Exam 17: Carbonyl Alpha-Substitution and Condensation Reactions

Instructions: Consider the structures below to answer the following question(s). Refer to instructions.Rank the molecules above in order of increasing acidity (least acidic to most acidic).

Identify products a and b.

Instructions: Consider the reaction sequence below to answer the following question(s). Refer to instructions.The starting material A in this reaction sequence is called a(n)_____.

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: 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):

Instructions: Consider the structures below to answer the following question(s). -Refer to instructions.Underline the acidic hydrogen atoms in each of the molecules.

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.

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:

Instructions: Consider the reaction below to answer the following question(s). -Refer to instructions.Which carbonyl compound functions as the electrophile in this reaction?

An enolate ion

Instructions: Draw the structure of the product you would expect to obtain by Claisen condensation of the esters shown in the question(s)below.If an ester does not undergo Claisen condensation,explain why it does not. -Draw and explain:

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:

Instructions: Refer to the compounds below to answer the following question(s). - Refer to instructions.Underline all the acidic hydrogen atoms in Compounds I through IV.

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

How would you prepare 5-methyl-2-hexanone using an acetoacetic ester synthesis?

Instructions: Consider the structures below to answer the following question(s). -Refer to instructions.Rank the molecules above in order of increasing acidity (least acidic to most acidic).

Which of the following would form an enolate ion on treatment with a base?

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:

Predict the major aldol product of the following reaction.

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):