Assistant Lecture Aayad Ammar

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1 Assistant Lecture Aayad Ammar Alkenes and Alkynes: Structure and Physical Properties Alkenes and alkynes are unsaturated hydrocarbons. The characteristic functional group of an alkene is the carbon-carbon double bond. The functional group that characterizes the alkynes is the carbon-carbon triple bond. The following general formulas compare the structures of alkanes, alkenes, and alkynes These compounds have the same number of carbon atoms but differ in the number of hydrogen atoms, a feature of all alkanes, alkenes, and alkynes that contain the same number of carbon atoms. Alkenes contain two fewer hydrogens than the corresponding alkanes, and alkynes contain two fewer hydrogens than the corresponding alkenes. In alkanes the four bonds to the central carbon have tetrahedral geometry.when carbon is bonded by one double bond and two single bonds, as in ethene(an alkene), the molecule is planar, because all atoms lie in a single plane. Each bond angle is approximately 120_. When two carbon atoms are bonded by a triple bond, as in ethyne (an alkyne), each bond angle is 180_. Thus, the molecule is linear, and all atoms are positioned in a straight line (Figure 12.2). The physical properties of alkenes, alkynes, and aromatic compounds are very similar to those of alkanes. They are nonpolar. As a result of the like dissolves like rule, they are not soluble in water but are very soluble in nonpolar solvents such as other hydrocarbons. They also have relatively low boiling points and melting points. Alkenes and Alkynes: Nomenclature To determine the name of an alkene or alkyne using the I.U.P.A.C. Nomenclature System, use the following simple rules: Name the parent compound using the longest continuous carbon chain containing the double bond (alkenes) or triple bond (alkynes). Replace the -ane ending of the alkane with the -ene ending for an alkene or the -yne ending for an alkyne. For example:

2 Number the chain to give the lowest number for the first of the two carbons containing the double bond or triple bond. For example: Name and number all groups bonded to the parent alkene or alkyne, and place the name and number in front of the name of the parent compound. Remember that with alkenes and alkynes the double or triple bond takes precedence over a halogen or alkyl group, as shown in the following examples:

3 Alkenes having more than one double bond are called alkadienes (two double bonds) or alkatrienes (three double bonds), as seen in these examples Draw a complete structural formula for each of the following compounds: a. 1-Bromo-3-hexyne b. 2-Butyne c. Dichloroethyne d. 9-Iodo-1-nonyne Name the following compounds using the I.U.P.A.C. Nomenclature System:

4 Geometric Isomers: A Consequence of Unsaturation The carbon-carbon double bond is rigid because of the shapes of the orbitals involved in its formation. The electrons of one of the two carbon-carbon bonds lie in a line between the two nuclei. This is called a sigma bond. The second bond is formed between two p orbital electrons and is called a pi bond. The two electrons of the bond lie in the region above and below the two carbon atoms as shown in the following diagram. Rotation around the double bond is restricted because the bond would have to be broken to allow rotation. Thus, the double bond is rigid., we observed that the rotation around the carbon-carbon bonds of cycloalkanes was restricted. The consequence of the absence of free rotation was the formation of geometric or cistrans isomers. The cis isomers of cycloalkanes had substituent groups on the same side of the ring (L., cis, on the same side ). The trans isomers of cycloalkanes had substituent groups located on opposite sides of the ring (L., trans, across from ).In the alkenes, geometric isomers differ from one another by the location of groups on the same or opposite sides of the double bond. Because the double bond of the alkenes is also rigid and there is no free rotation around it, geometric isomers are formed when there are two different groups on each of the carbon atoms attached by the double bond. If both groups are on the same side of the double bond, the molecule is a cis isomer. If the groups are on opposite sides of the double bond, the molecule is a trans isomer.consider the two isomers of 1,2-dichloroethene:

5 If one of the two carbon atoms of the double bond has two identical substituents, there are no cis-trans isomers for that molecule. Consider the example of 1,1- dichloroethene:

6

7 Reactions Involving Alkenes : Reactions of alkenes involve the carbon-carbon double bond. The key reaction of the double bond is the addition reaction. This involves the addition of two atoms or groups of atoms to a double bond. The major alkene addition reactions include addition of hydrogen (H 2 ), halogens (Cl 2 or Br 2 ), water (HOH), or hydrogen halides (HBr or HCl). A generalized addition reaction is: Hydrogenation: Addition of H 2 to an Alkene Hydrogenation is the addition of a molecule of hydrogen (H 2 ) to a carbon-carbon double bond to give an alkane. In this reaction the double bond is broken, and two new C H single bonds result. Platinum, palladium, or nickel is needed as a catalyst to speed up the reaction. Heat and/or pressure may also be required.

8 Hydrogenation is used in the food industry to produce margarine, which is a mixture of hydrogenated vegetable oils, Vegetable oils are unsaturated,that is, they contain

9 many double bonds and as a result have low melting points and are liquid at room temperature. The hydrogenation of these double bonds to single bonds increases the melting point of these oils and results in a fat,such as Crisco, that remains solid at room temperature. Through further processing they may be converted to margarine, such as corn oil or sunflower oil margarines. Halogenation: Addition of X 2 to an Alkene Chlorine (Cl 2 ) or bromine (Br 2 ) can be added to a double bond. This reaction, called halogenation, proceeds readily and does not require a catalyst:

10 Below we see an equation representing the bromination of 1-pentene. Notice that the solution of reactants is red because of the presence of bromine. However, the product is colorless This bromination reaction can be used to show the presence of double bonds in an organic compound. The reaction mixture is red because of the presence of dissolved bromine. If the red color is lost, the bromine has been consumed. Thus bromination has occurred, and the compound must have had a carbon-carbon double bond. The greater the amount of bromine that must be added to the reaction,the more unsaturated the compound is, that is, the greater the number of carbon-carbon double bonds. Hydration: Addition of H 2 O to an Alkene A water molecule can be added to an alkene. This reaction, termed hydration, requires a trace of acid as a catalyst. The product is an alcohol, as shown in the following reaction:

11 The following equation shows the hydration of ethene to produce ethanol With alkenes in which the groups attached to the two carbons of the double bond are different (unsymmetrical alkenes), two products are possible. For example: When hydration of an unsymmetrical alkene, such as propene, is carried out in the laboratory, one product (2-propanol) is favored over the other. The Russian chemist Vladimir Markovnikov studied many such reactions and came up with a rule that can be used to predict the major product of such a reaction Markovnikov s rule tells us that the carbon of the carbon-carbon double bond that originally has more hydrogen atoms receives the hydrogen atom being added to the double bond. The remaining carbon forms a bond with the OH. Simply stated, the rich get richer the carbon with the most hydrogens gets the new one as well. In the preceding example, carbon-1 has two C H bonds originally, and carbon-2 has only one. The major product, 2- propanol, results from the new C H bond forming on carbon-1 and the new C OH bond on carbon-2.addition of water to a double bond is a reaction that we find in several biochemical pathways. For instance, the citric acid cycle is a key metabolic pathway for the complete oxidation of the sugar glucose and the release of the majority of the energy used by the body. It is also the source of starting materials for the synthesis of the biological molecules needed for life. The next-to-last reaction in the citric acid cycle is the hydration of a molecule of fumarate to produce a molecule called malate.

12 Hydrohalogenation: Addition of HX to an Alkene A hydrogen halide (HBr, HCl, or HI) also can be added to an alkene. The product of this reaction, called hydrohalogenation, is an alkyl halide:

13 This reaction also follows Markovnikov s rule. That is, if HX is added to an unsymmetrical alkene, the hydrogen atom will be added preferentially to the carbon atom that originally had the most hydrogen atoms. Consider the following example

14 Addition Polymers of Alkenes : Polymers are macromolecules composed of repeating structural units called monomers. A polymer may be made up of several thousand monomers. Many commercially important plastics and fibers are addition polymers made from alkenes or substituted alkenes. They are called addition polymers because they are made by the sequential addition of the alkene monomer. The general formula for this addition reaction follows: The product of the reaction is generally represented in a simplified manner Polyethylene is a polymer made from the monomer ethylene (ethene): It is used to make bottles, injection-molded toys and housewares, and wire coverings.polypropylene is a plastic made from propylene (propene). It is used to make indoor-outdoor carpeting, packaging materials, toys, and housewares. When propylene polymerizes, a methyl group is located on every other carbon of the

15 main chain:

16 This document was created with Win2PDF available at The unregistered version of Win2PDF is for evaluation or non-commercial use only.

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