Write equations showing the expected products of the following enamine alkylation and acylation reactions. Then give the final products expected after hydrolysis of the iminium salts.

(d) piperidine enamine of cyclopentanone + methyl vinyl ketone

Show how you would accomplish each conversion using an enamine synthesis with pyrrolidine as the secondary amine.

(a) cyclopentanone → 2-allylcyclopentanone

(b) pentan-3-one → 2-methyl-1-phenylpentan-3-one

The following covalent inhibitor blocks function in a protease found in the porcine epidemic diarrhea virus by reacting with a cysteine amino acid residue (shown below) in the active site. Draw the expected complex that forms between the inhibitor and the enzyme active site (J. Med. Chem. 2017, 60, 3212–3216.) [Assume the presence of active site bases if you need them.]

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Show how the following products might be synthesized from suitable Michael donors and acceptors.

(e)

Show how cyclohexanone might be converted to the following δ-diketone (Hint: Stork).

Which of the following pairs of starting materials can be used to synthesize ${\mathrm{CH}}_3\mathrm{COCH}{2}_2\mathrm{CH}{2}_1\mathrm{COOEt}$ via a Michael addition reaction?

Determine the product in the following conjugated addition reaction.

Determine the product in the following conjugated addition reaction.