(a)
Interpretation:
The complete, detailed mechanism and the overall product for the given reaction is to be drawn.
Concept introduction:
The ester is hydrolyzed to the carboxylic acid under acidic conditions, so no strong base should appear in the mechanism. Water is the nucleophile, and the leaving group is a molecule of ethanol. Proton transfer steps are incorporated to avoid the appearance of strong bases.
Answer to Problem 21.14P
The mechanism and product for the given reaction is:
Explanation of Solution
In Step 1 of the mechanism, the acid protonates the ester’s carbonyl group, and in Step 2, water attacks the carbonyl
The complete, detailed mechanism and the overall product for the given reaction is drawn by acid-catalyzed ester hydrolysis.
(b)
Interpretation:
The complete, detailed mechanism and the overall product for the given reaction is to be drawn.
Concept introduction:
This is an acid-catalyzed transesterification, and a new ester is formed.
Answer to Problem 21.14P
The mechanism and product for the given reaction is:
Explanation of Solution
In Step 1 of the mechanism, the acid protonates the ester’s carbonyl group, and in Step 2,
The complete, detailed mechanism and the overall product for the given reaction is drawn by acid-catalyzed transesterification.
(c)
Interpretation:
The complete, detailed mechanism and the overall product for the given reaction is to be drawn.
Concept introduction:
This is an acid catalyzed amide hydrolysis which produces a carboxylic acid. Water acts as the nucleophile in this acid-catalyzed nucleophilic addition–elimination mechanism, and the leaving group is a molecule of
Answer to Problem 21.14P
The mechanism and product for the given reaction is:
Explanation of Solution
In Step 1 of the mechanism, the acid protonates the ester’s carbonyl group, and in Step 2, water attacks the carbonyl
The complete, detailed mechanism and the overall product for the given reaction is drawn by acid-catalyzed amide hydrolysis.
(d)
Interpretation:
The complete, detailed mechanism and the overall product for the given reaction is to be drawn.
Concept introduction:
This is an acid catalyzed ester hydrolysis which produces a carboxylic acid. Water acts as the nucleophile in this acid-catalyzed nucleophilic addition–elimination mechanism, and the leaving group is a molecule of alcohol. Proton transfer steps are incorporated to avoid the appearance of strong bases.
Answer to Problem 21.14P
The mechanism and product for the given reaction is:
Explanation of Solution
In Step 1 of the mechanism, the acid protonates the ester’s carbonyl group, and in Step 2, water attacks the carbonyl
The complete, detailed mechanism and the overall product for the given reaction is drawn by acid-catalyzed ester hydrolysis.
(e)
Interpretation:
The complete, detailed mechanism and the overall product for the given reaction is to be drawn.
Concept introduction:
This is Fischer esterification reaction.
Answer to Problem 21.14P
The mechanism and product for the given reaction is:
Explanation of Solution
In Step 1 of the mechanism, the acid protonates the acid’s carbonyl group, and in Step 2,
The complete, detailed mechanism and the overall product for the given reaction is drawn by Fischer esterification reaction.
(f)
Interpretation:
The complete, detailed mechanism and the overall product for the given reaction is to be drawn.
Concept introduction:
This is an acid catalyzed amide hydrolysis which produces a carboxylic acid. Water acts as the nucleophile in this acid-catalyzed nucleophilic addition–elimination mechanism, and the leaving group is a molecule of amine. Proton transfer steps are incorporated to avoid the appearance of strong bases.
Answer to Problem 21.14P
The mechanism and product for the given reaction is:
Explanation of Solution
In Step 1 of the mechanism, the acid protonates the ester’s carbonyl group, and in Step 2, water attacks the carbonyl
The complete, detailed mechanism and the overall product for the given reaction is drawn by acid-catalyzed amide hydrolysis.
Want to see more full solutions like this?
Chapter 21 Solutions
ORGANIC CHEM BUNDLE
- Draw the complete, detailed mechanism for the reaction shown here. Will the product be optically active? Explain.arrow_forwardPredict the major products of the following reactions. Draw the complete, detailed mechanism that leads to the formation of each of those products.arrow_forwardDraw the complete, detailed mechanism for the following reaction.arrow_forward
- Draw a complete, detailed mechanism for the reaction shown here.arrow_forwardPredict the major product of each of the following reactions and provide the complete, detailed mechanismarrow_forwardDraw the complete mechanism and the major organic product for each of the following reactions.arrow_forward
- Determine the major product of each reaction in Problem and draw the complete, detailed mechanism. Pay attention to stereochemistry where appropriate.arrow_forward(SYN) Show how to synthesize the following molecule from any compounds containing two carbons. Draw the complete, detailed mechanism for the reaction.arrow_forwardHelp, explain in detail please. Thank you! Did the overal reaction shown here occur by and SN2, Sn1, E2, or E1 mechanism? How do you know? Draw the complete, detailed mechanism to account for the formation of both products.arrow_forward
- Draw a complete, detailed mechanism for the following reaction. A key intermediate is provided.arrow_forwardHalogenation using the mixed halogen ICl can feasibly lead to two different products, as shown here. Draw the complete, detailed mechanism for the formation of each product. Which do you think is the major product? Why?arrow_forwardPlease draw the complete, detailed mechanism of the reaction step by step.arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY