Exam 17: Carbonyl Alpha-Substitution and Condensation Reactions

Consider the structures below to answer the following question(s). -Nitroethane [CH₃CH₂NO₂, pK_a = 8.6] is a much stronger acid than ethane [CH₃CH₃, pK_a ≈ 60]. Explain.

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.

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:

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.

How would you prepare the following compound using an alkylation reaction?

Consider the reaction sequence below to answer the following question(s). -Refer to instructions. Conversion of B into C involves hydrolysis of the ester followed by decarboxylation. On the structures provided below, show the electron flow for the decarboxylation step.