Can you draw out the following reaction mechanism: 1. Benzyl alcohol + H2SO4 → Benzyl oxonium ion + HSO4

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
Section21.SE: Something Extra
Problem 54AP: The following reactivity order has been found for the saponification of alkyl acetates by aqueous...
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Can you draw out the following reaction mechanism:

1. Benzyl alcohol + H2SO4 → Benzyl oxonium ion + HSO4-

2. Benzyl oxonium ion + CrO3 → Chromate ester

3. Chromate ester → Benzylic carbocation

4. Benzylic carbocation + H2O → Benzaldehyde + H3O+

5. Benzyl alcohol + H2CrO4 → Benzaldehyde + Cr3+ + 3H2SO4

Byproduct:

CrO3 + 3 H2O --> Cr3+ + 3 H2SO4

 

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