Exam 11: Carbonyl Alpha-Substitution Reactions and Condensation Reactions

Predict the major aldol product of the following reaction.

An enolate ion

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.

Write a resonance structure for the anion below.

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?

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

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 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).

Consider the reaction below to answer the following questions. Refer to Instructions. On the structures provided above, draw arrows indicating elctron flow in the generation of the intermediate C.

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):

How would you prepare 3-phenylpropanoic acid using a malonic ester synthesis?

Consider the reaction below to answer the following questions. Refer to Instructions. The strongest base in the reaction is:

Which of the following is common to both tautomers and resonance forms of a compound?

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. Choose the most acidic compound from Compounds I - IV. Explain your choice.