When warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration and rearrangement to give 2-phenylpropanal. OH H H,SO, + H2O ОН 1-Phenyl-1,2-propanediol (racemic) 2-Phenylpropanal (racemic)

When warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration and rearrangement to give 2-phenylpropanal. OH H H,SO, + H2O ОН 1-Phenyl-1,2-propanediol (racemic) 2-Phenylpropanal (racemic)

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section20.6: Sigmatropic Shifts

Problem 20.12P

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Question

Account for the fact that 2-phenylpropanal is formed rather than its constitutional isomer, 1-phenyl-1-propanone.

When warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration
and rearrangement to give 2-phenylpropanal.
OH
H
H,SO,
+ H2O
ОН
1-Phenyl-1,2-propanediol
(racemic)
2-Phenylpropanal
(racemic)

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