CHEM 212 Lecture 10

CHEM 212 Lecture 10 - 9/30/2009 ORGANIC CHEMISTRY 212...

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9/30/2009 1 ORGANIC CHEMISTRY 212 Youla S. TSANTRIZOS Office: Chemistry Department Email: youla.tsantrizos@mcgill.ca Lecture 10 : October 1 st , 2009 ORGANIC CHEMISTRY 212 Chapter 6: Substitution / Elimination reactions - S N 2 / S N 1 Substitution Reactions - Carbocation Rearrangment - E1 / E2 Elimination reactions
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9/30/2009 2 Carbocation Rearrangement CH 3 CH 2 OH heat + Bromide (Br - ) is a Good leaving group! Ethanol is a weak nucleophile Carbocation Rearrangement CH 3 CH 2 OH heat + Bromide (Br - ) is a Good leaving group! Ethanol is a weak nucleophile ( S )-2-ethoxy-3-methylbutane ( R )-2-ethoxy-3-methylbutane
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9/30/2009 3 Carbocation Rearrangement CH 3 CH 2 OH heat + Bromide (Br - ) is a Good leaving group! Ethanol is a weak nucleophile Hydride Shift 3 o most stable carbocation 2-ethoxy-2-methylbutane NOT chiral CH 3 CH 2 OH Carbocation Rearrangement CH 3 CH 2 OH heat + +
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9/30/2009 4 Details of Reaction Mechanism + O C H 3 C H H H H 3 C CH 3 CH 3 H O C CH 3 H H H CH 3 CH 2 OH Details of Reaction Mechanism + CH 3 CH 2 OH H 3 C CH 3 CH 3 H O C CH 3 H H H
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9/30/2009 5 Carbocation Rearrangement CH 3 CH 2 OH heat + Carbocation Rearrangement CH 3 CH 2 OH heat + +
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CHEM 212 Lecture 10 - 9/30/2009 ORGANIC CHEMISTRY 212...

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