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`OR OR Benzoate esters can undergo either acid- or base-catalyzed hydrolysis as shown below. HOR + HOR (base-catalyzed) (acid-catalyzed) The base-catalyzed hydrolysis of a series of p-substituted ethyl benzoates showed a linear Hammett plot (p = +2.19). OEt, H20 HO. ELOH Op +0.78 +0.63 +0.23 -0.17 -0.36 -0.66 NO2 Br CH3 OH NH2 The reaction mechanism can be described by the general scheme shown below. slow reactants intermediate products a. Which substituents exert the most stability on the system? Explain your answer. b. Plot the reaction profile (potential energy diagram) to show the reaction pathway. Assume a negative AH°. Be sure to label all parts of the diagram. c. Propose a structure for TS1. Is this early or late? Explain. d. When the same reaction is performed under acid-catalyzed conditions, the Hammett plot changes directions (p = -3.25 to p = +2.00). Propose a mechanism to account for this observation, (Hint: consider what the o value tells you about the TS.) కీర్ జిలేర్కే

`OR OR Benzoate esters can undergo either acid- or base-catalyzed hydrolysis as shown below. HOR + HOR (base-catalyzed) (acid-catalyzed) The base-catalyzed hydrolysis of a series of p-substituted ethyl benzoates showed a linear Hammett plot (p = +2.19). OEt, H20 HO. ELOH Op +0.78 +0.63 +0.23 -0.17 -0.36 -0.66 NO2 Br CH3 OH NH2 The reaction mechanism can be described by the general scheme shown below. slow reactants intermediate products a. Which substituents exert the most stability on the system? Explain your answer. b. Plot the reaction profile (potential energy diagram) to show the reaction pathway. Assume a negative AH°. Be sure to label all parts of the diagram. c. Propose a structure for TS1. Is this early or late? Explain. d. When the same reaction is performed under acid-catalyzed conditions, the Hammett plot changes directions (p = -3.25 to p = +2.00). Propose a mechanism to account for this observation, (Hint: consider what the o value tells you about the TS.) కీర్ జిలేర్కే

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter18: Functional Derivatives Of Carboxylic Acids
Section: Chapter Questions
Problem 18.59P
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`OR POR H* Benzoate esters can undergo either acid- or base-catalyzed hydrolysis as shown below. + HOR ОН + HOR (base-catalyzed) (acid-catalyzed) The base-catalyzed hydrolysis of a series of p-substituted ethyl benzoates showed a linear Hammett plot (p = +2.19). OEt, H20 ELOH NO2 CN Br CH3 OH +0.78 +0.63 +0.23 -0.17 -0.36 NH2 -0.66 The reaction mechanism can be described by the general scheme shown below. slow reactants intermediate products a. Which substituents exert the most stability on the system? Explain your answer. b. Plot the reaction profile (potential energy diagram) to show the reaction pathway. Assume a negative AH°. Be sure to label all parts of the diagram. c. Propose a structure for TS1. Is this early or late? Explain. d. When the same reaction is performed under acid-catalyzed conditions, the Hammett plot changes directions (p = -3.25 to p = +2.00). Propose a mechanism to account for this observation. (Hint: consider what the p value tells you about the TS.)
Transcribed Image Text:`OR POR H* Benzoate esters can undergo either acid- or base-catalyzed hydrolysis as shown below. + HOR ОН + HOR (base-catalyzed) (acid-catalyzed) The base-catalyzed hydrolysis of a series of p-substituted ethyl benzoates showed a linear Hammett plot (p = +2.19). OEt, H20 ELOH NO2 CN Br CH3 OH +0.78 +0.63 +0.23 -0.17 -0.36 NH2 -0.66 The reaction mechanism can be described by the general scheme shown below. slow reactants intermediate products a. Which substituents exert the most stability on the system? Explain your answer. b. Plot the reaction profile (potential energy diagram) to show the reaction pathway. Assume a negative AH°. Be sure to label all parts of the diagram. c. Propose a structure for TS1. Is this early or late? Explain. d. When the same reaction is performed under acid-catalyzed conditions, the Hammett plot changes directions (p = -3.25 to p = +2.00). Propose a mechanism to account for this observation. (Hint: consider what the p value tells you about the TS.)
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