Chapter 9 - Chapter 9. The Chemistry of Alkyl halides...

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Unformatted text preview: Chapter 9. The Chemistry of Alkyl halides Saturday, November 14, 2009 Nucleophilic substitution Saturday, November 14, 2009 beta-elimination reactions Saturday, November 14, 2009 Competition between nucleophilic substitution and beta-elimination reactions Saturday, November 14, 2009 equilibria in nucleophilic substitution reactions Saturday, November 14, 2009 Reaction rates Saturday, November 14, 2009 Rate law Saturday, November 14, 2009 SN2 Reactions Saturday, November 14, 2009 Comparison of the rates of SN2 reactions and bronsted acidbase reactions Saturday, November 14, 2009 Frontside attack retention Backside attack Inversion Saturday, November 14, 2009 Saturday, November 14, 2009 Saturday, November 14, 2009 Saturday, November 14, 2009 Saturday, November 14, 2009 Saturday, November 14, 2009 E2 reaction Saturday, November 14, 2009 Rate law of the E2 reaction Saturday, November 14, 2009 Concerted mechanism of the E2 reaction Saturday, November 14, 2009 Leaving group effects on the E2 Reaction Saturday, November 14, 2009 Deuterium isotope effects in the E2 Saturday, November 14, 2009 Stereochemistry of the E2 reactions Saturday, November 14, 2009 Saturday, November 14, 2009 Regioselectivity of the E2 reactions Saturday, November 14, 2009 Saturday, November 14, 2009 SN2 vs. E2 Saturday, November 14, 2009 Saturday, November 14, 2009 SN1 and E1 Reactions SN1 & E1 First-order reactions: forming carbocation intermediate Saturday, November 14, 2009 Rearrangement Saturday, November 14, 2009 SN1 Substitution/elimination of the carbocation intermediate E1 Saturday, November 14, 2009 reactivity and product distribution Saturday, November 14, 2009 Stereochemistry of SN1 reactions Saturday, November 14, 2009 alpha-elimination reactions Saturday, November 14, 2009 using carbene to synthesize cyclopropane Saturday, November 14, 2009 Key Points nucleophilic substitution; beta-elimination; competition with substitution; Equilibria in nucleophilic substitution; reaction rates: rate law, relationship of the rate constant to the standard free energy of activation; Stereochemistry and SN2 reactions (turn inside out); effects of solvents, leaving group, nucleophilicity, alkyl substitutes; E2 Reactions: concerted mechanism, regioselectivity, stereochemistry, leaving group effects, competition with SN2, deuterium isotope effects; SN1 & E1 Reactions: rate-limiting step: carbocation intermediate formation, stereochemistry of SN1, rearrangement, product distribution; Carbene and carbenoids Saturday, November 14, 2009 11/11, Wed Reading Assignment: 377 - 399 Homework: 9.1, 9.2, 9.5b,9.7,9.8,9.9,9.10,9.13,9.15,9.35,9.39,9.54 11/13, Fri Reading Assignment: 400 - 411 Homework: 11/16, Mon Reading Assignment: 412 - 429 Homework: 11/18: None 9.26,9.27,9.34,9.45,9.48,9.51, 9.25,9.28,9.29,9.46,9.52 9 . 6 , 9 . 11 , 9 . 1 2 , 9 . 1 4 , 9 . 3 8 , 9 . 1 6 , 9 . 1 8,9.23,9.24 Saturday, November 14, 2009 ...
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