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c. A landmark study into the mechanism of acetal chemistry started with radiolabeled benzaldehyde, wherein the oxygen of the aldehyde was replaced with its heavier isotope oxygen-18 (1®O). The radiolabeled aldehyde was treated with non-radiolabeled n-butyl alcohol in the presence of strong acid catalyst as shown in the complete reaction equation shown below, without radiolabeling in the products. Based on your knowledge of the reaction mechanism, circle any oxygen atom(s) in the products shown that should be radiolabeled, and explain your logic in one sentence. Но. `H + H20 H* cat.

c. A landmark study into the mechanism of acetal chemistry started with radiolabeled benzaldehyde, wherein the oxygen of the aldehyde was replaced with its heavier isotope oxygen-18 (1®O). The radiolabeled aldehyde was treated with non-radiolabeled n-butyl alcohol in the presence of strong acid catalyst as shown in the complete reaction equation shown below, without radiolabeling in the products. Based on your knowledge of the reaction mechanism, circle any oxygen atom(s) in the products shown that should be radiolabeled, and explain your logic in one sentence. Но. `H + H20 H* cat.

Chemistry
Chemistry
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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
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please answer part c 

6. Though we take it for granted nowadays, the mechanism of acetal hydrolysis and its involvement of the tetrahedral intermediate was once somewhat contested. in this question you will fortify your understanding of this mechanistic pathway by exploring some of the data that led chemists to our current understanding of the reaction. a. Initially, many chemists assumed that once protonated, acetals undergo direct nucleophilic attack by water to expel one molecule of the alcohol, as shown below. Assuming this is the rate-limiting step of the reaction, write the rate law you would expect for this mechanistic version of the hydrolysis, and explain your logic in one sentence. (You may abbreviate the structure of the protonated acetal as "Intermediate A" in your rate law.) H Me rate- OMe limiting step? OMe :OH2 b. In reality, thanks to data gleaned from kinetics experiments, we now realize that direct nucleophilic attack is not the most reasonable or likely mechanistic pathway for acetal hydrolysis. Below is shown the actual rate- limiting step of acetal hydrolysis. Based on this information, write the corresponding rate law, and explain your logic in one sentence. (You may abbreviate the structure of the protonated acetal as "Intermediate B" in your rate law.) rate- limiting step :OMe OMe H. Ме c. A landmark study into the mechanism of acetal chemistry started with radiolabeled benzaldehyde, wherein the oxygen of the aldehyde was replaced with its heavier isotope oxygen-18 (180). The radiolabeled aldehyde was treated with non-radiolabeled n-butyl alcohol in the presence of strong acid catalyst as shown in the complete reaction equation shown below, without radiolabeling in the products. Based on your knowledge of the reaction mechanism, circle any oxygen atom(s) in the products shown that should be radiolabeled, and explain your logic in one sentence, 180 НО. + H20 H* cat.
Transcribed Image Text:6. Though we take it for granted nowadays, the mechanism of acetal hydrolysis and its involvement of the tetrahedral intermediate was once somewhat contested. in this question you will fortify your understanding of this mechanistic pathway by exploring some of the data that led chemists to our current understanding of the reaction. a. Initially, many chemists assumed that once protonated, acetals undergo direct nucleophilic attack by water to expel one molecule of the alcohol, as shown below. Assuming this is the rate-limiting step of the reaction, write the rate law you would expect for this mechanistic version of the hydrolysis, and explain your logic in one sentence. (You may abbreviate the structure of the protonated acetal as "Intermediate A" in your rate law.) H Me rate- OMe limiting step? OMe :OH2 b. In reality, thanks to data gleaned from kinetics experiments, we now realize that direct nucleophilic attack is not the most reasonable or likely mechanistic pathway for acetal hydrolysis. Below is shown the actual rate- limiting step of acetal hydrolysis. Based on this information, write the corresponding rate law, and explain your logic in one sentence. (You may abbreviate the structure of the protonated acetal as "Intermediate B" in your rate law.) rate- limiting step :OMe OMe H. Ме c. A landmark study into the mechanism of acetal chemistry started with radiolabeled benzaldehyde, wherein the oxygen of the aldehyde was replaced with its heavier isotope oxygen-18 (180). The radiolabeled aldehyde was treated with non-radiolabeled n-butyl alcohol in the presence of strong acid catalyst as shown in the complete reaction equation shown below, without radiolabeling in the products. Based on your knowledge of the reaction mechanism, circle any oxygen atom(s) in the products shown that should be radiolabeled, and explain your logic in one sentence, 180 НО. + H20 H* cat.
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