Secondary alcohol oxidation
Oxidation removes hydrogen from the O-H group and its attached carbon, creating a C=O bond. Because that carbon already bonds to two other carbons, the product is a ketone and the six-membered ring is retained.
- Reagents
- Acidified dichromate(VI)
- Conditions
- Warm with oxidant
- Reaction class
- Secondary alcohol oxidation
- Equation
- C6H11OH + [O] -> C6H10O + H2O
Overview
Oxidation removes hydrogen from the O-H group and its attached carbon, creating a C=O bond. Because that carbon already bonds to two other carbons, the product is a ketone and the six-membered ring is retained.
Transformation
- Equation
- C6H11OH + [O] -> C6H10O + H2O
- Reagents
- Acidified dichromate(VI)
- Environment
- Warm with oxidant
- Reaction class
- Secondary alcohol oxidation
- Mechanism
- alcohol oxidation
- Evidence level
- source-backed molecular example
Scope and limitations
- Scope
- A secondary cyclic alcohol gives a cyclic ketone.
- Limitations
- Ordinary oxidation retains the ring; harsher oxidative cleavage is a different transformation.
Related reactions
- Dehydration: Cyclohexanol → Cyclohexene
Cyclohexanol gives cyclohexene through dehydration.
- Ketone reduction: Cyclohexanone → Cyclohexanol
Hydride adds to the planar carbonyl carbon while the pi electrons move onto oxygen. Subsequent protonation gives cyclohexanol; the existing carbon ring remains intact.
References
- Organic Chemistry: Oxidation of AlcoholsJohn McMurry · OpenStax Organic Chemistry · 2023
Supports functional-group chemistry used to curate the linked examples. Checked 2026-09-16; named examples are applications of textbook scope, without claimed experimental yields.