Fischer Esterification Practice Problems

Write the synthesis of ethyl propionate starting with a carboxylic acid as one of the reagents.

Identify the product of the following reaction. Hint: Draw the mechanism to identify the product.

In a laboratory, a researcher added dicyclohexylacetic acid to an acidic solution of cyclohexanol but failed to acquire an ester. Identify the reason that prevented esterification of dicylohexylacetic acid.

Acetic acid is reacted with ethanol-¹⁸O in acidic conditions. Identify the labeled product(s) formed.

Show how Fischer esterification might be used to form isopropyl propionate.

Suggest a suitable synthetic approach to carry out the following reactions with good yields.

Draw the structures of the major products expected from the following acid-catalyzed esterification reactions.

a. (CH₃)₂CHCH₂COOH + CH₃CH₂OH ⇌

b. CH₃CH₂OH + HNO₃ →

c. 2 (CH₃)₂CHCH₂OH + H₃PO₄ ⇌

Draw a suitable mechanism for the esterification of 3-methylbutanoic acid with methanol.

Draw the expected products of the esterification of the pairs below.

Draw the reactants needed to produce ethyl benzoate using Fischer esterification. Suggest a method for the reaction to be driven to completion.

Propose the best reagents for the synthesis shown below.

Write the product formed in the reaction given below

Show how to synthesize each of the compounds shown below using alanine as your starting material. Give the structure of each product in your answer.
(i) alanine ethyl ester
(ii) (cyclohexanecarbonyl) alanine

Propose a synthesis for the following compound with acetaldehyde as a starting material.

Show how the following synthesis can be carried out:

Use any necessary reagents and solvents.

Determine the structures of the alcohol and acid chloride required to form the esters shown below.

People had different ideas about the mechanism of Fischer esterification, and it wasn't until 1938 that Irving Roberts and Harold Urey of Columbia University used isotopic labeling to track how the oxygen in the alcohol moved through the reaction. Using the same method, propose a mechanism for the reaction of propanoic acid and methanol that has the isotope ¹⁸O in it with acid as a catalyst.