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Review of Acids
pKa= -logKa
Side note:
Ka= Acid
dissociation
constant.
Acidic Strength
Ka
pKa
Key
= Increase
= Decrease
Acidity of Alcohols
Alcohols are very weak acids and have very large pKa values.
The oxygen in the OH group pulls electron density away from the H atom.
The following charge dispersions result:
This loss of electron density allows H to become labile and ionization can
occur.
Acidity of Alcohols
In the case of the tertiary alcohol, the methyl groups demonstrate the
positive inductive effect.
The polarity of the OH bon in the alcohol is therefore lowered. The oxygen
atom then has a greater tendency to be protonated or rather to stay
protonated. (This contributes to the poor acidity).
Note:
pKa of ethanol= 15.9
pKa of water= 15.73
Note:
The higher the pKa,
the weaker the acid
Acidity of Phenols
Its acidic nature is increased because the electrons on the O in the anion are
unavailable to accept a proton.
Electron-donating groups (for e.g. CH3) pushes the electron density into the ring
which reduces the extent of delocalisation of the lone pair of electrons on the
oxygen atom.
What does this mean?
The attachment group saturates the ring with edensity and the O then reduces the extent to
which it donates its electrons
Note
Note
The carboxylate ion is less
easily protonated than the
phenoxide ion of phenol and
the alkoxide ion of an alcohol
pKa
C2H5COOH
4.88
CH3COOH
4.76
CH2ClCOOH
2.86
CHCl2COOH
1.29
CCl3COOH
0.65
Base Review
Amines are bases because they all contain a nitrogen atom containing a lone
pair of electrons.
This lone pair can easily form a dative bond with an H+ ion in solution.
Basic
Strength
Kb
pKb
Aliphatic Amines
Methylamine pKb=
3.34
Ammonia pKb= 4.74
Aliphatic Amines
alkylammonium ion
Aromatic Amines
Amides
Amino Acids
Amino Acids
Amino Acids
Two functional
groups
Amino Acids
Zwitter:
German for
hybrid
zwitterion
Amino Acids
Amino Acids
Zwitterions as Buffers
Amino Acids
Aspartic Acid