Chapter06 - Alkene - Hydrocarbon With CarbonCarbon Double...

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1 6. Alkenes: Structure and Reactivity Based on McMurry’s Organic Chemistry , 6 th edition 2 Alkene - Hydrocarbon With Carbon- Carbon Double Bond ± Also called an olefin but alkene is better ± Includes many naturally occurring materials ± Flavors, fragrances, vitamins ± Important industrial products ± These are feedstocks for industrial processes 3 6.2 Degree of Unsaturation ± Relates molecular formula to possible structures ± Degree of unsaturation: number of multiple bonds or rings ± Formula for saturated a acyclic compound is C n H 2n+2 ± Each ring or multiple bond replaces 2 H's 4 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 H 3 C C C C C CH 3 H H H H H H H H
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2 5 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 ± Oxygen atoms - if connected by single bonds ± These don't affect the total count of H's C C C H H H H C H H H H C C C H H H H C H F F H C C C H H H H C H OH OH HO C 4 H 8 C 4 H 6 F 2 C 4 H 8 O 3 6 ± Compounds with the same degree of unsaturation can have many things in common and still be very different Degree of Unsaturation and Variation 7 If C-N Bonds Are Present ± 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 8 ± Count pairs of H's below CnH2n+2 ± Add number of halogens to number of H's (X equivalent to H) ± Don't count oxygens (oxygen links H) ± Subtract N's - they have two connections Summary - Degree of Unsaturation
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3 9 6.3 Naming of Alkenes ± Find longest continuous carbon chain for root ± Number carbons in chain so that double bond carbons have lowest possible numbers ± Rings have “cyclo” prefix CH 3 H 3 C H 3 C C C C CH 2 CH 3 1 2 5 H H H H 1,5-dimethylcyclohex-1-ene 3-methylpent-1-ene 1,5-dimethylcyclohexene or 3-methylpentene or 10 Many Alkenes Are Known by Common Names ± Ethylene = ethene ± Propylene = propene ± Isobutylene = 2- methylpropene ± Isoprene = 2-methyl-1,3- butadiene 11 6.4 Electronic Structure of Alkenes ± Carbon atoms in a double bond are sp 2 -hybridized ± Three equivalent orbitals at 120º separation in plane ± Fourth orbital is atomic p orbital ± Combination of electrons in two sp 2 orbitals of two atoms forms σ bond between them ± Additive interaction of
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Chapter06 - Alkene - Hydrocarbon With CarbonCarbon Double...

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