SN1 Distillation 2011 SPRING revised 2011.03.10

SN1 Distillation 2011 SPRING revised 2011.03.10 - SN1...

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4/27/11 1 S N 1: Unimolecular Nucleophilic Substitution Simple Distillation Laboratory 6 Nucleophilic Substitution Mechanisms: S N 2 and S N 1 S N 2: Bimolecular, One-Step, Concerted, Transition State with Inversion S N 1: Unimolecular, Two Steps, Carbocation Intermediate Transition State Trigonal Bipyramidal 180°Backside Attack By Nucleophile Carbocation Planar Ionization Slow Step Rate Limiting Nucleophile Attack Fast Step On Both Faces 1° > 2°> 3° Good Nucleophile 3°> 2°> 1° Stable Carbocation Polar, Protic Solvents Inverted Stereochemistry
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4/27/11 2 Mechanism of your reaction Experimental procedure Shake t -amyl alcohol with conc. HCl to effect reaction Separate the layers, which layer is which? Wash organic layer Aq NaCl - removes bulk water from organic layer Aq NaHCO 3 - remove residual HCl from organic layer BE CAREFUL ABOUT FOAMING! Dry organic layer Purify by distillation
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4/27/11 3 Notes: Carbonate Foaming Sodium bicarbonate plus HCl makes CO 2
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