Alcohol acidity

Lionroar
Posts: 21
Joined: Thu Sep 28, 2017 3:02 pm

Alcohol acidity

Postby Lionroar » Wed Nov 22, 2017 1:26 pm

Hi, this is general question about alcohols. Why are primary alcohols more acidic than secondary and tertiary alcohols? Thank you.
NS_Tutor_Andrew
Site Admin
Posts: 518
Joined: Mon May 23, 2016 1:47 pm

Re: Alcohol acidity

Postby NS_Tutor_Andrew » Tue Nov 28, 2017 6:38 pm

Hi Lionroar,

In general, for questions like this, you always want to look at the stability of the conjugate base, because a highly stable conjugate base = a stronger acid. Alkyl groups are electron-donating, so they will tend to destabilize the negatively charged alkoxide ion. Additionally, steric considerations are relevant -- the alkoxide ion could be stabilized by interactions with the solvent, but this is made more difficult the more bulky substituents there are that get in the way.

Hope this helps!!
Andrew D.
Content Manager, Next Step Test Prep.

Return to “Post your questions here about Next Step's MCAT books”