Why is a primary alcohol more acicic?

[erweightlifter]

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Why is a primary alcohol more acidic considering that alkyl groups donate charge and this usually makes things more acidic?

 

[Gauss44]

Why is a primary alcohol more acidic considering that alkyl groups donate charge and this usually makes things more acidic?

More acidic than what? Primary alcohols aren't very acidic. (methyl<primary<secondary<tertiary)

Why? The more stable the conjugate base, the stronger the acid.

What you mentioned about alkyl groups donating charge is NOT as important as the CARDIO rules. CARDIO rules are a hierarchy of what to consider 1st, 2nd, 3rd... If you consider these factors out of order, by putting the alkyl groups first, you will be wrong sometimes.

 

[mehc012]

More acidic than what? Primary alcohols aren't very acidic. (methyl<primary<secondary<tertiary)

Why? The more stable the conjugate base, the stronger the acid.

What you mentioned about alkyl groups donating charge is NOT as important as the CARDIO rules. CARDIO rules are a hierarchy of what to consider 1st, 2nd, 3rd... If you consider these factors out of order, by putting the alkyl groups first, you will be wrong sometimes.

Whoa, you lost me there. I'm pretty good with chemistry (majored in it), but I've never heard of "CARDIO rules". Sounds like a useful acronym...what is it?

 

[gettheleadout]

Multiquoting because there are a number of things to address here.

Why is a primary alcohol more acidic considering that alkyl groups donate charge and this usually makes things more acidic?

Electron density donation from alkyl groups usually makes things more basic, not acidic, so there's your first problem.

More acidic than what? Primary alcohols aren't very acidic. (methyl<primary<secondary<tertiary)

Why? The more stable the conjugate base, the stronger the acid.

What you mentioned about alkyl groups donating charge is NOT as important as the CARDIO rules. CARDIO rules are a hierarchy of what to consider 1st, 2nd, 3rd... If you consider these factors out of order, by putting the alkyl groups first, you will be wrong sometimes.

I believe OP meant compared to more highly substituted alcohols. Also, electron density donation by alkyl groups is in part due to inductive effects (which fall under DI in the CARDIO acronym), but also due to hyperconjugation, which isn't the acronym, but is only really relevant as a fundamental mechanism of alkyl e- donation.

Whoa, you lost me there. I'm pretty good with chemistry (majored in it), but I've never heard of "CARDIO rules". Sounds like a useful acronym...what is it?

Rules for determining acidity.

C - Charge
A - Atom
R - Resonance
DI - Dipole Induction
O - Orbitals

http://www.masterorganicchemistry.com/2010/09/22/five-key-factors-that-influence-acidity/

 

[mehc012]

Oh, cool. We just never learned an acronym for it.

 

[Helixkam]

electron donating groups will actually lower the acidity of a compound because the higher number of electrons will make the conjugate base less stable.