Exam 22: Condensations and Alpha Substitutions of Carboxyl Compounds

The following structure was used in the synthesis of a complex natural product shown to have cytotoxic activity (Org. Lett. 2006, 5585). Show how this structure may be constructed by a Robinson annulation by indicating the necessary starting materials.

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

Provide the sequence of reagents needed to convert (CH₃CH₂O₂C)₂CH₂ to 2,5-dimethylhexanoic acid.

Predict the structure of the expected product of the following reaction.

What two starting materials yield OHCCH₂CO₂CH₂CH₃ as the crossed Claisen condensation product?

Complete the following reaction by filling in the necessary reagents.

Predict the starting materials necessary for the following Robinson annulation.

Provide the major organic product of the following reaction.

The relationship between ketones and their corresponding enols is one of ________.

What crossed-aldol product results when propanal is heated in the presence of excess 2,2-dimethylpropanal and sodium hydroxide?

How could you make cyclohexanecarboxylic acid from 5-bromopent-1-ene?

Predict the outcome of the following reaction.

What reagents are needed to complete the following synthesis?

Provide the major organic product of the reaction shown below.

Provide the structure of the more stable enol tautomer of 1-phenyl-2-octanone.

What product results when an aldol is dehydrated?

Provide the structure of the ester that would undergo self-condensation to yield the shown below.

Provide the structure of the product which results from the base-catalyzed condensation followed by dehydration between benzophenone and propanal.

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

What is the carbon nucleophile which attacks molecular bromine in the acid-catalyzed α-bromination of a ketone?