July 03, 2020, 03:01:25 PM
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Topic: MENTALLY select the starting material in the box which would have the largest K  (Read 4492 times)

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Offline webassignbuddy

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


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

Offline discodermolide

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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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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.

Offline webassignbuddy

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I have 30 min to answer this question :'(

Offline webassignbuddy

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Is the answer this?

FC1CC=CCC1

Offline discodermolide

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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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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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Offline AlphaScent

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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?
If you're not part of the solution, then you're part of the precipitate

Offline AlphaScent

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Is that a guess?

Why might it be that is the most easily deprotonated?
If you're not part of the solution, then you're part of the precipitate

Offline webassignbuddy

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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.

Offline discodermolide

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Yes, more or less correct. I would go for that structure.
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Offline AlphaScent

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Great!! Hope you got it in!
If you're not part of the solution, then you're part of the precipitate

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