Formation of Acetals, the Acetonide of Hydrobenzoin Background The object of the present experiment is to demonstrate, using logic based on nuclear magnetic resonance (NMR) spectral data, whether the hydrobenzoin you start with is the meso or the racemic isomer. The 1,2-diphenyl-1,2-ethanediol (hydrobenzoin) is reacted with acetone to form a crystalline acetonide (a ketal) that will have either structure 1 or 2. Examination of the NMR spectrum of this derivative will reveal whether the two methyl groups of the acetonide are equivalent or not and thus whether the diol was meso or racemic. CH, CH Phl 2.

Formation of Acetals, the Acetonide of Hydrobenzoin Background The object of the present experiment is to demonstrate, using logic based on nuclear magnetic resonance (NMR) spectral data, whether the hydrobenzoin you start with is the meso or the racemic isomer. The 1,2-diphenyl-1,2-ethanediol (hydrobenzoin) is reacted with acetone to form a crystalline acetonide (a ketal) that will have either structure 1 or 2. Examination of the NMR spectrum of this derivative will reveal whether the two methyl groups of the acetonide are equivalent or not and thus whether the diol was meso or racemic. CH, CH Phl 2.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations

Section11.SE: Something Extra

Problem 79AP

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