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CH3 NH3, H* H3C H3C CH `N' Substituted pyrroles are often prepared by treatment of a 1,4-diketone with ammonia in the presence of catalytic H*. The mechanism involves the following steps: 1) Protonation of the carbonyl oxygen and nucleophilic attack by ammonia form tetrahedral intermediate 1; 2) Proton transfer leads to protonated carbinolamine 2; 3) B-elimination leads to enamine 3; 4) Protonation of the carbonyl oxygen and nucleophilic attack by the amine form tetrahedral intermediate 4; 5) Proton transfer leads to protonated carbinolamine 5; 6) B-elimination leads to the final product. Write out the reaction mechanism on a separate sheet of paper, and then draw the structure of tetrahedral intermediate 4. You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer.

CH3 NH3, H* H3C H3C CH `N' Substituted pyrroles are often prepared by treatment of a 1,4-diketone with ammonia in the presence of catalytic H*. The mechanism involves the following steps: 1) Protonation of the carbonyl oxygen and nucleophilic attack by ammonia form tetrahedral intermediate 1; 2) Proton transfer leads to protonated carbinolamine 2; 3) B-elimination leads to enamine 3; 4) Protonation of the carbonyl oxygen and nucleophilic attack by the amine form tetrahedral intermediate 4; 5) Proton transfer leads to protonated carbinolamine 5; 6) B-elimination leads to the final product. Write out the reaction mechanism on a separate sheet of paper, and then draw the structure of tetrahedral intermediate 4. You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer.

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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CH3 NH3, H* H3C H3C CH: Substituted pyrroles are often prepared by treatment of a 1,4-diketone with ammonia in the presence of catalytic H*. The mechanism involves the following steps: 1) Protonation of the carbonyl oxygen and nucleophilic attack by ammonia form tetrahedral intermediate 1; 2) Proton transfer leads to protonated carbinolamine 2; 3) B-elimination leads to enamine 3; 4) Protonation of the carbonyl oxygen and nucleophilic attack by the amine form tetrahedral intermediate 4; 5) Proton transfer leads to protonated carbinolamine 5; 6) B-elimination leads to the final product. Write out the reaction mechanism on a separate sheet of paper, and then draw the structure of tetrahedral intermediate 4. • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. ZI
Transcribed Image Text:CH3 NH3, H* H3C H3C CH: Substituted pyrroles are often prepared by treatment of a 1,4-diketone with ammonia in the presence of catalytic H*. The mechanism involves the following steps: 1) Protonation of the carbonyl oxygen and nucleophilic attack by ammonia form tetrahedral intermediate 1; 2) Proton transfer leads to protonated carbinolamine 2; 3) B-elimination leads to enamine 3; 4) Protonation of the carbonyl oxygen and nucleophilic attack by the amine form tetrahedral intermediate 4; 5) Proton transfer leads to protonated carbinolamine 5; 6) B-elimination leads to the final product. Write out the reaction mechanism on a separate sheet of paper, and then draw the structure of tetrahedral intermediate 4. • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. ZI
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