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Topic: MENTALLY select the starting material in the box which would have the largest K  (Read 6782 times)

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Offline webassignbuddy

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MENTALLY select the starting material in the box which would have the largest K
« on: November 26, 2013, 11:58:23 AM »


 Draw only the deprotonated product and that WITHOUT any spectator ion.


I put in Fc1cc#ccc1 as my answer but got it wrong.
:(
Help?
 
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Offline discodermolide

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Re: MENTALLY select the starting material in the box which would have the largest K
« Reply #1 on: November 26, 2013, 12:02:04 PM »
In your answer you forgot the OH group!
So which compound will be the most acidic?
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Offline webassignbuddy

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Re: MENTALLY select the starting material in the box which would have the largest K
« Reply #2 on: November 26, 2013, 12:17:15 PM »
Quote from: discodermolide on November 26, 2013, 12:02:04 PM
In your answer you forgot the OH group!
So which compound will be the most acidic?

I was thinking the third one will be the most acidic. And OH leaves according the the diagram.
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Offline webassignbuddy

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Re: MENTALLY select the starting material in the box which would have the largest K
« Reply #3 on: November 26, 2013, 12:26:22 PM »
I have 30 min to answer this question :'(
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Offline webassignbuddy

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Re: MENTALLY select the starting material in the box which would have the largest K
« Reply #4 on: November 26, 2013, 12:33:34 PM »
Is the answer this?

FC1CC=CCC1
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Offline discodermolide

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Re: MENTALLY select the starting material in the box which would have the largest K
« Reply #5 on: November 26, 2013, 12:35:44 PM »
Well I do not understand your diagram, but I know that OH will not leave, you are being asked for de-protonation not de-hydroxylation!
And I do not agree that the third compound will be the most acidic.
Compare cyclohexanol to phenol in their reactions with OH-, which will be de-protonated faster?

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Offline discodermolide

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Re: MENTALLY select the starting material in the box which would have the largest K
« Reply #6 on: November 26, 2013, 12:36:30 PM »
Quote from: webassignbuddy on November 26, 2013, 12:33:34 PM
Is the answer this?

FC1CC=CCC1

No, that is not correct, see my previous post.
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Offline webassignbuddy

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Re: MENTALLY select the starting material in the box which would have the largest K
« Reply #7 on: November 26, 2013, 12:39:15 PM »
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Offline AlphaScent

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Re: MENTALLY select the starting material in the box which would have the largest K
« Reply #8 on: November 26, 2013, 12:39:48 PM »
I take it a half hour is up. 

Have you come to a conclusion?  Reasoned anything out as to why it is not the third compound?
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Offline AlphaScent

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Re: MENTALLY select the starting material in the box which would have the largest K
« Reply #9 on: November 26, 2013, 12:40:33 PM »
Is that a guess?

Why might it be that is the most easily deprotonated?
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Offline webassignbuddy

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Re: MENTALLY select the starting material in the box which would have the largest K
« Reply #10 on: November 26, 2013, 12:41:50 PM »
Quote from: AlphaScent on November 26, 2013, 12:40:33 PM
Is that a guess?

Why might it be that is the most easily deprotonated?

Because F is withdrawing electron density from the stable/electron rich benzene ring. Which causes electron denesity of the OH to be donated INTO the benzene ring to compensate. Thus making the O-H bond really thin and the H really acidic/very likely to be deprotonated.
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Offline discodermolide

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Re: MENTALLY select the starting material in the box which would have the largest K
« Reply #11 on: November 26, 2013, 12:48:20 PM »
Yes, more or less correct. I would go for that structure.
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Offline AlphaScent

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Re: MENTALLY select the starting material in the box which would have the largest K
« Reply #12 on: November 26, 2013, 04:05:31 PM »
Great!! Hope you got it in!
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