3. When 2-ethylcyclohexanone is treated with LDA (in the solvent THF), followed by ethyl bromide, two different alkylated products are formed. Answer the following questions about this reaction. 1) LDA THE two products 2) CH CH Br 3. a. What is LDA and what is its purpose? 3. b. Draw mechanisms for the reactions and show how the two different products are formed. Product A Mechanism Product B Mechanism

3. c. Draw an energy diagram for the formation of both products A (Solid Line) and product B (Dashed Line). Explicitly label the reactants, products, activation energies, and the structure(s) of any intermediates. Product A —- Product B Reaction Progress 3. d. Use the reaction energy diagram to help you explain which product you predict would be formed preferentially at low temperature. 3. e. Use the reaction energy diagram to help you explain which product you predict would be formed preferentially at higher temperature.