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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?

1: cyclohexanol; 2: cyclohex-2-en-1-ol

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    $\begingroup$ 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? $\endgroup$ – orthocresol Apr 23 at 22:30
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    $\begingroup$ An alternate approach for this specific case would be Br2 reaction with the alkene $\endgroup$ – Andrew Apr 23 at 22:48
  • $\begingroup$ Yes, it is possible to distinguish. $\endgroup$ – Desai Apr 23 at 22:56
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    $\begingroup$ Yes. Try Br2 in CCl4/KMnO4 in either acidic or alkaline medium/HBr $\endgroup$ – Nilay Ghosh Apr 24 at 4:04

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