1. Predict the products from the two different reactions of the starting enone with two different organometallic reagents below. Assume aqueous workup.
2. In acidic deuterated water, D3O+, hydrogens are exchanged for deuterium via the keto-enol equilibrium. Provide the fully deuterated products of the reactions below.
3a. Two carbonyl compounds each with 5 carbons will produce the aldol product below. Determine the structure of the starting materials.
3b. Deprotonation with strong base lithium diisopropylamide (LDA) at low temperatures followed by addition of 3-bromo-1-pentene yields the ketone shown on the right. Predict the starting material.
4. Develop a reasonable, arrow-pushing reaction mechanism that explains the formation of the aldol condensation product below.