4.) Propylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol, another chiral molecule: hydrolysis CH3 H,C HO a. Provide a mechanism for the acid-catalyzed hydrolysis of pure (R)-propylene oxide (treatment with H2SO4/H;O), showing the correct stereochemistry.

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
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.26P: Wittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and...
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4.) Propylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol,
another chiral molecule:
hydrolysis
CH3
H,C
HO
a. Provide a mechanism for the acid-catalyzed hydrolysis of pure (R)-propylene oxide (treatment
with H;SO4/H;O), showing the correct stereochemistry.
b. Provide a mechanism for the treatment of pure (R)-propylene oxide with NaOH in water
(base-catalyzed hydrolysis), showing the correct stereochemistry.
c. Explain why acid-catalyzed hydrolysis of optically active propylene oxide gives a product with
a rotation in the opposite direction from the product of the base catalyzed hydrolysis.
Transcribed Image Text:4.) Propylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol, another chiral molecule: hydrolysis CH3 H,C HO a. Provide a mechanism for the acid-catalyzed hydrolysis of pure (R)-propylene oxide (treatment with H;SO4/H;O), showing the correct stereochemistry. b. Provide a mechanism for the treatment of pure (R)-propylene oxide with NaOH in water (base-catalyzed hydrolysis), showing the correct stereochemistry. c. Explain why acid-catalyzed hydrolysis of optically active propylene oxide gives a product with a rotation in the opposite direction from the product of the base catalyzed hydrolysis.
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