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

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 28VC

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