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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: webassignbuddy on November 26, 2013, 11:58:23 AM

Title: MENTALLY select the starting material in the box which would have the largest K
Post by: webassignbuddy on November 26, 2013, 11:58:23 AM: (https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fwww.webassign.net%2Fuserimages%2Fkasandbe%40ncsu%2FCH223_fall_02%2F223fall10_HW23_1.gif&hash=d2b429cdd367ae0f119ea533b8ba358dba711030)

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

I put in as my answer but got it wrong.
:(
Help?
Title: Re: MENTALLY select the starting material in the box which would have the largest K
Post by: 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?
Title: Re: MENTALLY select the starting material in the box which would have the largest K
Post by: webassignbuddy 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.
Title: Re: MENTALLY select the starting material in the box which would have the largest K
Post by: webassignbuddy on November 26, 2013, 12:26:22 PM: I have 30 min to answer this question :'(
Title: Re: MENTALLY select the starting material in the box which would have the largest K
Post by: webassignbuddy on November 26, 2013, 12:33:34 PM: Is the answer this?
Title: Re: MENTALLY select the starting material in the box which would have the largest K
Post by: discodermolide 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?
Title: Re: MENTALLY select the starting material in the box which would have the largest K
Post by: discodermolide on November 26, 2013, 12:36:30 PM: Quote from: webassignbuddy on November 26, 2013, 12:33:34 PM
Is the answer this?

No, that is not correct, see my previous post.
Title: Re: MENTALLY select the starting material in the box which would have the largest K
Post by: webassignbuddy on November 26, 2013, 12:39:15 PM: Quote from: discodermolide on November 26, 2013, 12:36:30 PM
Quote from: webassignbuddy on November 26, 2013, 12:33:34 PM
Is the answer this?

No, that is not correct, see my previous post.
Title: Re: MENTALLY select the starting material in the box which would have the largest K
Post by: AlphaScent 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?
Title: Re: MENTALLY select the starting material in the box which would have the largest K
Post by: AlphaScent on November 26, 2013, 12:40:33 PM: Is that a guess?

Why might it be that is the most easily deprotonated?
Title: Re: MENTALLY select the starting material in the box which would have the largest K
Post by: webassignbuddy 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.
Title: Re: MENTALLY select the starting material in the box which would have the largest K
Post by: discodermolide on November 26, 2013, 12:48:20 PM: Yes, more or less correct. I would go for that structure.
Title: Re: MENTALLY select the starting material in the box which would have the largest K
Post by: AlphaScent on November 26, 2013, 04:05:31 PM: Great!! Hope you got it in!