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.

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Write out the chemical reaction.

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.
CH3
CH
Ph
PhIl
PhIll
1
2.
Reaction:
Но
OH
H.
H-
H-
OH
(no stereochemistry
implied)
(cat.)
Transcribed Image Text: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. CH3 CH Ph PhIl PhIll 1 2. Reaction: Но OH H. H- H- OH (no stereochemistry implied) (cat.)
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