Unknown Organic Chemicals Distinction

[scurry18]

1. The problem statement, all variables and given/known data
Use a flow chart to distinguish between: 1-hexene, cyclohexanol, 1-bromobutane, 1-propanol, 2-hexene, 1-hexyne, 2-bromopentane, 3-methyl-3-hexanol, 3-bromo-3-methylhexane by using a positive and negative test by adding other compounds


2. Relevant equations
N/A


3. The attempt at a solution
I used ZnCl2 in HCl to distinguish cyclohexanol and 3-methyl-3-hexanol from the rest and used the same test to distinguish them from each other.
Then, I used acidic chromate solution to distinguish 1-propanol by the formation of green chromium (III) ion
I just do not know where to find the information on how to separate these compounds (It is not in my book.) Any and all information would be awesome!

[chemisttree]

I just do not know where to find the information on how to separate these compounds (It is not in my book.) Any and all information would be awesome!

Is the question asking to distinguish between samples of each of these or to find a way to separate a mixture of them?

[scurry18]

It asks to distinguish between different samples of each. They are NOT mixed together.

[chemisttree]

Separate them into groups. You have 3 examples of alcohols, one primary, one secondary and one tertiary. You have 2 examples of olefins, one alpha and one internal. You have one example of an alkyne. Its unsaturation might lead you to believe that it is an olefin but it has a property that olefins don't. You have 3 examples of alkyl halides, one primary, one secondary and one tertiary.

Now, find some tests to distinguish between them (http://www.docbrown.info/page13/ChemicalTests/ChemicalTests.htm) and you are ready to begin.