CHEM 212 Lecture 9

CHEM 212 Lecture 9 - 9/28/2009 ORGANIC CHEMISTRY 212...

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9/28/2009 1 ORGANIC CHEMISTRY 212 Youla S. TSANTRIZOS Office: Chemistry Department Email: youla.tsantrizos@mcgill.ca Lecture 9 : September 29 th , 2009 ORGANIC CHEMISTRY 212 Chapter 6: Substitution / Elimination reactions - S N 2 / S N 1 Substitution Reactions - alkyl halides - alcohols
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9/28/2009 2 Reactivity of the Leaving Group δ + δ - Reactivity of Halogen Atoms as Leaving Groups: F - <<< Cl - << Br - <<< I - The Larger Halogen Atoms form More Stable Anions and Better Leaving Groups Leaving Group Reactivity is Opposite from Basicity Inversion of Stereochemistry H 3 CH 2 C C H 3 C H Br ( S )-2-bromobutane
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9/28/2009 3 Inversion of Stereochemistry CH 2 CH 3 C CH 3 H Br Inversion of Stereochemistry HO δ δ _ δ δ _ δ δ + 3sp 2 orbitals 1 nearly empty 2p orbital δ δ +
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9/28/2009 4 Br ( R )-2-butanol Inversion of Stereochemistry Br H 3 C H 3 C H 3 C Steric Effects of the Substrate Br H 3 C H H 3 C
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9/28/2009 5 Br H 3 C H 3 C H 3 C Steric Effects of the Substrate Br H 3 C H H 3 C HO _ HO _ HO _ HO _ NO REACTION via S N 2 Mechanism Br H 3 C H 3 C H 3 C Steric Effects of the Substrate Increasing Reactivity towards S N 2 Substitution Reactions
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6 Br H 3 C H 3 C H 3 C Substitution Reactions with t -butyl bromide 3sp 2 orbitals 1 empty 2p orbital + + Br _ CH 3 CH 3 CH 3 HO HO _ Carbocation
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CHEM 212 Lecture 9 - 9/28/2009 ORGANIC CHEMISTRY 212...

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