Chapter 17: Aldehydes and Ketones. Nucleophilic Addition to C=O |
Oxidation of Primary
and Secondary Alcohols
(review of Chapter 15)
Summary
Study Tip: If you see Cr reagents, you are probably looking at an oxidation reaction of a alcohol or an aldehyde. |
1o alcohol aldehyde |
2o alcohol ketone |
3o alcohol |
Cr OXIDATION OF ALCOHOLS |
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The mechanism is not trivial,
so attention here is focussed 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. |
QUESTIONS
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© Dr. Ian Hunt, Department of Chemistry |