Two students are given the starting material benzoic acid and are asked to prepare benzaldehyde. The first student starts by refluxing her sample of benzoic acid in thionyl chloride in the fume hood. Upon completion of the reaction, she evaporates the thionyl chloride to isolate compound A. She treats compound A with a stoichiometric amount of lithium tri-tert-butoxyaluminum hydride at -78 °C in diethyl ether, producing compound B. Adding water, she isolates her product, compound C. The second student takes a different route. She treats benzoic acid with an excess of lithium aluminum hydride (LAH) in diethyl ether, followed by careful addition of ethyl acetate to remove any unreacted LAH. She adds water and isolates her product, compound D. Draw the structure for compound A, compound C, and compound D.

Two students are given the starting material benzoic acid and are asked to prepare benzaldehyde. The first student starts by refluxing her sample of benzoic acid in thionyl chloride in the fume hood. Upon completion of the reaction, she evaporates the thionyl chloride to isolate compound A. She treats compound A with a stoichiometric amount of lithium tri-tert-butoxyaluminum hydride at -78 °C in diethyl ether, producing compound B. Adding water, she isolates her product, compound C. The second student takes a different route. She treats benzoic acid with an excess of lithium aluminum hydride (LAH) in diethyl ether, followed by careful addition of ethyl acetate to remove any unreacted LAH. She adds water and isolates her product, compound D. Draw the structure for compound A, compound C, and compound D.

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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