What organic product would you obtain from reaction of 1-pentanol with CrO3, H2O, H2SO4?

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
Chapter7: Alkynes
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Problem 7.27P: Following is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis...
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What organic product would you obtain from reaction of 1-pentanol with CrO3, H2O, H2SO4?

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Structure of  1-pentanol  is

CH3-CH2-CH2-CH2-CH2-OH which is a primary alcohol. 

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