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Topic: enolester as caboxylic acid?  (Read 11820 times)

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Offline taurean

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enolester as caboxylic acid?
« on: December 21, 2007, 09:02:20 PM »
Can a enolester be considered equivalent to carboxylic acid?  If so, why?

Could someone please answer?

Thanks,
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Offline taurean

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Re: enolester as caboxylic acid?
« Reply #1 on: December 23, 2007, 01:13:12 PM »
Could someone please answer?
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Offline Mitch

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Re: enolester as caboxylic acid?
« Reply #2 on: December 23, 2007, 01:41:54 PM »
equivalent in what way?
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Offline taurean

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Re: enolester as caboxylic acid?
« Reply #3 on: December 23, 2007, 03:28:47 PM »
Quote from: Mitch on December 23, 2007, 01:41:54 PM
equivalent in what way?

in terms of reactivity.
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Offline Mitch

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Re: enolester as caboxylic acid?
« Reply #4 on: December 23, 2007, 03:36:18 PM »
Would you expect the pka to be anywhere near equivalent?
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Offline taurean

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Re: enolester as caboxylic acid?
« Reply #5 on: December 23, 2007, 04:36:21 PM »
Quote from: Mitch on December 23, 2007, 03:36:18 PM
Would you expect the pka to be anywhere near equivalent?

Yes, they are almost same (~11)
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Offline Borek

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Re: enolester as caboxylic acid?
« Reply #6 on: December 23, 2007, 04:59:55 PM »
What is enolester? Something like ...C=C(O)C(=O)O... ? Or other way around?
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Offline taurean

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Re: enolester as caboxylic acid?
« Reply #7 on: December 23, 2007, 05:09:19 PM »
Quote from: Borek on December 23, 2007, 04:59:55 PM
What is enolester? Something like ...C=C(O)C(=O)O... ? Or other way around?

enol of a beta ketoester
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Offline agrobert

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Re: enolester as caboxylic acid?
« Reply #8 on: December 23, 2007, 05:23:44 PM »
In terms of reactivity how?  Do you mean could you perform similar synthetic transformations?  The enol hydrogen is acidic but what about the alpha carbon?  What to you want to achieve?
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Offline taurean

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Re: enolester as caboxylic acid?
« Reply #9 on: December 23, 2007, 05:31:14 PM »
Quote from: agrobert on December 23, 2007, 05:23:44 PM
In terms of reactivity how?  Do you mean could you perform similar synthetic transformations?  The enol hydrogen is acidic but what about the alpha carbon?  What to you want to achieve?

Borane would react with carboxylic acids.  Would it react with this kind of enol too?
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Offline Borek

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Re: enolester as caboxylic acid?
« Reply #10 on: December 23, 2007, 06:13:49 PM »
beta... so more like ...C(O)=C*C(=O)O... But if so, won't acidity of the compound depend on the way * carbon is substituted?

Or is my orgo so rusty I am completely wrong?
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Offline agrobert

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Re: enolester as caboxylic acid?
« Reply #11 on: December 23, 2007, 07:00:47 PM »
I think the structure is

RC(OH)=CH-O-R
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Offline Borek

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Re: enolester as caboxylic acid?
« Reply #12 on: December 23, 2007, 07:08:25 PM »
Quote from: agrobert on December 23, 2007, 07:00:47 PM
I think the structure is

RC(OH)=CH-O-R

Seems like enolether, not ester to me.
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Offline taurean

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Re: enolester as caboxylic acid?
« Reply #13 on: December 23, 2007, 10:19:11 PM »
Quote from: Borek on December 23, 2007, 07:08:25 PM
Quote from: agrobert on December 23, 2007, 07:00:47 PM
I think the structure is

RC(OH)=CH-O-R

Seems like enolether, not ester to me.

The structure is R-C(OH)=CH-CO2Et
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Offline macman104

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Re: enolester as caboxylic acid?
« Reply #14 on: December 23, 2007, 10:29:09 PM »
If you could clarify just a little bit, what carboxylic acid would you compare this enol-ester with (since you are asking about equivalency)?  I think that will help eliminate the confusion that seems to be going on here.  So, you want to compare R-C(OH)=CH-C(=O)-OEt with...____________ (fill in your carboxylic acid)

Basically, I'm trying to eliminate whether the enol part of your question is important.  Are you asking if an ester can be functionally equivalent to a carboxylic acid?
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