# Is it possible to distinguish between cyclohexanol and cyclohex-2-en-1-ol with simple chemical test?

Primary, secondary and tertiary alcohols can easily be distinguished by using reagent tests such as:

• The triiodomethane test for $$\ce{R-CH(CH3)OH}$$ alcohols.
• Lucas' reagent to distinguish between three alcohol groups.
• A combination of reagents to distinguish between three alcohols. For example, dichromate to distinguish between tertiary and primary/secondary alcohols and subsequently Fehling's solution to distinguish between primary and secondary alcohols.

Would it be possible to distinguish between two secondary alcohols? For example, between cyclohexanol (1) and cyclohex-2-en-1-ol (2) using simple chemical tests?

• There are reagents like MnO2 which will selectively oxidise allylic alcohols, and can therefore act as a basis for chemically differentiating the above two compounds. I'm not sure that's what you are looking for, though? Are you looking for something that can be done quickly in a test tube in a high school-ish lab? – orthocresol Apr 23 at 22:30
• An alternate approach for this specific case would be Br2 reaction with the alkene – Andrew Apr 23 at 22:48
• Yes, it is possible to distinguish. – Desai Apr 23 at 22:56
• – Nilay Ghosh Apr 24 at 4:04