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conversion question

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beech167:
I need to convert 2-methylpropane to 2-methyl-1-propanol.  I think that this problem can be done in one step. But, what i'm not sure of is how you know exactly what you would add to it to give you the answer.  I know for example cyclopentane plus Cl2 gives you cyclopentyl chloride. Thats an easy example but on a more difficult problem how would you know to use Cl2

GCT:
Any one step solution would require oxidation, however, I am not too familiar with this process.  A mild oxidizing reagent would be required...potassium chromate?

In any case, here's another proposal:

Use diatomic chlorine in the presence of uv light, to generate a reaction where the 2-methyl-propane will become a secondary radical (the radical on the most stable, secondary carbon).  After the reaction has stabilized.

Now think of a way to transform the halide to the alcohol; should be easy enough.

AWK:
There is no secondary carbon atom in 2-methyl propane (isobutane).
But of course, there is possibility to eliminate HCl from t-butyl chloride, and after addition borane
and oxidation the needed alcohol can be obtained.

GCT:
Of course there is a secondary carbon in isobutane.

However, I was wrong in my proposing the secondary radical intermediate.  No such reaction takes place, I had it confused with the reaction chlorine radical with an alkene.  


--- Quote ---But of course, there is possibility to eliminate HCl from t-butyl chloride, and after addition borane
and oxidation the needed alcohol can be obtained.
--- End quote ---

The whole question was regarding the details on how such a reaction would bee formed inn the first place.  All I can think of at this moment is to react diatomic chlorine, uv, and the suggested isobutane.  Reaction with diatomic bromine would result in higher yield, however, chlorine, being nonselective would result in the statistical result, that is abstract one of the 9 hydrogen atoms.

mechanism
http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch04radical.html

Elimination of such a secondary halide does produce satisfactory yields, SN2 reactions, among others can take place.  

Substitution of the halide would be the best, two step mechanism (as opposed to three).  However, I'm not arriving at any ideas.

ximik:

--- Quote from: GCT on June 19, 2004, 03:02:59 PM ---Of course there is a secondary carbon in isobutane.

--- End quote ---

can you show where.

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