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SN1,SN2 Reaction

If a positive result does not occur in 1 min, continue timing but start a test on a new compound (i. e. do experiments in parallel).

PART A:  REACTIVITY OF BROMIDES TOWARD SODIUM IODIDE.

Sodium Iodide in acetone. In this part of the experiment you will test the reactivity of several alkyl halides under S_N2 conditions.  In acetone solution, other alkyl halides can be converted to alkyl iodides.  Although we might expect such a reaction to be reversible, it can be driven forward by using anhydrous acetone as the solvent.  Sodium iodide is soluble in this solvent, whereas sodium chloride and sodium bromide are not.  If a reaction occurs, a precipitate of sodium bromide or sodium chloride will form.

Directions: Use scrupulously dry test tubes for this experiment.  Add 2 drops of the liquid to be tested to about 2 mL of a 15% solution of sodium iodide in anhydrous acetone.  Mix the contents and note the time required for a precipitate to form up to 15 minutes.  Test each of the following organic bromides:  1-bromobutane, 2-bromobutane, t-butyl bromide, benzyl bromide, and bromobenzene.  Report your results in tabular form.