Exam 21: Carboxylic Acid Derivatives

Which of the following reactions is favorable, in the direction indicated, under fairly "normal" laboratory conditions?

Provide a detailed, stepwise mechanism for the base-mediated transesterification of methyl benzoate with sodium ethoxide.

Propose a synthesis of 2-phenylethylamine from toluene and any other necessary reagents.

Provide a detailed, stepwise mechanism for the acid-catalyzed transesterification of ethyl acetate with n-propanol.

Assuming equal molecular weights, mark all of the following compounds, indicated by their functional group, that would have a higher boiling point than an alcohol. (More than one answer is possible.)

What reagents are needed to complete the following reaction?

Provide the IUPAC name of the following compound.

What type of compound results from the reaction of an acid chloride and a 2° amine?

Name the compound which results when propyl benzoate is heated in a large excess of ethanol in the presence of catalytic acid.

Which sequence ranks the following carboxylic acid derivatives in order of increasing rate of hydrolysis?

Provide the major organic product in the reaction of 3-methylpentanoic acid with CH₂N₂.

Provide the major organic product in the reaction of cyclopentanecarbonyl chloride with sodium formate.

Provide the name of the compound shown below.

What are the products from the reaction of excess methyl magnesium bromide with ethyl acetate followed by H₃O⁺?

Provide the structure of cyclohexyl formate.

Provide the structure of (R)-4-ethoxypentanenitrile.

List the following four carboxylic acid derivatives, ester, anhydride, amide, and acid halide, in order of increasing reactivity in nucleophilic acyl substitution reactions. Start with the least reactive derivative.

Predict the major product of the following reaction.

Carbonated beverages typically have pHs below 7.0. What acid is present which lowers the pH? Show the reaction by which it is formed.

The following compound is a tumor growth inhibitor (J. Med. Chem. 2011, 1789). Circle all carbon centers that are at the same oxidation state as a carboxylic acid.