September 16, 2024, 03:05:36 PM
Forum Rules: Read This Before Posting


Topic: Why is CH3-CH2-COOH more acidic than CH3-COOH?  (Read 7652 times)

0 Members and 1 Guest are viewing this topic.

Offline polexia

  • Regular Member
  • ***
  • Posts: 9
  • Mole Snacks: +0/-0
Why is CH3-CH2-COOH more acidic than CH3-COOH?
« on: August 14, 2013, 10:38:13 PM »
Alkyl groups are electron donating groups and therefore destabilise the carboxylate group, wouldn't the latter molecule with only one alkyl group be a stronger acid?

Offline magician4

  • Chemist
  • Full Member
  • *
  • Posts: 567
  • Mole Snacks: +70/-11
Re: Why is CH3-CH2-COOH more acidic than CH3-COOH?
« Reply #1 on: August 14, 2013, 10:51:32 PM »
in fact, CH3CH2COOH is the slightly weaker acid ( pKs 4.87) than acetic acid (pKs 4.75), so the whole point of your question is...
... kinda pointless, i would like to say

regards

Ingo
There is a theory which states that if ever anybody discovers exactly what the Universe is for and why it is here, it will instantly disappear and be replaced by something even more bizarre and inexplicable. There is another theory which states that this has already happened.
(Douglas Adams)

Offline Babcock_Hall

  • Chemist
  • Sr. Member
  • *
  • Posts: 5672
  • Mole Snacks: +328/-24
Re: Why is CH3-CH2-COOH more acidic than CH3-COOH?
« Reply #2 on: August 15, 2013, 03:14:34 PM »
The dissociation of a proton from acetic acid to form acetate and a hydronium ion is unfavorable entropically.  IMO explanations about relative acidity of the carboxylic acids should take this effect into account.

Offline antimatter101

  • Full Member
  • ****
  • Posts: 163
  • Mole Snacks: +9/-26
Re: Why is CH3-CH2-COOH more acidic than CH3-COOH?
« Reply #3 on: August 19, 2013, 09:24:30 PM »
Search up something called hyperconjugation. If you are interested, continue to search up 'alkyl shift' and 'hydride shift'. Lastly, search up carbocation. You will find that tertiary carbocations are much less than secondary, primary and methyl cations. Then you should understand why ethanoic acid is weaker than methanoic acid.

Offline MrTeo

  • Chemist
  • Full Member
  • *
  • Posts: 312
  • Mole Snacks: +31/-9
  • Gender: Male
Re: Why is CH3-CH2-COOH more acidic than CH3-COOH?
« Reply #4 on: August 20, 2013, 04:09:45 AM »
You will find that tertiary carbocations are much less than secondary, primary and methyl cations.

Er, no. It's just the opposite.
The way of the superior man may be compared to what takes place in traveling, when to go to a distance we must first traverse the space that is near, and in ascending a height, when we must begin from the lower ground. (Confucius)

Offline antimatter101

  • Full Member
  • ****
  • Posts: 163
  • Mole Snacks: +9/-26
Re: Why is CH3-CH2-COOH more acidic than CH3-COOH?
« Reply #5 on: August 27, 2013, 07:48:49 PM »
Er, sorry. Tertiary carbocation are much more stable than secondary, primary or methyl carbocations. I was sleeping when typing.

Offline trinitrotoluene

  • Regular Member
  • ***
  • Posts: 33
  • Mole Snacks: +3/-0
Re: Why is CH3-CH2-COOH more acidic than CH3-COOH?
« Reply #6 on: August 31, 2013, 11:25:14 PM »
in fact, CH3CH2COOH is the slightly weaker acid ( pKs 4.87) than acetic acid (pKs 4.75), so the whole point of your question is...
... kinda pointless, i would like to say

regards

Ingo

If these pKa's are correct, then the question is invalid.

Offline Borek

  • Mr. pH
  • Administrator
  • Deity Member
  • *
  • Posts: 27785
  • Mole Snacks: +1805/-411
  • Gender: Male
  • I am known to be occasionally wrong.
    • Chembuddy
Re: Why is CH3-CH2-COOH more acidic than CH3-COOH?
« Reply #7 on: September 01, 2013, 03:09:17 AM »
They are correct. pKa for propanoic acid is sometimes given as even slightly higher (but below 5).
ChemBuddy chemical calculators - stoichiometry, pH, concentration, buffer preparation, titrations.info

Sponsored Links