Experimental procedure (for values see table on the below)

1. The ketone starting material was dissolved in 10 ml diethyl ether. This solution was then added dropwise with stirring to round bottom flask containing a cold solution of 20 ml diethyl ether and lithium diisopropylamide. This reaction was then stirred for an additional 10 minutes at room temperature.

2. The unknown electrophile was dissolved in 5 ml diethyl ether and then slowly added dropwise to the reaction. This solution was stirred for an additional 30 at room temperature, then transferred to a separatory funnel.

3. 20 ml of water was added and the funnel was shaken. After the layers separated, the organic layer was collected and the aqueous layer was discarded.

4. The organic later was evaporated to concentrate the sample prior to purification by column chromatography. UV active fractions were collected and evaporated, then weighed and analyzed by proton NMR, carbon NMR, and Br2 unsaturation tests.

Questions to be answered in presentations:

1. Draw the mechanism for the reaction and your predicted electrophile structure. Predict potential products and side products for this reaction. Think about questions such as 1) What is the limiting reagent in this reaction, and how does this affect what compounds you expect to collect after the reaction? 2) what is the purpose of adding the ketone to LDA, instead of the other way around? 3) How does the amount of conjugation in your final product affect your predicted reaction rate and side products? 4) Rank order your predicted products and side products in terms of overall polarity. How does this affect their elution time during column chromatography?

2. Compare this to your data set. Did you isolate all of the predicted products? Why or why not?

3. Does your experimental data (HNMR, CNMR, distillation data, unsaturation test data) support your predictions for this reaction? DISCUSS IN DEPTH.

Consider the reaction below:

Note that the molecular weight and formula is given for your unknown electrophile.