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Exam 21: Carboxylic Acid Derivatives

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Question 61

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

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Question 62

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

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Question 63

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

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.)

Provide the IUPAC name of the following compound.

What reagents are needed to complete the following reaction?

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.

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

Provide the structure of cyclohexyl formate.

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

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

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

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

Provide the name of the compound shown below.

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.

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

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

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

Predict the major product of the following reaction.

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