Problems and exercisesEnamines, imines and hydrazones
Exercise 1
Write the products of the sequence: cyclohexanone + morpholine (TsOH, −H2O); then ethyl bromoacetate; finally H3O+.
Exercise 2
The pyrrolidine enamine of 2-methylcyclohexanone has its double bond towards C6, not towards C2. Explain why and deduce which ketone is obtained on alkylation with methyl iodide and hydrolysis.
Exercise 3
What is the advantage of a metalated imine (aza-enolate) over an enamine for alkylating a ketone with 2-bromopropane? And over the lithium enolate of the ketone?