Michael Addition Practice Problems

Draw the reagents required to synthesize the compound shown below.

Draw the reagents required to synthesize the compound given below.

Predict the missing products in the following sequence.

Show how the given compound can be prepared using proper Michael donor and acceptor starting materials.

Show how the given compound can be prepared using proper Michael donor and acceptor starting materials.

Show how the given compound can be prepared using proper Michael donor and acceptor starting materials.

The reaction of lawsone and 4-chloro-2-aminophenol produces the red product shown below. Propose a mechanism for the reaction.

The following reaction occurs in acidic conditions, but a mechanism can be proposed for when it occurs in basic conditions.

Is the proposed mechanism for the basic condition shown below possible? (Note: The most acidic proton is shown.)

What products would you expect to obtain from the following reaction?

Give the main product of the reaction shown below.

Propose a method using acetoacetic ester synthesis to produce 1-cyclopentylhexane-1,5-dione.

Draw the reaction sequences that show how the following transformation happens without drawing the full mechanism.

Show the plausible reaction sequences that would show how the following transformation happened without drawing the full mechanism.

We have examined many reversible condensations in organic chemistry. The prefix retro-, derived from the Latin word meaning "backward," is frequently applied to reverse reactions. For the following reaction:

Draw the mechanism.

Draw the product of the following reaction and the final product after hydrolysis.

pyrrolidine of enamine of cyclohexanone + propyl vinyl ketone

Propose the plausible synthesis for the given transformations through the synthesis of enamine with piperidine as the secondary amine.

(i) cyclohexanone → 2-propylcyclohexan-1-one

(ii) hexan-3-one → 3-methyl-1-phenylheptan-4-one

Propose a plausible synthesis for the following compound using suitable Michael donors and acceptors.

Draw a plausible synthesis for the following compound using suitable Michael donors and acceptors.

A Michael acceptor undergoes conjugate addition, making it carcinogenic. Glutathione counteracts this by reacting with the carcinogen as shown below. Draw the expected inactivated carcinogen that forms between the carcinogen and glutathione. Represent the rest of glutathione as R.

Suggest a plausible synthesis of the following compound using a suitable Michael donor and Michael acceptor.

The following molecule can be synthesized through the Michael addition, forming a new carbon-to-carbon bond from β and γ carbons relative to the carbonyl on the left. Show the alternative way to synthesize the target molecule when the bond is formed when the β and γ carbons is relative to the right carbonyl.