4-AlkenesIntroHXAdditionHLSF07

4-AlkenesIntroHXAdditionHLSF07 - Conclusion_stabilize...

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Reactions of Alkenes - Many - Extremely Useful Goal : predict reactivity based on structure. Learn with: Apply to: cholesterol ethylene •C-C sigma bonds in alkanes strong (BDE = 83 kcal/mol) •C=C π -bond much weaker BDE ( π -bond only) = 146 kcal/mol (total) - 83 kcal/mol ( σ -bond)=63 kcal/mol BDE values from Reusch, Virtual Textbook, http://www.cem.msu.edu/~reusch/OrgPage/bndenrgy.htm Recall:
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I. Electrophilic Addition Reactions 1. E + = HX: HI, HBr, HCl (not HF) A. General Reaction B. Mechanism C C X H X H C C Y Q Y Q
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C. Addition to an Unsymmetrical Alkene, 2-methylpropene C C H H H 3 C H 3 C Br H H 3 C C C H H Br H H 3 C H 3 C C C H H H Br H 3 C Regioisomers Which is favored? Look at the mechanism . Br H C C H H H 3 C CH 3
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D. Carbocations - Hybridization, Geometrty and Relative Stability H 3 C C CH 3 CH 3 H C CH 3 CH 3 H C CH 3 H H C H H Empty ______ orbital
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Unformatted text preview: Conclusion: _________stabilize + charge better than _________ WHY? 1. Alkyl groups inductively donating. H 3 C C CH 3 CH 3 H C CH 3 CH 3 H C CH 3 H H C H H 2. Hyperconjugation C C H H H H H C C H H H H H H Recall: Resonance also effects carbocation stability. H 3 C C CH 3 CH 3 H C CH 3 CH 3 H C CH 3 H H C H H H H H H Carbocation Stability Product Distribution ? Hammond’s Postulate Transition State Energy Free Energy of Activation, Δ G ‡ Rate of Reaction Review - Energy Diagrams S t a n d r F e E g y , ! G Reaction Coordinate A B C A B C A B C A D A D A + D D C D C D C Reaction Coordinate...
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