Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 13, Problem 53P

A standard synthetic sequence for building a six-membered cyclic ketone onto an existing

aromatic ring is shown in outline as follows. Specify the reagents necessary for each step.

Chapter 13, Problem 53P, A standard synthetic sequence for building a six-membered cyclic ketone onto an existing aromatic

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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
Substitutions on aromatic rings are generally carried out by electrophilic substitution, but for the synthesis of phenolic compounds and alkoxy benzene it is carried out by nucleophilic substitution, explain why this is so .
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Organic Chemistry - Standalone book

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