1) Systematic naming of alkanes 2) Alkenes 3) Alkynes 4) Aromatic compounds (benzene etc) 5) Hydrocarbon physical properties 6) Petroleum chemistry
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1 Chem 106 Tues ) Systematic naming of alkanes 2) Alkenes 3) Alkynes 4) Aromatic compounds (benzene etc) 5) ydrocarbon physical properties 6) Petroleum chemistry 1/25/2011 1
2 pencil : paper :: paint brush : 1. canvas painting 3. paint palette canvas painting paint palette 1/25/2011 2
3 ydrocarbons Alkanes all sp 3 carbons Cycloalkanes all sp 3 carbons in a ring Alkenes one (or more) C=C bond (sp 2 C) Alkynes one (or more) C C bond (sp C) C n 2n+2 C n 2n (one ring) C n 2n (one C=C) C n 2n-2 (one C C) 1/25/2011 3
4 Alkane names are based on length of longest chain Need to know C 1 C 10 names. not obvious need to learn if you don t know them 1/25/2011 4
5 M Systematic names of complex alkanes ( I.U.P.A.C. ) Substituents Parent chain location-numbersubstituentsparent 1/25/2011 5
6 Substituents are sometimes called radicals. They are molecules but with a atom removed to create an attachment point. methane methyl substituent (C 3 ) ethane ethyl substituent (C 3 C 2 ) 1/25/2011 6
7 Then substituents can be attached somewhere along a longer chain. 2-methyloctane 1/25/2011 7
8 Alkane systematic names (1) Find longest chain in molecule C 3 (2) Number the chain starting at end closest to any substituents. (3) Identify the number (di, tri, tetra etc) and type (methyl, ethyl, etc) of substituents. 3 C C C C C C C 3 2,2-dimethylhexane all sp 3 1/25/2011 8
9 flip 6 3 C C C C C C C 3 C 3 This is also 2,2-dimethylhexane. It has the same name, therefore it s the same molecule This is an isomer: It has a different NAME and structure. C 3 3 C C C C C C 3 1/25/ C 3 2,3-dimethylhexane
10 Structure name Name structure 3,3,4,4,5-pentamethyldecane 1/25/
11 Naming an alkane: What is the parent chain of the following compound? 1. hexane heptane octane nonane hexane heptane octane nonane 1/25/
12 What substituent is not present in the systematic name of the following compound? 1. methyl 2. ethyl 3. propyl methyl ethyl propyl 1/25/
13 Show 2,2,3-trimethylpentane in ACD ChemSketch and yperchem. 1/25/ Free download at
14 Cycloalkalkanes have formula C n 2n (one ring) cyclopropane C 2 2 C C 2 cyclohexane cycloheptane Largest known cycloalkane: Cyclodotetracontane (C ) 1/25/
15 Alkenes contain C=C bond (C n 2n ) C 3 3 C 3 C C 3 1/25/
16 Naming alkenes (1) Find longest chain containing BOT CARBONS of C=C. (2) Number the carbons starting at the end nearest C=C. (3) Locate the C=C along the chain using # of FIRST C=. 3 C C Main chain 5 C s Location of C=C 2-pentene Main chain contains C=C 1/25/
17 Some alkenes exist in cis- or trans- geometric isomers C 3 Same atoms or groups compare their positions on C=C. 3 C trans- trans-2-pentene cis- 3 C C 3 cis-2-pentene 1/25/
18 No C=C bonds contain π-bond that depends on parallel orientation of the 2 p-orbitals on bonded carbons. This prevents twisting around the bond. Therefore C=C bonds containing different atoms can exist as cis- or trans- isomers C 3 C l C l C l C l C l C l C l C l C 3 cis isomers trans isomers 1/25/
19 trans- 4,5- diethyl- 4-nonene C 3 3 C 4 5 C C 3 1/25/
20 Alkanes are referred to as saturated hydrocarbons. They have the maximum number of s for a given # of C s. Alkenes are unsaturated - they have fewer s. Unsaturated fats contain C=C bonds along the fatty acid chain. As found in nature, these are usually cis- because the C=C plays a structural role in lipid bilayers. 1/25/
21 polar Saturated fatty acid Lard is derived from cell membranes of animals. It is rich in saturated fatty acid components. The straight chains pack tightly into the cell s membrane bilayer. Crosssection through cell membrane as proper structure and function at 37 C. 1/25/
22 Plant cell membranes contain unsaturated fatty acids rich in cis-double bonds. These chains are kinked by the cis bond, resulting in disordered lipid bilayer that is more fluid. It remains flexible at low temperatures, which maintains the proper biological functions of the cell membrane. 1/25/
23 trans-double bonds in fats are man-made. They are created during partial hydrogenation reactions that adds 2 to C=C bonds using a metal catalyst. The trans-acid packs into membranes in a manner similar to saturated fats. This may be the basis of the unhealthy effects of fats containing lots of trans fatty acids. 1/25/
24 Alkynes contain a C C triple bond. Each sp-hybridized carbon contains two unhybridized p-orbitals The four p-orbitals combine to form two π-bonds. C C 1/25/
25 -C C- common name is acetylene ( ethyne is the systematic name, but is not used.) C 3 C 2 C C C 2 C 2 C methyl-3-octyne 8 C 3 C 3 Uses: acetylene is welding gas larger alkynes used as synthesis intermediates because the C C bond can be modified in many ways. Some natural molecules such as dynemicin an anticancer drug contain C C bonds. 1/25/
26 Alkynes are used in organic synthesis reactions to create specific organic molecules. 2-hexyne cannot be obtained from crude oil or other natural sources. 3 C C C + Base 3 C C C + Base acetylide ion C l 3 C C C C 2 C 2 C 3 3 C C C C 2 C 2 C 3 + Cl 2-hexyne Synthesis products are larger than feedstock hydrocarbons, they have specific structures, and they often have useful chemical or biological properties. 1/25/
27 Aromatic hydrocarbons 1/25/
28 Aromatic hydrocarbons contain one or more benzene rings. C C C C C C C C C C C C Benzene itself is C 6 6. It is a resonance hybrid of two equivalent forms. This leads to an unusually stable molecule. This is called an aromatic ring which refers to the special stability of 6 π-electrons in a ring of sp 2 -atoms. Sometimes written this way to emphasize bonding symmetry: or 1/25/
29 Enhanced stability of the aromatic ring is due to formation of a low-energy π-molecular orbital extending around the ring. 1/25/
30 C 3 C 3 C 3 C 3 C 3 C 3 C 3 Toluene (methylbenzene) ortho-xylene meta-xylene para-xylene 1/25/
31 Binding energy (kcal/mol)* Toluene (methylbenzene) is 28 kcal/mol more stable than the next-most stable C 7 8 isomer C 3 3 C C 2 2 C C 2 C 2 Not aromatic C 3 Toluene * calculated with PM3 semi-empirical method Aromatic There are >100 isomers of C 7 8! 1/25/
32 ydrocarbon properties Boiling points vs molar mass GC separation 1/25/
33 1/25/
34 igh molecular weight hydrocarbons - strong induced dipoles (van der waals forces) due to their large exposed surface area. 1/25/2011 decane 34
35 Gas chromatogram of C 1 -C 6 hydrocarbons Courtesy of R. Stolzberg 1/25/
36 Courtesy of R. Stolzberg 1/25/
37 Courtesy of R. Stolzberg 1/25/
38 Distillation Courtesy of R. Stolzberg 1/25/
39 Courtesy of R. Stolzberg 1/25/
40 Refinery chemistry: Reforming gives lots more gasoline oc "catalysts" Crude oil Lots of gasoline 1/25/
41 1/25/2011 (from North Pole refinery) Courtesy of R. Stolzberg 41
42 Courtesy of R. Stolzberg 1/25/
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