(a)
Interpretation:
To predict the product of acid-catalyzed hydrolysis of given esters.
Concept introduction:
An acid-catalyzed hydrolysis of the ester is a much faster reaction as compared to uncatalyzed hydrolysis of the ester. The addition of acid protonation of the oxygen atom of the carbonyl group and as it is a fact that an oxygen atom with positive charge has more electron withdrawing tendency than neutral atom. The more withdrawal of electron density decreases the electron density from the carbonyl carbon and make it more susceptible for the attack of the nucleophile. The acid catalyzed reaction mechanism is written as,
Therefore, products obtained by the acid catalyzed ester hydrolysis are the
(b)
Interpretation:
To predict the product of acid-catalyzed hydrolysis of given esters.
Concept introduction: An acid-catalyzed hydrolysis of the ester is a much faster reaction as compared to uncatalyzed hydrolysis of the ester. The addition of acid protonation of the oxygen atom of the carbonyl group and as it is a fact that an oxygen atom with positive charge has more electron withdrawing tendency than neutral atom. The more withdrawal of electron density decreases the electron density from the carbonyl carbon and make it more susceptible for the attack of the nucleophile. The acid catalyzed reaction mechanism is written as,
Therefore, products obtained by the acid catalyzed ester hydrolysis are the carboxylic acid and an alcohol by which ester was formed.
(c)
Interpretation:
To predict the product of acid-catalyzed hydrolysis of given esters.
Concept introduction:
An acid-catalyzed hydrolysis of the ester is a much faster reaction as compared to uncatalyzed hydrolysis of the ester. The addition of acid protonation of the oxygen atom of the carbonyl group and as it is a fact that an oxygen atom with positive charge has more electron withdrawing tendency than neutral atom. The more withdrawal of electron density decreases the electron density from the carbonyl carbon and make it more susceptible for the attack of the nucleophile. The acid catalyzed reaction mechanism is written as,
Therefore, products obtained by the acid catalyzed ester hydrolysis are the carboxylic acid and an alcohol by which ester was formed.
Want to see the full answer?
Check out a sample textbook solutionChapter 15 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
- Show the structures of the missing substance(s) in each of the following acid-base equilibria. a. CH3CH2NH2 + H2O ? + OH b. Diethylamine + H2Oarrow_forwardWhat compounds are obtained from the following hydrolysis reactions?arrow_forwardWhat products are formed from the acid-catalyzed hydrolysis of the following esters?arrow_forward
- In a base catalyzed keto-enol tautomerization of an aldehyde the first step of the mechanism is removal of the proton from the alpha carbon. removal for a proton from the carbonyl carbon. protonation of the carbonyl carbon. protonation of the carbonyl oxygen.arrow_forwardWhat is the major advantage of base-catalyzed hydrolysis of esters over acid-catalyzed hydrolysis?arrow_forwardDraw the molecules involved in the synthesis of aspirin. Is the forward reaction hydrolysis or condensation? Is the reverse reaction hydrolysis or condensation? Describe what occurs un each type of reaction with respect to acetylsalicylic acid.arrow_forward
- Carboxylic Acid Derivatives Resolve the reactions.arrow_forwardWhich of these is the most viable route for the preparation or synthesis of a carboxylic acid? O Alpha-carbon substitution of ketones O Oxidation of aldehydes O Nucleophilic acyl substitution of amides O Elimination of alcohols O Nucleophilic addition of ketonesarrow_forwardWhat hydrolysis products are formed when the following compound is treated with aqueous acid?arrow_forward
- Prepare the following substances from aldehydes or ketonesarrow_forwardWhich of the following compounds will decarboxylate when heated?arrow_forwardThe synthsis of isopentyl acetate is classified as which of the following reaction types? Acyl group substitution O Acyl group addition Acyl group oxidation Acyl group eliminationarrow_forward
- Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage LearningOrganic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,General, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage Learning
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning