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Topic: CN- ions  (Read 2351 times)

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Offline greentea11

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CN- ions
« on: March 11, 2014, 07:25:11 PM »
For the attached reaction, the only reagent given is CN- ions. So they must act as a catalyst, so I thought benzoin reaction/condensation, however I cannot reach the correct product from this

I then thought 1,4 addition to second reactant to remove the double bond

not sure what route to go with for this, just can't seem to get the product, any hints?

Offline Babcock_Hall

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Re: CN- ions
« Reply #1 on: March 11, 2014, 07:29:33 PM »
Is there any chance that you missed a "Ph" group in your product?

Offline greentea11

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Re: CN- ions
« Reply #2 on: March 11, 2014, 07:30:45 PM »
yes! oops
should be on the carbon adjacent to the first carbonyl group

Offline Babcock_Hall

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Re: CN- ions
« Reply #3 on: March 12, 2014, 10:02:57 AM »
Now it should be more straightforward how to get to the product.

Offline greentea11

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Re: CN- ions
« Reply #4 on: March 12, 2014, 10:36:24 AM »
I can't see how to do it though, my benzoin condensation doesn't bring the correct product? I don't know how to attach the the reactants at the carbon they form the product, by only using CN-?

Edit: think I got it

Offline zsinger

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Re: CN- ions
« Reply #5 on: March 15, 2014, 07:32:03 PM »
Try a PTC (Phase Transfer Catalyst).  CN- is, indeed, a nucleophile. :o
« Last Edit: March 15, 2014, 07:42:17 PM by zsinger »
"The answer is of zero significance if one cannot distinctly arrive at said place with an explanation"

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