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1.Discuss the relative acidity of alpha protons of carbonyl compounds and why the acidity of alpha protons is crucial in a Michael addition

As part of answer:

Consider the position of α hydrogens with respect to the carbonyl group.

To better understand why the α hydrogen can be removed by weak bases, consider the molecular orbitals involved and explain the role of orbitals – look at position of sigma bonds and p orbital of carbonyl

2.Illustrate the role of enolates as nucleophiles and their attack on the beta carbon of the unsaturated carbonyl compound followed by protonation of the enolate.

3.Compare 1,2 additions to carbonyls and 1,4 addtions to alpha, beta unsaturated aldehydes/ketones

4.Why does 1.4 additionpreferentally occur in the reaction under study to form Dimedone

5. Which if the two products – the keto or enol – would be expected to be favored in the reaction under study

· compare polar, polar aprotic, and non polar solvents in terms of which is expected to be favored

· include any other factors that affect whether keto or enol is favored

6. For the reaction mechanism, can decarboxylation take place without initial hydrolysis- why or why not?

7. What other by products can be produced if water enters the reaction system (other than hydrolysis of the malonate ester as a by product)