Exam 22: Condensations and Alpha Substitutions of Carboxyl Compounds

Provide the structure of the major organic product which results when PhCH₂CHO is treated with NaOH.

What are the two key resonance structures for an enamine? Label the major and minor contributors.

The following compound isolated from a marine sponge has been found to have anti-tubercular activity (Tet. Lett. 2007, 8851). Show how it may be constructed by an aldol reaction by drawing a structure of the starting material.

Provide a detailed, stepwise mechanism for the acid-catalyzed enolization of acetaldehyde.

The following compound was found to inhibit HIV-1 (J. Med. Chem. 2011, 1812). Predict the structure of the hydrolysis product.

Provide the major organic product of the following reaction.

Which of the following will react most slowly with an enamine?

The α-halogenation of cyclohexanone:

Provide the major organic product of the reaction shown below.

Predict the starting materials necessary for the following Robinson annulation.

Show how an enolate can add to a carbonyl.

Name the product which results when ethyl butanoate is treated with sodium ethoxide followed by neutralization.

Which set of reagents would best accomplish the following transformation?

Predict the outcome of the following reaction.

What product results when pentanal is heated with sodium hydroxide?

Provide the major organic product of the following reaction sequence.

(S)-2-Methylbutanal ________ upon sitting in an acidic or a basic aqueous solution.

Provide the structure of the intramolecular aldol condensation/dehydration product that results when 2,6-heptanedione is heated in base.

Provide the major organic product of the following reaction.

Which of the following is the best Michael acceptor?