SN1 Distillation 2011 SPRING revised 2011.03.10

SN1 Distillation 2011 SPRING revised 2011.03.10 - SN1:...

Info iconThis preview shows pages 1–5. Sign up to view the full content.

View Full Document Right Arrow Icon
Click to edit Master subtitle style 4/27/11 SN1: Unimolecular Nucleophilic Substitution Simple Distillation Laboratory 6
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
4/27/11 Nucleophilic Substitution Mechanisms: SN2 and SN1 H 3 C Br H 3 C OH H H Br OH H 3 C OH -Br H 3 C OH H 3 C Br H H 3 C CH 3 H 3 C CH 3 CH 3 CH 3 H 3 C Br -H 2 O SN2: Bimolecular, One-Step, Concerted, Transition State with Inversion SN1: 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
Background image of page 2
4/27/11 Mechanism of your reaction OH OH H O H H Cl Cl Rate determining step Fast Fast HCl
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Experimental procedure Ø Shake t -amyl alcohol with conc. HCl to effect reaction Ø Separate the layers, which layer is which? Ø Wash organic layer Ø Aq NaCl- removes bulk water from organic layer Ø Aq NaHCO3- remove residual HCl from organic layer BE CAREFUL ABOUT FOAMING! Ø
Background image of page 4
Image of page 5
This is the end of the preview. Sign up to access the rest of the document.

Page1 / 17

SN1 Distillation 2011 SPRING revised 2011.03.10 - SN1:...

This preview shows document pages 1 - 5. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online