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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

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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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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