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Chapter 15: Alcohols, Diols and Thiols



Overview | Reaction of Alcohols with Hydrogen Halides | Reaction with SOCL2, PX3 to give Alkyl Halides | Acid catalyzed Dehydration | Synthesis of Ethers | Synthesis of Esters | Oxidation | Cleavage of 1,2-Diols |


Oxidation of Alcohols

Chapter 15: Alcohols, Diols and Thiols

Oxidation of Alcohols

general scheme for the oxidation of alcohols
Reaction type: Oxidation-Reduction

Summary

reagents for the oxidation of alcohols
oxidation of RCH2OH
oxidation of R2CHOH
oxidation of R3COH


Cr OXIDATION OF ALCOHOLS
The mechanism is not trivial, so attention here is focused on the actual oxidation step. Prior to this, the alcohol reacts to form a chromate ester (shown). A base (here a water molecule) abstracts a proton from the chromate ester, the C=O forms and a Cr species leaves.
This demonstrates the importance of the carbinol H to this mechanism.
oxidation of alcohols
Questions:
What type of reaction could the oxidation step be decribed as ? an elimination, specifically an E2
What is the oxidation state of Cr in chromic acid ? H2CrO4 = Cr VI
What is the oxidation state of the Cr in the chromate ester intermediate ? still Cr VI
What is the oxidation state of the Cr in the "leaving group", HCrO3- Cr IV

Study Tip: If you see Cr reagents, you are probably looking at an oxidation reaction.


 


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