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On the basis of the general mechanism for amide hydrolysis in acidic solution shown in Mechanism 20.4, write an analogous sequence of steps for the hydrolysis of acetanilide.

On the basis of the general mechanism for amide hydrolysis in acidic solution shown in Mechanism 20.4, write an analogous sequence of steps for the hydrolysis of acetanilide.

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
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On the basis of the general mechanism for amide hydrolysis in acidic solution shown in Mechanism 20.4, write an analogous sequence of steps for the hydrolysis of acetanilide. 

Amide Hydrolysis in Acid Solution THE OVERALL REACTION: H;O* NH, `NH2 R HO. An amide Hydronium ion A carboxylic acid Ammonium ion THE MECHANISM: First Stage: Formation of the tetrahedral intermediate Steps 1–3 are analogous to the mechanism of acid-catalyzed hydration of aldehydes and ketones and acid- catalyzed hydrolysis of esters. Step 1: Protonation of the carbonyl oxygen of the amide +ö-t H fast +. HTO: :0: NH2 `NH2 R H. H Amide Hydronium ion Protonated amide Water Step 2: Nucleophilic addition of water to the protonated amide HÖ: 0- H slow R NH2 R `NH2 H Protonated Water Conjugate acid of tetrahedral intermediate (TI-H) amide Step 3: Deprotonation of TI-H* to give the neutral form of the tetrahedral intermediate (TI) H HÖ: 0 H HÖ: :ÖH H fast :0: H-0: R NH2 R NH2 Conjugate acid of Water Tetrahedral Hydronium ion tetrahedral intermediate 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 elimination of ammonia or an amine from TI and restoration of the carbonyl group. Step 4: Protonation of TI at its amino nitrogen HÖ: ÖH H HÖ: ÖH fast R NH2 R NH3 Tetrahedral Hydronium ion Conjugate acid of Water intermediate (TI) tetrahedral intermediate (TI-H")
Transcribed Image Text:Amide Hydrolysis in Acid Solution THE OVERALL REACTION: H;O* NH, `NH2 R HO. An amide Hydronium ion A carboxylic acid Ammonium ion THE MECHANISM: First Stage: Formation of the tetrahedral intermediate Steps 1–3 are analogous to the mechanism of acid-catalyzed hydration of aldehydes and ketones and acid- catalyzed hydrolysis of esters. Step 1: Protonation of the carbonyl oxygen of the amide +ö-t H fast +. HTO: :0: NH2 `NH2 R H. H Amide Hydronium ion Protonated amide Water Step 2: Nucleophilic addition of water to the protonated amide HÖ: 0- H slow R NH2 R `NH2 H Protonated Water Conjugate acid of tetrahedral intermediate (TI-H) amide Step 3: Deprotonation of TI-H* to give the neutral form of the tetrahedral intermediate (TI) H HÖ: 0 H HÖ: :ÖH H fast :0: H-0: R NH2 R NH2 Conjugate acid of Water Tetrahedral Hydronium ion tetrahedral intermediate 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 elimination of ammonia or an amine from TI and restoration of the carbonyl group. Step 4: Protonation of TI at its amino nitrogen HÖ: ÖH H HÖ: ÖH fast R NH2 R NH3 Tetrahedral Hydronium ion Conjugate acid of Water intermediate (TI) tetrahedral intermediate (TI-H")
сontinued Step 5: Dissociation of the N-protonated form of the tetrahedral intermediate to give ammonia and the protonated form of the carboxylic acid H HÖ: ö-H slow :NH3 RCNH, R Conjugate acid of tetrahedral intermediate Protonated Ammonia carboxylic acid (TI-H*) Step 6: Proton-transfer processes give the carboxylic acid and ammonium ion :ö H fast :o: + H-o: R R H H. Protonated Water Carboxylic acid Hydronium carboxylic acid ion H H fast `:NH3 :0: H-NH, H H. Hydronium ion Ammonia Water Ammonium ion
Transcribed Image Text:сontinued Step 5: Dissociation of the N-protonated form of the tetrahedral intermediate to give ammonia and the protonated form of the carboxylic acid H HÖ: ö-H slow :NH3 RCNH, R Conjugate acid of tetrahedral intermediate Protonated Ammonia carboxylic acid (TI-H*) Step 6: Proton-transfer processes give the carboxylic acid and ammonium ion :ö H fast :o: + H-o: R R H H. Protonated Water Carboxylic acid Hydronium carboxylic acid ion H H fast `:NH3 :0: H-NH, H H. Hydronium ion Ammonia Water Ammonium ion
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