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Topic: gem diol to ketone mechanism  (Read 3028 times)

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Offline noork85

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gem diol to ketone mechanism
« on: May 19, 2013, 04:37:03 PM »

Offline TheOrganic

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Re: gem diol to ketone mechanism
« Reply #1 on: May 19, 2013, 05:07:05 PM »
Does this mechanism seem correct?

thanks

https://www.dropbox.com/s/atzvty6ibdbhotg/2013-05-19%2016.34.27.jpg

I think so. Why don't you try Google? It's often very helpful for standard reactions.

Offline noork85

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Re: gem diol to ketone mechanism
« Reply #2 on: May 19, 2013, 05:27:11 PM »
i did....but nothing on the mechanism...

thank you.

Offline Dan

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Re: gem diol to ketone mechanism
« Reply #3 on: May 19, 2013, 05:29:47 PM »
Does this mechanism seem correct?

I think it's fine. In the step where H2O is lost, it is more conventional to draw a curly arrow from the -OH lone pair kicking out water to give the protonated ketone directly (i.e. go directly from the second structure to the fourth in your answer). Since your third and fourth structures are resonance structures, your answer looks perfectly reasonable to me.

This mechanism is analogous to acetal hydrolysis - this mechanism is easily found via google or textbook.
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Offline noork85

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Re: gem diol to ketone mechanism
« Reply #4 on: May 19, 2013, 06:57:48 PM »
Does this mechanism seem correct?

I think it's fine. In the step where H2O is lost, it is more conventional to draw a curly arrow from the -OH lone pair kicking out water to give the protonated ketone directly (i.e. go directly from the second structure to the fourth in your answer). Since your third and fourth structures are resonance structures, your answer looks perfectly reasonable to me.

This mechanism is analogous to acetal hydrolysis - this mechanism is easily found via google or textbook.

i thought as much...thank you for confirming Dan. i just wanted to be sure because these are questions that can possibly appear on my exam.

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