The two reactions that follow involve nucleophilic substitution at an acyl carbon. For each reaction, show the electrophile and the nucleophile in the key bond- forming step, the corresponding tetrahedral addition intermediate, and the leaving group in the bond-breaking step. Write a general mechanistic scheme (use curved arrows to show bond-making and bond-breaking processes) for these reactions, keeping in mind that acid- and base-catalyzed processes will differ in their timing of proton transfers. 00 PhCOCPh+ C₂H5OH 00 PhCOCPh+ 2 CH3NH H₂SO4 cat. O PhCOC₂H5+ PhCO₂H PhCNCHg + CH3NH; PhCO

The two reactions that follow involve nucleophilic substitution at an acyl carbon. For each reaction, show the electrophile and the nucleophile in the key bond- forming step, the corresponding tetrahedral addition intermediate, and the leaving group in the bond-breaking step. Write a general mechanistic scheme (use curved arrows to show bond-making and bond-breaking processes) for these reactions, keeping in mind that acid- and base-catalyzed processes will differ in their timing of proton transfers. 00 PhCOCPh+ C₂H5OH 00 PhCOCPh+ 2 CH3NH H₂SO4 cat. O PhCOC₂H5+ PhCO₂H PhCNCHg + CH3NH; PhCO

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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Question

The two reactions that follow involve nucleophilic substitution at an acyl carbon.
For each reaction, show the electrophile and the nucleophile in the key bond-
forming step, the corresponding tetrahedral addition intermediate, and the leaving
group in the bond-breaking step. Write a general mechanistic scheme (use curved
arrows to show bond-making and bond-breaking processes) for these reactions,
keeping in mind that acid- and base-catalyzed processes will differ in their timing
of proton transfers.
00
|| ||
PhCOCPh+ C₂H5OH
00
||||
PhCOCPh+ 2 CH3NH
H₂SO4 cat.
O
PhCOC₂H5+ PhCO₂H
PhCNCHg + CH3NH PhCO

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