I WISH I HAD A SMALLER pKa
As sung by Ethanol - Based on "I Wish It Could Be Christmas Every Day"
Original Words and Music by Roy Wood
My
name’s C2H6O,
And I’m a weak acid, you know -
I can’t donate H+ to a Bronsted base;
An anion’s stabilised
If charge is delocalised -
Protons leave with ease
And so there is a decrease
In pKa…
And I wish I had a smaller pKa,
‘Cos I can’t quite manage to give my proton away,
Oh I wish I had a smaller pKa -
I wish I was a stronger acid!
Through a pi-bonded framework
Mesomeric effects work -
When double and single bonds alternate there,
So canonical structures
Form when resonance occurs
And where there’s conjugation
There’s delocalisation
Of lone pairs…
So I wish I had a smaller pKa,
‘Cos I can’t quite manage to give my proton away,
Oh I wish I had a smaller pKa,
I wish I was a stronger acid!
(instrumental bit)
My name’s C2H6O (C2H6O)
I’m not as strong as H2O (strong as H2O)
I can’t donate H+ to a Bronsted base;
But when systems can be found (systems can be found)
To move electrons around (electrons around)
Then their Ka is large
Because their negative charge
Is spread (hooray!).
And I wish I had a smaller pKa,
‘Cos I can’t quite manage to give my proton away,
Oh I wish I had a smaller pKa -
I wish I was a stronger acid!
(repeat...)
© Aimee Hartnell, December 2000