Exam 23: Carbonyl Condensation Reactions

Exhibit 23-10 Consider the reaction below to answer the following question(s). The Stork enamine reaction is a variation on the Michael reaction which utilizes an enamine nucleophile. -Refer to Exhibit 23-10.Draw the structures of the Ketone + Amine products of this reaction.

Which of the following would be classified as a Michael donor?

Exhibit 23-2 Consider the reaction below to answer the following question(s): -Refer to Exhibit 23-2.Write the complete stepwise mechanism for the reaction above.Show all intermediate structures and all electron flow with arrows.

Exhibit 23-5 Consider the reaction below to answer the following question(s). -Refer to Exhibit 23-5.This reaction is an example of:

In the alkylation of cyclohexanone,better yields are obtained by first reacting cyclohexanone with an equivalent of lithium diisopropylamide in THF and then adding the alkyl halide,rather than mixing cyclohexanone,alkyl halide,and a catalytic amount of sodium ethoxide in ethanol.Explain this observation by pointing out what the problems with the second reaction conditions might be and how the first set of reaction conditions help alleviate the problems.

In carbonyl condensation reactions,

Show how you might use a Robinson annulation reaction to synthesize the following compound.Draw the structures of both reactants and the structure of the intermediate Michael addition product.

Draw the products of the Claisen condensation of the following substance.Atoms other than carbon and hydrogen are labeled.

For which of the following will the aldol reaction go the furthest toward completion?

Exhibit 23-5 Consider the reaction below to answer the following question(s). -Refer to Exhibit 23-5.Which carbonyl compound functions as the electrophile in this reaction?

​Draw the general mechanism of a carbonyl condensation reaction between two molecules of acetaldehyde.

The product of an aldol condensation reaction is generally favored if

Exhibit 23-7 Consider the reaction below to answer the following question(s): Acetoacetic ester can be prepared by the Claisen self-condensation reaction of ethyl acetate. -Refer to Exhibit 23-7.Write the complete stepwise mechanism for this reaction.Show all electron flow with arrows and draw all intermediate structures.

Exhibit 23-10 Consider the reaction below to answer the following question(s). The Stork enamine reaction is a variation on the Michael reaction which utilizes an enamine nucleophile. -Refer to Exhibit 23-10.Show how you might use a Stork enamine reaction to prepare the following compound.

Exhibit 23-10 Consider the reaction below to answer the following question(s). The Stork enamine reaction is a variation on the Michael reaction which utilizes an enamine nucleophile. -Refer to Exhibit 23-10.On the structures above,draw arrows indicating electron flow in each step of this reaction.

Provide the indicated starting material and intermediate in the synthetic sequence below involving a Dieckmann cyclization,followed by a Robinson annulation.

Exhibit 23-2 Consider the reaction below to answer the following question(s): -Refer to Exhibit 23-2.This reaction is an example of:

Consider the following molecular model.Atoms other than carbon and hydrogen are labeled. A synthesis is set-up based upon treatment of this compound with NaOH in ethanol.This synthesis aims to produce the following substance. What is wrong with this synthesis?

Which of the following when reacted with butanal would be the most likely to produce a single aldol product?

H₃O⁺ i. SOCl₂,CHCl₃