CHEM 350 -  Principles of Organic Chemistry I
Prof. T Nalli, Fall 2006, Winona State University

Expt 5. Mechanistic study of an S_N reaction. Competitive nucleophiles. Gas chromatography, refractive index, and proton NMR.

References. Pavia Expt 21 and Techniques 22, 24 and 26. Smith Chapter 7. 

You will carry out experiment 21 (all three parts) in the Pavia text. For part A you will join together with another team in a "supergroup" of 6 (same supergroups as in Expt 2 please). One team in your supergroup should carry out the experiment using 1-butanol as the reactant and the other team using 2-butanol.

Gas chromatography and ¹H NMR will be used for the analysis of the part A reactions. Refractive index and ¹H NMR will be used for part B.

Procedure modifications: The reflux apparatus diagramed on page 184 is close to that which you will be using. However, no drying tube with wet glass wool is necessary at the top since we will be carrying out the reaction in a fume hood. (The top of the reflux condenser is merely left open to the air.) Also, you will use a sand bath (not an aluminum block) as the heat source. The sand bath consists of a thermowell filled with sand and plugged into the variable voltage outlet under each fume hood. Also, I strongly recommend clamping the neck of the flask to the ring stand (rather than clamping the condenser) as that makes securing the flask and condenser together (we do not have the screw joint attachments diagramed) unnecessary because gravity will do the job.