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Chapter 7: Alkenes and Alkynes I

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1 Chapter 7: Alkenes and Alkynes I
CH 7-1 Introduction Structure of alkenes & alkynes Nomenclature Relative stabilities of alkenes Synthesis of alkenes via E1/E2 eliminations: E2 with small or bulky base Stereochemistry in E2 eliminations Cycloalkene eliminations Acid catalyzed alcohol dehydration Rearrangements in SN1/E1 reactions Alkene Hydrogenation (stereospecific syn addition of H2) Terminal alkynes as nucleophiles

2 Structure of Alkenes •“Un-saturated hydrocarbons” – contain C=C which is the key to understanding alkene chemical reactivity, HD = 2 • sp2 hybridization; trigonal planar; sigma and pi bonds •Each sp2 carbon has 3 sigma bonds & 1 pi bond. No C=C bond rotation due to the pi bond. s cis-2-butene p-orbitals “overlap” • Alkenes have Constitutional and Geometric isomers (cis-trans). How many isomers exist for the formula: C4H8

3 Structure of Alkynes •“Un-saturated hydrocarbons” – contain C-C triple bond. • Linear geometry; sp hybridization; sigma and pi bonds • Alkynes have Constitutional isomers (no geometric). How many isomers exist for the formula: C4H6 (Hint: nine isomers: 3 alkyne, 2 alkene, 4 ring)


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