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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: catsarecute02 on October 08, 2021, 04:53:52 PM

Title: pKa and Acid strength problem
Post by: catsarecute02 on October 08, 2021, 04:53:52 PM

so i'm thinking A because of my pKa numbers but it also might be B?!?

Title: Re: pKa and Acid strength problem
Post by: catsarecute02 on October 08, 2021, 04:54:29 PM

i might be getting my pKa numbers wrong...

Title: Re: pKa and Acid strength problem
Post by: Babcock_Hall on October 08, 2021, 05:10:17 PM

I think that your pK_a for Ph-NH₃⁺ is off a bit.  I am having a difficult time reading your pK_a for thiol groups.  In my experience they often fall in the range 8-10.

Title: Re: pKa and Acid strength problem
Post by: catsarecute02 on October 08, 2021, 05:19:43 PM

my thiol group has 10.6

but would the answer be A or B?

Title: Re: pKa and Acid strength problem
Post by: Babcock_Hall on October 08, 2021, 05:26:05 PM

What is the pK_a of acetone?  If you know this value, then you should be fine.

Title: Re: pKa and Acid strength problem
Post by: catsarecute02 on October 08, 2021, 05:40:22 PM

19.3 and i put 19 so my answer of A is correct?

Title: Re: pKa and Acid strength problem
Post by: Babcock_Hall on October 08, 2021, 06:07:33 PM

As far as I can tell, A has the correct order, but your pK_a value for the anilinium ion is wrong by a good six orders of magnitude.