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Organic Chemistry 353-Chapter 8

Organic Chemistry 353-Chapter 8 - WhenY=HandZ= Alkenes...

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Elimination Reactions of Alkyl Halides Alkyl halides can also undergo elimination U d t th i lk Used to synthesise alkenes When Y=H and Z=Halogen Dehydrohalogenation
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Alkenes
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Elimination Mechanisms : E2 Reaction Again kinetic studies are useful to probe mechanism Transition state must involve the alkyl halide and alkoxide
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E2 and S N 2
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The Zaitsev (Saytzeff) Rule In elimination reactions, the most stable alkene usually predominates
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E1 Reaction An E1 reaction exhibits first order kinetics: An E1 reaction exhibits first order kinetics: Mechanisms of Elimination E1 Rate=k[(CH 3 ) 3 CCI]
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E1 Reaction
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Competition with S N 1 E1 and S N 1 occur together, t butyl bromide in ethanol
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Rearrangements
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Stereochemistry of the E2 Reaction Anticoplanar TS important in cyclic systems
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The Stereochemistry of E2 Reactions Antiperiplanar arrangement is required Allows for best overlap of orbitals in the developing π bond and staggered conformation is more stable Cyclohexane molecules provide experimental evidence
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The Stereochemistry of E2 Reactions Two axial cyclohexane β Hydrogens Zaitsev’s rule is satisified Zaitsev s rule is satisified
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