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Topic: alcohol seems like an acid, but it isn't  (Read 3739 times)

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Offline Palladipeloarancione

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alcohol seems like an acid, but it isn't
« on: April 11, 2013, 05:02:38 AM »
In acid a H+ proton is given from a molecule.
So organics acid are like this R-COOH, associated with their carboxyl group –COOH

Alcohol are like this R-OH.

It seems to me that the same OH bound would behave in the same way, and alcohol should be and acid too.
Obviously isn't so,
but why?

Thanks.

Andrea

Offline sjb

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Re: alcohol seems like an acid, but it isn't
« Reply #1 on: April 11, 2013, 05:09:30 AM »
In acid a H+ proton is given from a molecule.
So organics acid are like this R-COOH, associated with their carboxyl group –COOH

Alcohol are like this R-OH.

It seems to me that the same OH bound would behave in the same way, and alcohol should be and acid too.
Obviously isn't so,
but why?

Thanks.

Andrea

Why do you feel that the alcohol does not react as an acid?

Offline orgopete

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Re: alcohol seems like an acid, but it isn't
« Reply #2 on: April 11, 2013, 08:11:54 AM »
In acid a H+ proton is given from a molecule.
So organics acid are like this R-COOH, associated with their carboxyl group –COOH

Alcohol are like this R-OH.

It seems to me that the same OH bound would behave in the same way, and alcohol should be and acid too.


That is correct, qualitatively. However, quantitatively they do not lose a proton at the same rate. The degree to which R pulls electrons toward itself and away from the H, the easier an H(+) can form.

Alcohol can and do lose their proton, but only in more basic solutions than carboxylic acids.
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Offline Arkcon

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Re: alcohol seems like an acid, but it isn't
« Reply #3 on: April 11, 2013, 08:49:03 AM »
In acid a H+ proton is given from a molecule.
So organics acid are like this R-COOH, associated with their carboxyl group –COOH

Alcohol are like this R-OH.

It seems to me that the same OH bound would behave in the same way, and alcohol should be and acid too.


So the double bonded oxygen, with 4 unpaired electrons, sharing the carbon with the -OH group in the carboxylic acid, shouldn't be having any effect?  Such things are very important to understanding organic chemistry.
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

Offline Palladipeloarancione

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Re: alcohol seems like an acid, but it isn't
« Reply #4 on: April 16, 2013, 10:48:52 AM »
Why do you feel that the alcohol does not react as an acid?

Because mine is only a theoretical chemistry  ;D

(and cause you can drink an alcohol but not an acid: so they are different, aren't they?)  ???

Offline Corribus

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Re: alcohol seems like an acid, but it isn't
« Reply #5 on: April 16, 2013, 11:04:55 AM »
Things aren't categorized as simply as "acid" or "not acid".  Instead there are "degrees of acidity", quantified by pka value.

For instance, phenol is an alcohol that is fairly acidic compared to other alcohols.
What men are poets who can speak of Jupiter if he were like a man, but if he is an immense spinning sphere of methane and ammonia must be silent?  - Richard P. Feynman

Offline sjb

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Re: alcohol seems like an acid, but it isn't
« Reply #6 on: April 16, 2013, 12:14:58 PM »
Why do you feel that the alcohol does not react as an acid?

Because mine is only a theoretical chemistry  ;D

(and cause you can drink an alcohol but not an acid: so they are different, aren't they?)  ???

Of course you can drink an acid - what's vinegar, or lemon juice? Though I'm not suggesting drinking sulfuric, or nitric acids, just to be clear.

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