ACD/Name

Acyclic Hydrocarbons

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 A-31.3 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

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)
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

Next:
Bivalent and Multivalent Radicals

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This HTML reproduction of Sections A, B and C of IUPAC "Blue Book" is as close as possible to the published version [see Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H, Pergamon Press, Oxford, 1979. Copyright 1979 IUPAC.] If you need to cite these rules please quote this reference as their source.

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