7Alkene Structure and Reactivity

7Alkene Structure and Reactivity - Based on McMurrys...

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Based on McMurry’s Organic Chemistry , 7 th edition
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Alkene - Hydrocarbon With Carbon- Carbon Double Bond Also called an olefin but alkene is better Includes many naturally occurring materials Flavors, fragrances, vitamins 2
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Why this Chapter? C-C double bonds are present in most organic and biological molecules To examine consequences of alkene stereoisomerism To focus on general alkene reaction: electrophilic addition 3
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6.1 Industrial Preparation and Use of Alkenes Ethylene and propylene are the most important organic chemicals produced (174 MMtone) 4
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Cracking by Industrial Method 5
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6.2 Calculating Degree of Unsaturation Relates molecular formula to possible structures Degree of unsaturation : number of multiple bonds or rings Formula for a saturated acyclic compound is C n H 2n+2 Each ring or multiple bond replaces 2 H's 6
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Example: C 6 H 10 Saturated is C 6 H 14 Therefore 4 H's are not present This has two degrees of unsaturation Two double bonds? or triple bond? or two rings or ring and double bond 7
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Degree of Unsaturation With Other Elements Organohalogens (X: F, Cl, Br, I) Halogen replaces hydrogen C 4 H 6 Br 2 and C 4 H 8 have one degree of unsaturation Organoxygen compounds (C,H,O) - if connected by single bonds These don't affect the total count of H's 8
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Organonitrogen compounds Nitrogen has three bonds So if it connects where H was, it adds a connection point Subtract one H for equivalent degree of unsaturation in hydrocarbon 9
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Summary - Degree of Unsaturation Count pairs of H's below C n H 2n+2 Add number of halogens to number of H's (X equivalent to H) Ignore oxygens (oxygen links H) Subtract N's - they have two connections 11
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6.3 Naming of Alkenes Name the parent hydrocarbon Number carbons in chain so that double bond carbons have lowest possible numbers Rings have “ cyclo ” prefix 12
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Many Alkenes Are Known by Common Names 13
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3 15
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Cis-Trans Isomerism in Alkenes Carbon atoms in a double bond are sp 2 -hybridized
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7Alkene Structure and Reactivity - Based on McMurrys...

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