Addallat

7+ Year Member
Jun 2, 2010
126
2
Status
Medical Student
Why is HCl a stronger acid than HClO? Is it because the conjugate base of HClO isn't as great of a nucleophile?


Wouldn't the electron withdrawing effect of the chlorine in hypochlorite make it less reactive therefore the stronger acid?
 
Last edited:
OP
A

Addallat

7+ Year Member
Jun 2, 2010
126
2
Status
Medical Student
I have in my notes "a more stable conjugate base means a stronger acid"

does a more stable conjugate base mean a better nucleophile?
 

texan2414

5+ Year Member
Jul 24, 2013
1,200
733
Status
Medical Student (Accepted)
I don't think so. Species that are stable are less reactive, so their nucleophilicity is probably not as high.
 
OP
A

Addallat

7+ Year Member
Jun 2, 2010
126
2
Status
Medical Student
So why is hypochlorite more reactive than hydrochloric acid? Wouldn't the electron withdrawing effect of the chlorine in hypochlorite make it less reactive therefore the stronger acid?
 
Jul 27, 2014
41
4
Status
Pre-Medical
I feel like the size and difference in electronegativity of HCl makes it a stronger acid.
 

chemtopper

online organic/general chem/MCAT/DAT tutor
10+ Year Member
7+ Year Member
Mar 3, 2009
158
21
Global
www.chemtopper.com
Status
Academic Administration
I feel like the size and difference in electronegativity of HCl makes it a stronger acid.
In HClO --acidic H is bonded to Oxygen :H-O-Cl
However in HCl it is bonded to chlorine
H-Cl
Now if we compare the sizes of chlorine and oxygen - chlorine is bigger is size and hence taking away H+ from chlorine is more easy .The conjugate base Cl- is more stable because it can accommodate negative charge more nicely than OCl- where negative charge is on smaller oxygen atom .I agree that in OCl- electron withdrawing groups are also present but size is the dominating factor and we will decide the acidity of the compound on the basis of the size.
 
  • Like
Reactions: texan2414
Jul 7, 2013
616
161
on your 6
Status
Pre-Medical
I have in my notes "a more stable conjugate base means a stronger acid"

does a more stable conjugate base mean a better nucleophile?
What do you mean by stability? How prone something is to protonation? Disproportionation? Reduction? Oxidation?

I don't think so. Species that are stable are less reactive, so their nucleophilicity is probably not as high.
Br- is a stable species in water solution, at least in the sense that it isn't likely to be protonated. But it's also a great nucleophile in water solution.