. 5f there are two or more chains competing for selection as the chain with the maximum number of unsaturated bonds, then the choice goes to %! that one with the greatest number of carbon atoms; '! the number of carbon atoms being e9ual, that one containing the maximum number of double bonds. 5n other respects, the same principles apply as for naming saturated branched acyclic hydrocarbons. The chain is so numbered as to gi6e the lowest possible numbers to double and triple bonds in accordance with <ule A-).).
Examples to Rule A-3.4

The following name is retained for the unsubstituted compound only#

3.5 - The names of uni6alent radicals deri6ed from unsaturated acyclic hydrocarbons ha6e the endings "-enyl", "-ynyl", "-dienyl", etc., the positions of the double and triple bonds being indicated where necessary. The carbon atom with the free 6alence is numbered as %.
Examples to Rule A-3.5

Ethynyl '-*ropynyl %-*ropenyl '-,utenyl %,)-,utadienyl '-*entenyl '-*enten-+-ynyl Exceptions# The following names are retained for unsubstituted radical only!# =inyl for ethenyl! Allyl for '-propenyl! 5sopropenyl for %-methyl6inyl! 3. - 7hen there is a choice for the fundamental chain of a radical, that chain is selected which contains %! the maximum number of double and triple bonds; '! the largest number of carbon atoms; and )! the largest number of double bonds.
Examples to Rule A-3.6

Rule A-4. Bivalent and !ultivalent Radicals

4.1 - ,i6alent and tri6alent radicals deri6ed from uni6alent acyclic hydrocarbon radicals whose authori8ed names end in "-yl" by remo6al of one or two hydrogen atoms from the carbon atom with the free 6alences are named by adding "-idene" or "-idyne", respecti6ely, to the name of the corresponding uni6alent radical. The carbon atom with the free 6alence is numbered as %. The name "methylene" is retained for the radical
Examples to Rule A-4.1

&ethylidene Ethylidene Ethylidyne =inylidene 5sopropylidene 4.2 - The names of bi6alent radicals deri6ed from normal al"anes by remo6al 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

*entamethylene Hexamethylene Names of the substituted bi6alent radicals are deri6ed in accordance with <ules A-'.' and A-'.'-.
Example to Rule A-4.2a

The following name is retained#

4.3 - ,i6alent radicals similarly deri6ed from unbranched al"enes, al"adienes, al"ynes, etc., by remo6ing 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 bi6alent radicals are deri6ed in accordance with <ule A-).+.
Example to Rule A-4.3

4.4 - Tri6alent, 9uadri6alent and higher-6alent acyclic hydrocarbon radicals of two or more carbon atoms with the free 6alences at each end of a chain are named by adding to the hydrocarbon name the terminations "-yl" for a single free 6alence, "-ylidene" for a double, and "-ylidyne" for a triple free 6alence on the same atom the final "e" in the name of the hydrocarbon is elided when followed by a suffix beginning with "-yl"!. 5f 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

,utanediylidene ,utanediylidyne %-*ropanyl-)-ylidene *ropadienediylidene '-*entenediylidyne %-,utanyliden-+-ylidyne 4.5 - &ulti6alent radicals containing three or more carbon atoms with free 6alences at each end of a chain and additional free 6alences 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

"arent #$drides R-2.5 Substituent "re%i& 'ames (erived %rom "arent #$drides
The presence of one or more free 6alence s! deri6ed from the loss of one or more hydrogen atoms from a parent hydride is denoted by suffixes such as "-yl", "-diyl", "ylidene", "-triyl", "-ylidyne". &ono6alent -yl (i6alent -diyl -ylidene Tri6alent -triyl -ylidyne -ylylidene Tetra6alent -tetrayl -ylylidyne -diylidene -diylylidene etc. etc.

Note: 5n 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, respecti6ely. 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 6alence terminates the chain and always has the locant "%", 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. b! ore 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 6alences are gi6en numbers as low as is consistent with any established numbering of the parent hydride ; except for the suffix "-ylidyne", the locant number "%" must always be cited.
Examples to R-2.5

5sopropylidene when unsubstituted!