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    1.) Suggest a chemical test that would allow you to distinguish between tert-butyl alcohol and 1 butanol, both of which give a positive ceric nitrate test?

    2.) Why are axial and equatorial hydroxyl isomers for 4 tert butylcyclohexanone, but not for cyclohexanol itself? ( I was thinking steric factors?)

    3.) I have to balance this:

    O OH
    = -
    C-C-C-C-C-C + NaBH4 ---> C-C-C-C-C-C

    so basically its a 6 carbon chain, and on the 4th carbon there is a double bond on the "oxygen" plus NaBH4 yields another 6 carbon chain with a OH on the fourth carbon.

    4.) 2-Pentanol, the product, has a asymmetric carbon as a result of the reduction. A solution of the product shows no optical rotation. Explain this observation in full, showing the mechanism of the reaction

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    Dr. Richard Musgrave (105813)

    1.) Suggest a chemical test that would allow you to distinguish between tert-butyl alcohol and 1 butanol, both of which give a positive ceric nitrate test?
    A good test here is the chromic acid (chromic anhydride) test. Tert-butyl alcohol will not react, while 1-butanol will react to form a carboxylic acid and the Cr3+ ion which turn the solution into a blue-green color.
    (Please see the attached file)
    T-butyl alcohol has no ...

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