Exam 11: Carbonyl Alpha-Substitution Reactions and Condensation Reactions

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.

Identify products a and b.

Give major product(s):

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.

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

Write a resonance structure for the anion below.

How would you prepare each of the following compounds using a malonic ester synthesis? Show all intermediate structures and all reagents. -Prepare:

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

The common feature of $\alpha$ -substitution and condensation reactions of carbonyl groups:

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:

Consider the reaction below to answer the following questions. -Refer to Instructions. The weakest acid in the reaction is:

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: 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:

How would you prepare each of the following compounds using a malonic ester synthesis? Show all intermediate structures and all reagents. -Prepare:

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: 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: 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: 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: