Chapter 4: Alkenes and Alkynes. Degree of unsaturation

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1 hapter 4: Alkenes and Alkynes Unsaturated ydrocarbon: ontains one or more carbon-carbon double or triple bonds or benzene-like rings. Alkene: contains a carbon-carbon double bond and has the general formula n 2n. Alkyne: contains a carbon-carbon triple bond and has the general formula n 2n-2. Arene: benzene and its derivatives Note that benzene is a great example of resonance The reactivity of arenes is very different than the reactivity of alkenes. We do not study benzene and its derivatives until hapter 9. owever, we need know to the structure of the benzene molecule. And we need to know how to name a compound when benzene is used as a branch. When benzene is a branch, it is called the phenyl group. (benzyl has another meaning that we ll examine later.) The phenyl group does not react like an alkene or an alkyne (nor does benzene itself). Degree of unsaturation It can be helpful sometimes to compare an alkene, alkyne or cyclic hydrocarbon to an alkane with the same number of carbons. An unsaturated hydrocarbon will have fewer hydrogen atoms than a saturated hydrocarbon because it has double or triple bonds. Every extra carbon-carbon bond (double and triple bonds) or ring that an unsaturated hydrocarbon has is called a degree of unsaturation. Degrees of unsaturation can be determined by comparing the number of hydrogen atoms in a normal alkane (2n + 2) to the number of hydrogen atoms in the unsaturated compound. Subtract the number of hydrogens of the unsaturated compound from the number of hydrogens in the saturated compound and divide by two. Examples propene carbon alkane has 8 hydrogens, but propene has 6 hydrogens; therefore it has 1 degree of unsaturation. 1,3-hexadiene 2 6-carbon alkane has 14 hydrogens, but 1,3- hexadiene has 10 hydrogens; therefore it has 2 degrees of unsaturation. but-3-en-1-yne carbon alkane has 10 hydrogens, however, but-3-en-1-yne has 4 hydrogens; therefore, it has 3 degrees of unsaturation. 1

2 1,4-cyclohexadiene 2 2 Structure of Alkenes The two carbon atoms in a double bond and the four atoms bonded to them lie in a plane, with bond angles of approximately 120. Note the steric effect of the double bond and the methyl group. 6-carbon alkane has 14 hydrogens, but 1,4- cyclohexadiene has 8 hydrogens; therefore it has 3 degrees of unsaturation. Note the formation of the ring counts as a degree of unsaturation, even though cyclic alkanes aren t usually considered to be unsaturated hydrocarbons. According to the orbital overlap model, a double bond consists of one bond formed by the overlap of sp 2 hybrid orbitals and one bond formed by overlap of parallel 2p orbitals. Rotating by 90 breaks the pi bond. Thus, alkenes can have different geometric isomers, since there can be no rotation about the double bond. Geometrical Isomers of Alkenes The geometric isomers of an alkene have different chemical and physical properties. Because of steric strain between alkyl substituents of the same side of the double bond, a trans alkene is more stable than an isomeric cis alkene. The cis-trans system: configuration is determined by the orientation of atoms of the main chain. The cis isomer extends the carbon chain on the same side of the double bond. The trans isomer extends the carbon chain on different sides of the double bond. 2

3 Nomenclature of Alkenes IUPA nomenclature of alkenes Use the infix -en- to show the presence of a carboncarbon double bond. Number the parent chain to give the 1 st carbon of the double bond the lower number. Follow IUPA rules for numbering and naming substituents. For a cycloalkene, the numbering of the atoms of the ring the must begin with the two carbons of the double bond. Examples of IUPA alkene nomenclature 1-exene 2,3-Dimethylcyclohexene ommon nomenclature of alkenes Some alkenes, particularly low-molecular-weight ones, are known almost exclusively by their common names. E, Z onfigurations An alternative method to name geometric isomers is the E, Z method. To assign an E or Z configuration, first assign a priority to the substituents on each carbon of the double bond. If the groups of higher priority are on the same side of the double bond, the configuration is Z (German: zusammen, together). If the groups of higher priority are on opposite sides of the double bond, the configuration is E (German: entgegen, opposite). Priority rules (ahn-ingold-prelog rules) 1. Priority is based on atomic number; the higher the atomic number, the higher the priority. 3. Atoms participating in a double or triple bond are considered to be bonded to an equivalent number of similar atoms by single bonds. 2. If priority cannot be assigned on the basis of the atoms bonded directly to the double bond, look to the next set of atoms; priority is assigned at the first point of difference. 3

4 Examples: 1-bromo-1-chloropropene Examples: 2-chloro-2-pentene On the left side of the double bond, bromo has higher priority than chloro On the right side of the double bond, methyl has higher priority than hydrogen. igher priority is on the same side as the other higher priority; therefore, this compound is (Z)-1-bromo-1- chloropropene. On the left side of the double bond, chlorine has higher priority than methyl On the right side of the double bond, ethyl has higher priority than hydrogen. igher priority is opposite the other higher priority; therefore, this compound is (E)-2-chloro-2-pentene. Examples: 1-chloro-2,3-dimethyl-2-pentene Examples: 3,4-dimethyl-2-pentene On the left side of the double bond, chloromethyl has On the right side of the double bond, ethyl has igher priority is opposite the other higher priority; therefore, this compound is (E)-1-chloro-2,3-dimethyl- 2-pentene. On the left side of the double bond, methyl has higher priority than hydrogen On the right side of the double bond, isopropyl has igher priority is on same side as the other higher priority; therefore, this compound is (Z)-3,4-dimethyl- 2-pentene. Examples: 2,3,4-trimethyl-3-heptene On the left side of the double bond, propyl has On the right side of the double bond, isopropyl has igher priority is opposite the other higher priority; therefore, this compound is (E)-2,3,4-trimethyl-3- heptene. Other Instances of Geometric Isomerism ycloalkenes The configuration of the double bond in cyclopropene through cycloheptene must be cis. These rings are not large enough to accommodate a trans double bond. yclooctene is the smallest cycloalkene that can accommodate a trans double bond. 4

5 Dienes, trienes, and polyenes For an alkene with n carbon-carbon double bonds, each of which can show cis-trans isomerism, 2 n cistrans isomers are possible. onsider 2,4-heptadiene; it has four cis-trans isomers, two of which are drawn here below. onjugated Alkenes onjugated hydrocarbons have multiple double bonds that alternate with single bonds within a chain or a ring. 1,3-pentadiene is a conjugated alkene; whereas, 1,2-pentadiene or 1,4-pentadiene are not. 1,3-pentadiene (conjugated!) 1,2-pentadiene (an allene) 1,4-pentadiene onjugated alkenes have lower energies than nonconjugated alkenes. -electrons in bonds can be spread across more than two atoms. when electrons are less constrained, their energy decreases. For example, the p orbitals on carbons 1, 2, 3 and 4 of 1,3-pentadiene all overlap to create orbitals that involve all 4 of the first atoms in the hydrocarbon chain. onjugated systems have even numbers ( 4) of consecutive sp 2 atoms in its structure. Reactions with conjugated alkenes can give surprising results because the resonance structures with which conjugated systems can participate. Note the positive charge in the conjugated system is widely distributed because of resonance. 4 consecutive p orbitals can overlap to make conjugated system. p orbitals of neighboring pi bonds are perpendicular (can t make conjugated system). p orbitals on carbons 2 and 4 can t overlap (can t make conjugated system). 28 Natural Products The biochemical processes of organisms have strong (if not exclusive) preference for one geometric isomer over another. Vitamin A Vitamin A has five - double bonds. Four of the five can show cis-trans isomerism. Vitamin A is the all-trans isomer. O O O Fats Omega-3 fats have all cis configurations. Trans fats have all trans configurations. Trans fats are substituted for natural fats because they are cheaper to make. Saturated fats have no double bonds. Saturated fats are less expensive than trans fats. -linolenic acid (part of an omega-3 fat) O O elaidic acid (part of a trans fat) O stearic acid (part of a saturated fat) 5

6 Structure of Alkynes The functional group of an alkyne is a carboncarbon triple bond. A triple bond consists of: One bond formed by the overlap of sp hybrid orbitals. Two bonds formed by the overlap of sets of parallel 2p orbitals. Note the two bonds in an alkyne are perpendicular to each other. Nomenclature of Alkynes IUPA nomenclature of alkynes Use the infix -yn to show the presence of a carboncarbon triple bond. Number the parent chain to give the 1 st carbon of the triple bond the lower number. Follow IUPA rules for numbering and naming substituents. Physical Properties of Alkene and Alkynes Alkenes and alkynes are nonpolar compounds. The only attractive forces between their molecules are dispersion forces. The physical properties of alkenes and alkynes are similar to those of alkanes of similar carbon skeletons. Those that are liquid at room temperature are less dense than water (1.0 g/ml). They dissolve in each other and in nonpolar organic solvents. They are insoluble in water. The Peculiar Acidity of Terminal Alkynes One of the major differences between the chemistry of alkynes, relative to alkenes is that the hydrogen atom of a terminal alkyne is sufficiently acidic (pk a = 25) that it can be removed by a strong base such as sodium amide, NaN 2, to give an alkyne anion. The R : ion is also called an acetylide ion. Because water (pk a 15.7) is a stronger acid than acetylene or a terminal alkyne, hydroxide ion is not a strong enough base for an acid-base reaction with a terminal alkyne. 6

7 The pk a values for alkane and alkene hydrogens are so large that no base is strong enough to remove a hydrogen from either of these classes of compounds. Q: Why are terminal alkynes so acidic compared to alkenes and alkanes? A: Because the acetylide anion is a relatively stable ion. The lone pair of electrons of an alkane anion lies in an sp 3 hybrid orbital, which has 25% s character. For an alkene anion (also known as a vinyl anion), the lone pair lies in an sp 2 hybrid orbital, which has 33% s character. For an acetylide anion, the lone pair lies in an sp hybrid orbital, which has 50% s character. The greater the s character of the orbital bearing the negative charge, the greater the stability of the anion. The electron cloud of the lone pair gets closer to the nucleus and therefore has lower (more attractive) energy. Therefore, a terminal alkyne anion is the most stable of the series of hydrocarbon anions; and thus, a terminal alkyne is the most acidic. 7

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