Chemical Sciences Organic Chemistry Alkenes and Alkynes Introduction to the Alkenes An alkene is the simplest of the unsaturated

hydrocarbons, hydrocarbons which will react with hydrogen. Alkenes contain one or more reactive double bonds between carbon atoms, and are easily indicated by the symbol =. Since a double bond re uires two carbon atoms, the simplest alkene is C!"# or "!C=C"!, ethene. $he presence of a double bond is indicated by the change of ending from %ane to %ene. An older form of the name, ethylene, is used in chemical industry. Organic compounds which have a more comple& structure than simple alkanes are named as compounds which have been substituted. 'y substituted is meant replacement of a hydrogen by some other atom or group of atoms, or the insertion of a different type of chemical bond in the molecule. (ach of the different types of carbon%carbon bonds is designated by a change in the ending of the name of the compound. )or a carbon% carbon single bond, no ending change takes place because this is the normal structure of alkanes* the ending remains %ane. +eplacement of a single bond with a double bond, which re uires loss of a molecule of hydrogen, is indicated by changing the ending to %ene. $hus ethane, ",C%C",, can be converted to ethene, "!C=C"!. +eplacement of a single bond with a triple bond is less common. It is indicated by changing the ending to %yne. $hus ethane, ",C%C",, can be converted to ethyne, "CC", upon the loss of two molecules of hydrogen. Substitution can occur in whichever direction gives a useful name. $hus the compound C",Cl can be named either as a methane which has had a chlorine substituted upon it -name. chloromethane/ or as a chlorine which has had a methane substituted upon it -name. methyl chloride/. 'oth forms are correct, and both directions of substitution may be used in naming organic compounds. If and only if there is more than one possible location for the substitution, its location is specified by the number of the carbon at which the substitution takes place. $his numbering is arbitrarily from one upwards. )or simple compounds it begins at one end of the longest carbon chain, but for more comple& or ring structures the numbering is not necessarily obvious. International standardi0ing groups establish an agreed appropriate numbering pattern for more comple& structures. $his agreed numbering is given in reference works such as the +ing Inde&. Simple Substitution Simple substitution occurs when the substituent group replaces one hydrogen, or forms a single bond to the carbon chain -an e uivalent statement/. Some of the simple substituent groups and their effect on the name are shown in the following $able. $he e&amples are all for methyl but any alkyl -alkyl = substituent alkane/ compound is named in the analogous way* + denotes any alkyl group. 'oth directions of substitution can be used. $he forms indicated by asterisks in the $able are less common forms. $able. Simple Organic Substitution and 1omenclature

Compound 1ame 1ame -Substitution on Alkyl/ -Substitution by Alkyl/ +Cl chloromethane methyl chloride +'r bromomethane methyl bromide +I iodomethane methyl iodide +O" hydro&omethane2 methyl alcohol -methanol/ +1"! aminomethane2 methyl amine 3hen two or more different substituents appear on the same chain, they are named in alphabetical order. 3hen two or more of the same substituent appear in the same chain, the numberof substituents is indicated by a numerical prefi& -di, tri, tetra, .../. )or e&ample, butene has one double bond while butadiene has two. Copyright 4556 7ames A. 8lambeck -7im.8lambeck9ualberta.ca/. :pdated 7uly 4, 4556 ;p. $he location of the double bond is unambiguous in propene -also known as propylene/, but two butenes are possible. $hese two isomers are positional isomers. $hey have been called n%butene, C"=C"C"!C",, and isobutene, ",C%C"=C"C",, but are more commonly and correctly called 4%butene and !%butene. $wo butadienes, which each contain two double bonds, are known also. 4,!%butadiene, "!C=C=C"C",, and 4,,%butadiene, "!C=C"C"=C"!. Alkenes are considerably more reactive than are alkanes, and the addition of reactants across the double bond is common. "ydrogen will add across the double bond, as will halogens and hydrogen halides. An o&idation of the double bond, with a strong o&idi0ing agent such as potassium permanganate, often leads to cleavage of the molecule at the double bond with formation of carbo&ylic acids, which will be taken up in later sections, on both fragments. Cycloalkenes, like cycloalkanes, are possible and their reactivities are very similar to those of the straight% chain alkenes. Cycloalkenes are named in the same manner as cycloalkanes. Only the ending of the name is changed, to %ene. $he position is designated by a numeric prefi& only when necessary, which it would not be in a compound such as cyclohe&ene. Only positional isomers are possible for alkanes, but an additional form of isomers, geometric isomers, is possible for alkenes and other similar molecules. <eometric isomers in organic compounds arise because rotation about a single carbon%carbon bond is possible but rotation around a double carbon%carbon bond is not. $hus the distinction between two isomers of !%butene is real. $he compound with both methyl groups on the same -cis/ side of the double bond is called cis%!%butene, while the compound with the two methyl groups across -trans/ the double bond is called trans%!%butene. $he other positional isomer of butene, 4%butene, has no geometric isomers because both methyl groups are on the same carbon. One geometric isomer cannot be converted into the other without breaking the double bond.