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On the basis of the general mechanism for acid-catalyzed ester hydrolysis shown in Mechanism 20.2, write an analogous sequence of steps for the specific case of ethyl benzoate hydrolysis.

On the basis of the general mechanism for acid-catalyzed ester hydrolysis shown in Mechanism 20.2, write an analogous sequence of steps for the specific case of ethyl benzoate hydrolysis.

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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
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On the basis of the general mechanism for acid-catalyzed ester hydrolysis shown in Mechanism 20.2, write an analogous sequence of steps for the specific case of ethyl benzoate hydrolysis.

Step 2: Nucleophilic addition of water to the protonated ester H HÖ: 0,-H H slow R ÖCH; R ÖCH; H Conjugate acid of tetrahedral intermediate (T-H") Protonated ester Water Step 3: Deprotonation of TI-H* to give the neutral form of the tetrahedral intermediate (TI) H HÖ: 0H- HÖ: ÖH H H fast H-Ö: R ÖCH3 ÖCH3 R H H Conjugate acid of tetrahedral intermediate Water Tetrahedral Hydronium ion intermediate (TI) (TI-H") Second Stage: Dissociation of the tetrahedral intermediate Just as steps 1-3 corresponded to addition of water to the carbonyl group, steps 4-6 correspond to climination of an alcohol, in this case methanol, from the TỈ and a restoration of the carbonyl group. Step 4: Protonation of the alkoxy oxygen of the tetrahedral intermediate HÖ: ÖH HÖ: ÖH H H fast HTO: :O: R OCH; R H H CH3 Tetrahedral Hydronium ion Conjugate acid of Water intermediate (TI) tetrahedral intermediate (TI-H") Step 5: Dissociation of the protonated form of the tetrahedral intermediate gives the alcohol and the protonated form of the carboxylic acid HÖ: ö- H H slow н + :0: R CH3 CH3 Conjugate acid of tetrahedral intermediate Protonated Methanol carboxylie acid (T-H") Step 6: Deprotonation of the protonated carboxylic acid completes the process H H fast :o: H-O: R O: H H Protonated Water Carboxylic acid Hydronium carboxylic acid ion
Transcribed Image Text:Step 2: Nucleophilic addition of water to the protonated ester H HÖ: 0,-H H slow R ÖCH; R ÖCH; H Conjugate acid of tetrahedral intermediate (T-H") Protonated ester Water Step 3: Deprotonation of TI-H* to give the neutral form of the tetrahedral intermediate (TI) H HÖ: 0H- HÖ: ÖH H H fast H-Ö: R ÖCH3 ÖCH3 R H H Conjugate acid of tetrahedral intermediate Water Tetrahedral Hydronium ion intermediate (TI) (TI-H") Second Stage: Dissociation of the tetrahedral intermediate Just as steps 1-3 corresponded to addition of water to the carbonyl group, steps 4-6 correspond to climination of an alcohol, in this case methanol, from the TỈ and a restoration of the carbonyl group. Step 4: Protonation of the alkoxy oxygen of the tetrahedral intermediate HÖ: ÖH HÖ: ÖH H H fast HTO: :O: R OCH; R H H CH3 Tetrahedral Hydronium ion Conjugate acid of Water intermediate (TI) tetrahedral intermediate (TI-H") Step 5: Dissociation of the protonated form of the tetrahedral intermediate gives the alcohol and the protonated form of the carboxylic acid HÖ: ö- H H slow н + :0: R CH3 CH3 Conjugate acid of tetrahedral intermediate Protonated Methanol carboxylie acid (T-H") Step 6: Deprotonation of the protonated carboxylic acid completes the process H H fast :o: H-O: R O: H H Protonated Water Carboxylic acid Hydronium carboxylic acid ion
Mechanism 20.2 Acid-Catalyzed Ester Hydrolysis THE OVERALL REACTION: H;O* H,0 CH;OH R OCH3 R HO Water А carboxylic A methyl Methanol ester acid THE MECHANISM: First Stage: Formation of the tetrahedral intermediate Steps 1–3 are analogous to the mechanism of acid-catalyzed hydration of an aldehyde or ketone. Step 1: Protonation of the carbonyl oxygen of the ester H +ö-H fast :0: OCH3 OCH3 R R. Methyl ester Hydronium ion Protonated ester Water
Transcribed Image Text:Mechanism 20.2 Acid-Catalyzed Ester Hydrolysis THE OVERALL REACTION: H;O* H,0 CH;OH R OCH3 R HO Water А carboxylic A methyl Methanol ester acid THE MECHANISM: First Stage: Formation of the tetrahedral intermediate Steps 1–3 are analogous to the mechanism of acid-catalyzed hydration of an aldehyde or ketone. Step 1: Protonation of the carbonyl oxygen of the ester H +ö-H fast :0: OCH3 OCH3 R R. Methyl ester Hydronium ion Protonated ester Water
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