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ChemWiki: The Dynamic Chemistry Hypertext > Core > Organic Chemistry > Hydrocarbons > Alkenes > Nomenclature of Alkenes

Nomenclature of Alkenes

Alkenes contain carbon-carbon double bonds and are unsaturated hydrocarbons with the molecular formula is CnH2n. This is also the same molecular formula as cycloalkanes. Alkenes are named by dropping the -ane ending of the parent and adding -ene.


Alkenes and alkynes are hydrocarbons which respectively have carbon-carbon double bond and carbon-carbon triple bond functional groups. The molecular formulas of these unsaturated hydrocarbons reflect the multiple bonding of the functional groups:


Alkane CnH2n+2 This is the maximum H/C ratio for a given number of carbon atoms.
Alkene CnH2n Each double bond reduces the number of hydrogen atoms by 2.

The parent structure is the longest chain containing both carbon atoms of the double bond. The two carbon atoms of a double bond and the four atoms attached to them lie in a plane, with bond angles of approximately 120° A double bond consists of one sigma bond formed by overlap of sp2 hybrid orbitals and one pi bond formed by overlap of parallel 2 p orbitals


Figure 1: (a) The σ-bonded framework is formed by the overlap of two sets of singly occupied carbon sp2 hybrid orbitals and four singly occupied hydrogen 1s orbitals to form electron-pair bonds. This uses 10 of the 12 valence electrons to form a total of five σ bonds (four C–H bonds and one C–C bond). (b) One singly occupied unhybridized 2pz orbital remains on each carbon atom to form a carbon–carbon π bond. (Note: by convention, in planar molecules the axis perpendicular to the molecular plane is the z-axis.)

The molecular formula of a hydrocarbon provides information about the possible structural types it may represent. For example, consider compounds having the formula C5H8. The formula of the five-carbon alkane pentane is C5H12 so the difference in hydrogen content is 4. This difference suggests such compounds may have a triple bond, two double bonds, a ring plus a double bond, or two rings. Some examples are shown here, and there are at least fourteen others!

IUPAC Rules for Alkene and Cycloalkene Nomenclature

  1.  The ene suffix (ending) indicates an alkene or cycloalkene.
  2.  The longest chain chosen for the root name must include both carbon atoms of the double bond.
  3.  The root chain must be numbered from the end nearest a double bond carbon atom. If the double bond is in the center of the chain, the nearest substituent rule is used to determine the end where numbering starts.
  4.  The smaller of the two numbers designating the carbon atoms of the double bond is used as the double bond locator. If more than one double bond is present the compound is named as a diene, triene or equivalent prefix indicating the number of double bonds, and each double bond is assigned a locator number.
  5.  In cycloalkenes the double bond carbons are assigned ring locations #1 and #2. Which of the two is #1 may be determined by the nearest substituent rule.
  6.  Substituent groups containing double bonds are:

            H2C=CH–   Vinyl group
            H2C=CH–CH2   Allyl group


Example 1


In this diagram this is a cis conformation. It has both the substituents going upward. This molecule would be called (cis) 5-chloro-3-heptene.)

Trans would look like this

v. On the other hand if there are 3 or 4 non-hydrogen different atoms attached to the alkene then use the E, Z system.

E (entgegen) means the higher priority groups are opposite one another relative to the double bond.

Z (zusammen) means the higher priority groups are on the same side relative to the double bond.

(You could think of Z as Zame Zide to help memorize it.)

Example 2


In this example it is E-4-chloro-3-heptene. It is E because the Chlorine and the CH2CH3 are the two higher priorities and they are on opposite sides.  

 vi. A hydroxyl group gets precedence over th double bond. Therefore alkenes containing alchol groups are called alkenols. And the prefix becomes --enol. And this means that now the alcohol gets lowest priority over the alkene. 

vii. Lastly remember that alkene substituents are called alkenyl. Suffix --enyl.



Here is a chart containing the systemic name for the first twenty straight chain alkenes.

Name Molecular formula
Ethene C2H4
Propene C3H6
Butene C4H8
 Pentene  C5H10
 Hexene  C6H12
 Heptene  C7H14
 Octene  C8H16
 Nonene  C9H18
 Decene  C10H20
 Undecene  C11H22
 Dodecene  C12H24
 Tridecene  C13H26
 Tetradecene  C14H28
 Pentadecene  C15H30
 Hexadecene  C16H32
Heptadecene C17H34
 Octadecene  C18H36
 Nonadecene  C19H38
 Eicosene  C20H40

Did you notice how there is no methene? Because it is impossible for a carbon to have a double bond with nothing.

Geometric Isomers

Double bonds can exist as geometric isomers and these isomers are designated by using either the cis / trans designation or the modern E / Z designation.

cis Isomers

.The two largest groups are on the same side of the double bond.

trans Isomers

...The two largest groups are on opposite sides of the double bond.

E/Z nomenclature

E = entgegan ("trans") Z = zusamen ("cis")

Priority of groups is based on the atomic mass of attached atoms (not the size of the group). An atom attached by a multiple bond is counted once for each bond.

fluorine atom > isopropyl group > n-hexyl group

deuterium atom > hydrogen atom

-CH2-CH=CH2 > -CH2CH2CH3

Example 3

Try to name the following compounds using both conventions...

Common names

Remove the -ane suffix and add -ylene. There are a couple of unique ones like ethenyl's common name is vinyl and 2-propenyl's common name is allyl. That you should know are...

  • vinyl substituent H2C=CH-
  • allyl substituent H2C=CH-CH2-
  • allene molecule H2C=C=CH2
  • isoprene

Endocyclic Alkenes

Endocyclic double bonds have both carbons in the ring and exocyclic double bonds have only one carbon as part of the ring.


Cyclopentene is an example of an endocyclic double bond.

Methylenecylopentane is an example of an exocyclic double bond.

Name the following compounds...


1-methylcyclobutene. The methyl group places the double bond. It is correct to also name this compound as 1-methylcyclobut-1-ene.



 1-ethenylcyclohexene, the methyl group places the double bond. It is correct to also name this compound as 1-ethenylcyclohex-1-ene. A common name would be 1-vinylcyclohexene.


Try to draw structures for the following compounds...


  •  2-vinyl-1,3-cyclohexadiene



  1. Vollhardt, Peter, and Neil E. Schore. Organic Chemistry: Structure and Function. 5th Edition. New York: W. H. Freeman & Company, 2007.


Try to name the following compounds...


1-pentene or pent-1-ene



 2-ethyl-1-hexene or 2-ethylhex-1-ene

Try to draw structures for the following compounds...

  •  2-pentene


  •  3-heptene


b. Give the double bond the lowest possible numbers regardless of substituent placement.

 • Try to name the following compound...


• Try to draw a structure for the following compound...

4-methyl-2-pentene J

Name the following structures:

alkene problem 2.jpg

v. Draw (Z)-5-Chloro-3-ethly-4-hexen-2-ol.



I. trans-8-ethyl-3-undecene

II. E-5-bromo-4-chloro-7,7-dimethyl-4-undecene

III. Z-1,2-difluoro-cyclohexene

IV. 4-ethenylcyclohexanol.

V. alkene9.jpg


  • S. Devarajan (UCD)

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Last modified
11:45, 26 Feb 2016



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This material is based upon work supported by the National Science Foundation under Grant Numbers 1246120, 1525057, and 1413739.

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