Selectivity and Reactivity in Enolate Reactions Challenge

Question_1
Give the product of each of the following reactions:

1. KOH
2.

3. H3O+

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Selectivity and Reactivity in Enolate Reactions Challenge
Question_2

Show how you would make the following transformation and write the step-by-step mechanism.

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Selectivity and Reactivity in Enolate Reactions Challenge
Question_3

Write the step-by-step mechanism for the following reaction

The answer is the same as in Q2, except that here, OH- is the base. Form the
stabilized enolate from the 1,3-dicarbonyl, then make it do a 1,4-addition to the
α,β-unsaturated carbonyl. It is a Robinson Annulation again.

As general reminder when it comes to α,β-

unsaturated carbonyls, familiarize yourself with
reagents (Nucleophiles) that do the 1,2 (direct
addition) and those that do the 1,4 (conjugate)
addition

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