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3.5 Ranking the Four Factors
It's important to know where all of the protons are.
Chapter 1 covers bond-line drawings if you can't do this.
We need to consider what order of importance to place the four factors in.
The order of importance is what the factors were presented in.
This order has an exception.
A negative charge on nitrogen is more stable than a negative charge on carbon, according to the first factor.
Factor 1 wins over the others.
There are other exceptions, but the one explained above is the most common.
You should be able to apply the four factors and give a qualitative assessment of acidity.
Determine which one is more acidic by comparing the two protons.
The first conjugate base has a negative charge on a nitrogen atom, while the second conjugate base has a negative charge on a carbon atom.
The first conjugate base should be more stable based on this factor alone.
The conjugate bases are not stable by resonance.
The conjugate bases are not stable by induction.
The second conjugate base should be more stable based on this factor alone.
There is a competition between the first factor and the fourth factor.
The first factor takes precedence over the fouth factor.
This is the only exception we saw.
Remember the acronym ARIO if you have trouble remembering the order.
Two protons have been highlighted for each compound.
Determine which of the two protons is more acidic.
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