Acid-Catalyzed Ester Hydrolysis Practice Problems

True or False. The HB⁺ in the mechanism for the acid-catalyzed hydrolysis of esters is most likely to be H₃O⁺.

Draw a mechanism for the acid-catalyzed reaction of propionic acid and ethanol to form ethyl propionate, including all curved arrows. As a guide, consider the mechanism for the acid-catalyzed hydrolysis of an ester, where HB⁺ and :B represent the species that donate and remove protons, respectively.

Determine the acid-catalyzed hydrolysis products of the ester given below.

Consider the following derivative of the known sweetener, aspartame. 

What are the products obtained when it undergoes complete hydrolysis in a dilute solution of HCl?

Predict the product(s) for the following reaction and propose a mechanism.

Propose the reagents required for the following conversion.
butan-1-ol → 2-hydroxypentanoic acid

Consider the following compound that has been labeled with the O-18 isotope of oxygen.

Write a plausible mechanism for the hydrolysis of this compound under acidic conditions.

The general reaction below is the Reformatsky reaction wherein an organozinc reagent is used to add to the carbonyl group of an aldehyde or ketone. However, nucleophilic addition does not occur for an ester group because the organozinc is less reactive than a Grignard reagent. To prepare the organozinc reagent, an α-bromo ester is treated with zinc.

Using the Reformatsky reaction, show the following compound can be synthesized.

Provide a plausible mechanism for the acid-catalyzed hydrolysis reaction shown below.

Give a reasonable mechanism for the acid-catalyzed hydrolysis reaction illustrated below.

The acidic and basic hydrolyses of a nitrile differ slightly. In acidic hydrolysis, the cyano group's nitrogen is protonated first to increase its electrophilicity, allowing water, a weak nucleophile, to attack. Deprotonation of oxygen follows, forming an enol tautomer of an amide, which is then subjected to proton transfer (tautomerism) to produce the amide product. Draw the mechanism of the acid-catalyzed hydrolysis of cyclohexanecarbonitrile to cyclohexanecarboxamide.

Which of the two parts of the acid-catalyzed hydrolysis mechanism of an ester and an amide are similar?

Determine the product of the following reaction.

Which of the following esters is more reactive towards hydrolysis?

Which of the following compounds is more reactive toward hydrolysis?

Write the similarities between the following two mechanisms:

• acid-catalyzed hydrolysis of methyl acetate and acid-catalyzed hydrate formation from acetone.

For the following compounds, identify the products that would be obtained upon complete hydrolysis:

Show how you could accomplish the following conversion.

Show how you could accomplish the following conversion.

Determine the alkyl halides that produce the following carboxylic acids by reacting with sodium cyanide followed by heating in presence of aqueous acid.

I. valeric acid

II. 2-methylbutanoic acid

Secondary alkyl halides react with the hydroxide ion to form both alcohol and alkene. Provide a method for producing cyclopentanol from bromocyclopentane that produces little or no cyclopentene.

Identify the correct reagents that can be used to carry out the following conversions.

Show how acetophenone can be synthesized from ethyl benzene in a high yield.

Propose the synthesis of the following compound from the given starting material and any necessary reagents.

Suggest a method to synthesize the following compound using the provided starting material and any organic or inorganic reagents.

How can you synthesize the following compound using the provided starting material and any required reagents?

What reagents are required to produce the following compound using the given starting material?

Determine the major product of the reaction below.

Draw a suitable mechanism for each of the reactions given below.

Why do the nitro groups in the intermediate in the reaction below alter the relative leaving inclinations of the carboxy and 2,3-dinitrophenoxy groups?

The nitro group makes:

Draw the mechanism of the uncatalyzed hydrolysis of ethyl butyrate.

The reverse of the Fischer esterification is the acid-catalyzed hydrolysis of an ester. Suggest a mechanism for the acid-catalyzed hydrolysis of methyl propionate.

Draw the mechanism for the acid-catalyzed hydrolysis of ethyl butyrate.