making diol from alkene?

[Verduchi]

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When making a diol group from an alkene the addition of the two hydroxyl groups is considered an oxidation or addition reaction?

 

[kein]

As far as I know, one doesn't rule out the other. Pretty sure it's both.

 

[YoAyDri]

Yes they are not mutually exclusive. Both are occurring in that reaction. But if I were explaining it, I would use the term oxidation of an alkene to produce a diol before I said addition of two hydroxyl groups.

 

[Verduchi]

This question was on september pcat it was a cyclohexene ring undergoing KMNO4 and asked which type of reaction it was.

 

[ciestar]

Pretty sure if it's involving KMNO4 it's an oxidation reaction since KMNO4 fully oxidizes alkenes (if I remember correctly)

 

[pharmerjohn]

Pretty sure if it's involving KMNO4 it's an oxidation reaction since KMNO4 fully oxidizes alkenes (if I remember correctly)

You're correct. Depending on the starting material, the product could be either ketone and/or aldehyde.

 

[YoAyDri]

You're correct. Depending on the starting material, the product could be either ketone and/or aldehyde.

If the starting material is a secondary alcohol, fully oxidized product would be ketone. Primary alcohol fully oxidized would be a carboxylic acid. You can use a reagent such as Dess Martin Periodane to partially oxidize a primary alcohol to aldehyde

 

[pharmerjohn]

Good call. It would form carboxylic acid or ketone. Thanks for pointing that out. 🙂

 

[YoAyDri]

Good call. It would form carboxylic acid or ketone. Thanks for pointing that out. 🙂

No problem...i enjoy synthesis. Cheers.

 

[Verduchi]

Yes they are not mutually exclusive. Both are occurring in that reaction. But if I were explaining it, I would use the term oxidation of an alkene to produce a diol before I said addition of two hydroxyl groups.

Thanks for explaining that.

 

[Verduchi]

Confirmed oxidation reaction via Dr.Collins July update. Don't know how I missed this one.