Chapter 6, Problem 6.52P

As we have seen in this chapter, carbon-carbon double bonds are electron-rich regions that are attacked by electrophiles (e.g., HBr); they are not attacked by nucleophiles (e.g., diethylamine).

However, when the carbon-carbon double bond has a carbonyl group adjacent to it, the double bond reacts readily with nucleophiles by nucleophilic addition (Section 19.8).

Account for the fact that nucleophiles add to a carbon-carbon double bond adjacent to a carbonyl group and account for the regiochemistry of the reaction.