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20.07 Alkenes and Alkynes

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    Learning Objectives

    • To name alkenes given formulas.
    • Name alkynes given formulas.

    Alkenes

    As noted before, alkenes are hydrocarbons with carbon-to-carbon double bonds (R2C=CR2) and alkynes are hydrocarbons with carbon-to-carbon triple bonds (R–C≡C–R). Collectively, they are called unsaturated hydrocarbons because they have fewer hydrogen atoms than does an alkane with the same number of carbon atoms, as is indicated in the following general formulas:

    unsaturated.jpg

    Some representative alkenes—their names, structures, and physical properties—are given in Table \(\PageIndex{1}\).

    Table \(\PageIndex{1}\): Physical Properties of Some Selected Alkenes
    IUPAC Name Molecular Formula Condensed Structural Formula Melting Point (°C) Boiling Point (°C)
    ethene C2H4 CH2=CH2 –169 –104
    propene C3H6 CH2=CHCH3 –185 –47
    1-butene C4H8 CH2=CHCH2CH3 –185 –6
    1-pentene C5H10 CH2=CH(CH2)2CH3 –138 30
    1-hexene C6H12 CH2=CH(CH2)3CH3 –140 63
    1-heptene C7H14 CH2=CH(CH2)4CH3 –119 94
    1-octene C8H16 CH2=CH(CH2)5CH3 –102 121

    We used only condensed structural formulas in Table \(\PageIndex{1}\). Thus, CH2=CH2 stands for

    CH2=CH2.jpg

    The double bond is shared by the two carbons and does not involve the hydrogen atoms, although the condensed formula does not make this point obvious. Note that the molecular formula for ethene is C2H4, whereas that for ethane is C2H6.

    The first two alkenes in Table \(\PageIndex{1}\), ethene and propene, are most often called by their common names—ethylene and propylene, respectively (Figure \(\PageIndex{1}\)). Ethylene is a major commercial chemical. The US chemical industry produces about 25 billion kilograms of ethylene annually, more than any other synthetic organic chemical. More than half of this ethylene goes into the manufacture of polyethylene, one of the most familiar plastics. Propylene is also an important industrial chemical. It is converted to plastics, isopropyl alcohol, and a variety of other products.

    clipboard_ec3d9f64616bb9f22536446653586c400.png
    Figure \(\PageIndex{1}\): Ethene and Propene. The ball-and-spring models of ethene/ethylene (a) and propene/propylene (b) show their respective shapes, especially bond angles.

    Although there is only one alkene with the formula C2H4 (ethene) and only one with the formula C3H6 (propene), there are several alkenes with the formula C4H8.

    Here are some basic rules for naming alkenes from the International Union of Pure and Applied Chemistry (IUPAC):

    1. The longest chain of carbon atoms containing the double bond is considered the parent chain. It is named using the same stem as the alkane having the same number of carbon atoms but ends in -ene to identify it as an alkene. Thus the compound CH2=CHCH3 is propene.
    2. If there are four or more carbon atoms in a chain, we must indicate the position of the double bond. The carbons atoms are numbered so that the first of the two that are doubly bonded is given the lower of the two possible numbers.The compound CH3CH=CHCH2CH3, for example, has the double bond between the second and third carbon atoms. Its name is 2-pentene (not 3-pentene).
    3. Substituent groups are named as with alkanes, and their position is indicated by a number. Thus,
      naming.jpg

      is 5-methyl-2-hexene. Note that the numbering of the parent chain is always done in such a way as to give the double bond the lowest number, even if that causes a substituent to have a higher number. The double bond always has priority in numbering.

    4. If there is more than one double bond in an alkene, all of the bonds should be numbered in the name of the molecule - even terminal double bonds. The numbers should go from lowest to highest, and be separated from one another by a comma. The IUPAC numerical prefixes are used to indicate the number of double bonds.

      • octa-2,4-diene: \(\ce{CH3CH=CHCH=CHCH2CH2CH3}\)
      • deca-1,5-diene: \(\ce{CH2=CHCH2CH2CH=CHCH2CH2CH2CH3}\)

     

    Example \(\PageIndex{1}\)

    Name each compound.

    1. clipboard_e7708582d323c1972aea3cc2187fe608f.png
     
    1. clipboard_e00994ff317f7e74395cf8325ff339f6e.png

    SOLUTION

    1. The longest chain containing the double bond has five carbon atoms, so the compound is a pentene (rule 1). To give the first carbon atom of the double bond the lowest number (rule 2), we number from the left, so the compound is a 2-pentene. There is a methyl group on the fourth carbon atom (rule 3), so the compound’s name is 4-methyl-2-pentene.
    2. The longest chain containing the double bond has five carbon atoms, so the parent compound is a pentene (rule 1). To give the first carbon atom of the double bond the lowest number (rule 2), we number from the left, so the compound is a 2-pentene. There is a methyl group on the third carbon atom (rule 3), so the compound’s name is 3-methyl-2-pentene.

    Exercise \(\PageIndex{1}\)

    Name each compound.

    1. CH3CH2CH2CH2CH2CH=CHCH3

       

    2. clipboard_e3b41ac618143b7d43fd524f13c91bcf2.png

     

    Alkynes

    The simplest alkyne—a hydrocarbon with carbon-to-carbon triple bond—has the molecular formula C2H2 and is known by its common name—acetylene (Figure \(\PageIndex{1}\)). Its structure is H–C≡C–H.

    13.6.1.jpg
    Figure \(\PageIndex{1}\): Ball-and-Spring Model of Acetylene. Acetylene (ethyne) is the simplest member of the alkyne family.

    Acetylene is used in oxyacetylene torches for cutting and welding metals. The flame from such a torch can be very hot. Most acetylene, however, is converted to chemical intermediates that are used to make vinyl and acrylic plastics, fibers, resins, and a variety of other products.

    Alkynes are similar to alkenes in both physical and chemical properties. For example, alkynes undergo many of the typical addition reactions of alkenes. The International Union of Pure and Applied Chemistry (IUPAC) names for alkynes parallel those of alkenes, except that the family ending is -yne rather than -ene. The IUPAC name for acetylene is ethyne. The names of other alkynes are illustrated in the following exercises.

    Concept Review Exercises

    1. Briefly identify the important distinctions between a saturated hydrocarbon and an unsaturated hydrocarbon.

    2. Briefly identify the important distinctions between an alkene and an alkane.

    3. Classify each compound as saturated or unsaturated. Identify each as an alkane, an alkene, or an alkyne.

      1. CR 3a.jpg
      2.                                            CH3CH2C≡CCH3
      3. CR 3c.jpg
    4. Briefly identify the important differences between an alkene and an alkyne. How are they similar?
    5. The alkene (CH3)2CHCH2CH=CH2 is named 4-methyl-1-pentene. What is the name of (CH3)2CHCH2C≡CH?
    6. Name each alkyne.
      1. CH3CH2CH2C≡CH
      2. CH3CH2CH2C≡CCH3

    Answers

    1. Unsaturated hydrocarbons have double or triple bonds and are quite reactive; saturated hydrocarbons have only single bonds and are rather unreactive.

    2. An alkene has a double bond; an alkane has single bonds only.

    3.  

      1. saturated; alkane
      2. unsaturated; alkyne
      3. unsaturated; alkene
    4. Alkenes have double bonds; alkynes have triple bonds. Both undergo addition reactions.
    5. 4-methyl-1-pentyne
      1. 1-pentyne
      2. 2-hexyne

    Key Takeaway

    • Alkenes are hydrocarbons with a carbon-to-carbon double bond.
    • Alkynes are hydrocarbons with carbon-to-carbon triple bonds and properties much like those of alkenes

    Exercises

    1. Name each compound according to the IUPAC system.

      1. Ex 3a.jpg
      2. Ex 3b.jpg
      3. Ex 3c.jpg

    2. Name each alkyne.

      1. CH3CH2CH2C≡CH
      2. CH3CH2CH2C≡CCH3

    Answers

      1. 2-methyl-1-pentene
      2. 2-methyl-2-pentene
      3. 2,5-dimethyl-2-hexene
      1. 1-pentyne
      2. 2-hexyne
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