Exam 17: Carbonyl Alpha-Substitution and Condensation Reactions

Instructions: Consider the reaction sequence below to answer the following question(s). -Refer to instructions.Conversion of A into B is a type of reaction termed _____.

Instructions: Draw the structure of the aldol self-condensation product of each compound for the following question(s).If a compound does not undergo aldol self-condensation,explain why it does not. -Draw and explain:

Nitroethane [CH₃CH₂NO₂,pK_a = 8.6] is a much stronger acid than ethane [CH₃CH₃,pK_a » 60].Explain.

Instructions: Give the major organic product(s)of each reaction or sequences of reactions for the following question(s).Show all relevant stereochemistry. -Give major product(s):

Predict the major aldol product of the following reaction.

Instructions: Refer to the compounds below to answer the following question(s). -Refer to instructions.Draw the structure for the enol and enolate ions corresponding to Compound I.

Instructions: Refer to the compounds below to answer the following question(s). -Refer to instructions.Choose the most acidic compound from Compounds I - IV.Explain your choice.

Instructions: Each of the following compounds in the following question(s)can be prepared by a mixed aldol condensation reaction. a)Give the structures of the aldehyde and/or ketone precursors for each aldol condensation product and formulate the reaction. b)Give the structure of the intermediate aldol product. -Refer to instructions.Use the following compound:

Instructions: Consider the reaction below to answer the following question(s). -Refer to instructions.Draw the structure of the enolate ion that is generated during the course of this reaction.

Instructions: Consider the reaction below to answer the following question(s). -Refer to instructions.Draw the structure of the enolate ion that is generated during the course of this reaction.

Instructions: The Stork enamine reaction is a variation on the Michael reaction that utilizes an enamine nucleophile.Use this information to answer the following question. -Refer to instructions.Draw the structures of the ketone and amine products of this reaction.

Which of the following does not possess an enol form? Explain your choice.

How would you prepare the following compound using an alkylation reaction?

Instructions: Each of the following compounds in the following question(s)can be prepared by a mixed aldol condensation reaction. a)Give the structures of the aldehyde and/or ketone precursors for each aldol condensation product and formulate the reaction. b)Give the structure of the intermediate aldol product. -Refer to instructions.Use the following compound:

Instructions: Consider the reaction below to answer the following question(s). -Refer to instructions.The product of this reaction is:

Instructions: Consider the reaction below to answer the following question(s). Refer to instructions.This reaction is an example of:

Instructions: Each of the following compounds in the following question(s)can be prepared by a mixed aldol condensation reaction. a)Give the structures of the aldehyde and/or ketone precursors for each aldol condensation product and formulate the reaction. b)Give the structure of the intermediate aldol product. -Refer to instructions.Use the following compound:

Instructions: Refer to the compounds below to answer the following question(s). -Refer to instructions.Indicate which hydrogens in Compound II are the most acidic.Explain your answer.

When treated with base and heat,the following diketone undergoes an intramolecular aldol reaction followed by dehydration to produce cis-jasmone,a perfume component.Draw the structure of the product.

Instructions: Draw the structures of the precursors to the Michael reaction products shown in the question(s)below.Label the Michael donor and the Michael acceptor in each case and formulate the reaction. -Draw and label: