Exam 11: Carbonyl Alpha-Substitution Reactions and Condensation Reactions

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 enolate ion in the reaction is:

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

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: Chapter 11 - Carbonyl Alpha-Substitution Reactions and Condensation Reactions Key

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

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: 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:

Write a resonance structure for the anion below.

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

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. Draw the structure of the enolate ion that is generated during the course of this reaction.

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 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:

Identify products a and b.

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

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

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

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

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.