Quora is the best answer to any question.

Sign up in seconds
SHARE QUESTION

Tweet

Email
Remember Me

Organic Chemistry: What makes methanol (pKa

15.54) a stronger acid than water (pKa 15.74)?

Password

Login

Forgot Password?

SIGN IN TO READ ALL OF QUORA.

Continue with Google

Follow Question

QUESTION TOPICS

Continue with Facebook

Organic Chemistry
Chemistry

2 ANSWERS

ASK TO ANSWER

Richard Liu
8 upvotes byTristan Tan,Sean Ridout,David Pechersky, (more)

The pKa's that you cite are in water, where solvation and H-bonds can make a
large difference so it's hard to gather any information that is of predictive value
from analyzing this alone.
If you take a look at DMSO acidities instead (of course there is still solvation in
DMSO, so this relies on the assumption that it's much less determining a
factor, which is true), it's apparent that methanol is actually quite a bit more
acidic (2.5 pKa units roughly). What's suggested is that the conjugate base of
methanol is stabilized by a hyperconjugative donation of p-type lone pairs on
oxygen into the C-H antibonding orbitals on the methyl. This hyperconjugation
is stronger on methoxide than methanol.
Returning to the problem of solvation, note that changing the solvent to water
increases the acidity of both species by a huge factor. The acidities are closer to
each other because water solvates hydroxide (relative to water) better than it
solvates methoxide (relative to methanol). .
Upvote28 8
Comment
1 byBrian Bi.
Written
Nov,Downvote
2012. Asked
to answer

By continuing you indicate that you have read

and agree to the Terms of Service.

Sign Up with Email

BEST QUESTIONS IN ORGANIC

CHEMISTRY

Phase Transitions: How does water

evaporate below its boiling point?
Do we only consider the penultimate
Carbon atom in the chain to designate
the prefix iso- or neo-?
Why doesn't the drug AZT halt HIV/AIDS
disease course completely?
Why are most alpha helices in proteins
right handed?

Related Questions

Why is pKb rarely used, with basicity usually being reported as the pKa of the
conjugate acid instead?
Why is formic acid a stronger acid than acetic acid?
How does the pKa of Trimethylamine compare with that of ammonia?

Quora User, Biochemistry and Molecular Bio... (more)

3 upvotes by Cynthia Yida, Mark Hamilton, and Ju Fr.

That's a very small difference so the effect can't be large. I would think that the
methyl group might stabilize the negative charge on the oxygen after
deprotonation. Maybe through hyperconjugation, but that seems a little hard
to conceive.
Written 26 May, 2011.
Upvote

Downvote Comment 1

1 Answer Collapsed

Write an answer

Related Questions

Organic Chemistry: Why Methanol is more acidic than water, while ethanol is a
weaker acid than water?
What is it about the structure of bupivacaine that makes it have a higher PKA
than lidocaine?
What is the pKa of DNA?
What is the pKa of amphetamine?

Why does the -amino group of lysine have a higher pKa than the -amino
group?
Organic Chemistry: Why is a low pKa for a base's conjugate acid important for
a ability of a base to become a leaving group?
Why is formic acid stronger than benzoic acid?

Top Stories
Genius and Geniuses: How does it
feel to be a child prodigy, or grow
up as one?
Jessica Su, to be brief
713 upvotes by Quora User, Casey Allen,
Miguel Paraz, (more)

Why am I so scared to ask for

help?
James Altucher, Blogger, author,
social media,... (more)
916 upvotes by Jeremy Johnson, Anonymous,
Diptanshu Purwar, (more)

Growing up as a child prodigy was probably

Kelly La Rue, 1963-1966 Army

Microwave Radio... (more)
369 upvotes by Baldwin Yen (Served in the US
Army reserves, made it to the ... (more) ),
Anonymous, Anonymous, (more)
In the late 60's I was talking to a Sergeant who just
returned from Vietnam and he told me about
enlisted men rolling grenades under their officer's
cots. I was shocked beyond belief. I was upset for

detrimental to me, for the following reasons:

1. I was always in special classes. When I was
five I was already doing algebra, so my
teachers had me sit behind the counter and
work independently while the others were
learning to add. When I was eight my parents
sent me to the eighth grade, where I worked
alongside people twice my height. I saw
nothing...
Read More

Do soldiers ever "frag" or kill their

officers? Why?

several days. This Sergeant went on to tell me he

was on a patrol with a commanding officer who
insisted they follow him into what they, as
experienced soldiers, knew was an ambush. The
office...
Read More

Read More

Sitemap # A B C D E F G H I J K L M N O P Q R S T U V W X Y Z
About - Careers - Privacy - Terms