Exam 17: Carbonyl Alpha-Substitution and Condensation Reactions

Draw the structure of the diastereomer that is formed preferentially in the following reaction:

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.

Give the major organic product(s) of each reaction or sequences of reactions for the following question(s). Show all relevant stereochemistry. -How would you prepare 3-phenylpropanoic acid using a malonic ester synthesis?

The common feature of α-substitution and condensation reactions of carbonyl groups:

Rank the following hydrogens in terms of decreasing acidity (most acidic > least acidic):

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:

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.

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):

Give the major organic product(s) of each reaction or sequences of reactions for the following question(s). Show all relevant stereochemistry. -How would you prepare 5-methyl-2-hexanone using an acetoacetic ester synthesis?

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

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:

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:

Which of the following would form an enol on treatment with an acid?

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) _____.

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.

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:

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

Identify products a and b.

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:

An enolate ion