Organic Chemistry

1

Ankur ·2009-11-01 21:23:37

I tried this question. Can you post figure of C?? I'm not so sure of my steps ( and more certainly, I'm wrong this time).
So, plz. post the figure of C.

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Ankur ·2009-11-01 21:32:23

Pritish, can you explain your first step? Reaction of cyclohexanone with Mg/ether ? From where you are using MgBr.?

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39

Pritish Chakraborty ·2009-11-01 21:58:36

Ankur how did you get that dimer? Mechanism bata, what I thought of is just a fluke!

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Ankur ·2009-11-01 22:03:34

nooo..... wait... guys wait.. I didn't solve that time by mechanism and that thing is wrong..I'm reposting.. wait..
And pritish, in which sense you are claiming it to be fluke?

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Ankur ·2009-11-01 22:11:42

Here is mechanism:
. The initial process is formation of pinacol and pinacol-pinacolene rearrangement proceeds.

So it should be the answer.

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Pritish Chakraborty ·2009-11-01 22:13:53

Yeah, I'm not so good in radical-anion mechanisms. I initially thought Mg would donate electrons to the carbonyl bond, but didn't think of dimerisation. Yours is more logical.