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(-COOH)
and a basic
(-NH2)
group. The
carboxyl group donates a proton to the amino group and in the solid state,
amino acids exist entirely as the dipolar ions or Zwtterions (Scheme
18.3).
Dipolar ions are electrically neutral since the opposite charges cancel.
R
I
R
I
H- -COOH
H-C-C009
T
:NH2
/1--i
"--'
+NH:r
ElectricaUy
neutral
Amino acid in
zwitterion form
Scheme 18.3
18.1.3 Physical
Properties of Amino
Acids
(i) Since dipolar ions are highly polar, amino acids (inner salts) like salts
melt at fairly high temperatures usually with decomposition.
(ii) These are appreciably soluble in water and in highly polar organic sol
vents, but insoluble in non-polar solvents like petroleum ether, benzene.
(iii) With the exception of glycine, all of the common amino acids are chiral
molecules.
18.2
Amino acids show both acidic and basic properties, i.e. these are amphoteric
substances.
(i) Provided the pH is kept around
neutral dipolar ions (Zwitterions,
6-7,
see
18.2).
(ii) If the pH is made much lower (more acidic) or much higher (more basic),
the form of the amino acid changes.
(iii) If the solution of the amino acid is made acidic. The amino acid behaves
as a base. The coo- group accepts a proton and the amino acid becomes
a positively charged cation (Scheme
18.4).
In an electrolysis experiment,
the amino acid (as a cation) can no\v migrate to a negatively charged
electrode, the cathode.
R
I
R
I
H-C-C009 + tt - H-C-COOH
Net charge
c:)
NH3 +
Neutral (0)
NH3 +
cation
( + 1)
Scheme 18.4
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R
I
H-C-COO 9 + OH9
I
Net charac
c=)
NH3 +
Neutral (0)
R
I
9
... H-C-C00
I
NH2
-1
i
an on
+ H20
( - 1)
Scheme 18.5
(v) The isoelectric point (pl) is the pH at which an amino acid exists only as
a dipolar ion with zero net charge. Thus a pH exists for each amino acid,
its isoelectric point, at which no net migration in an electric field occurs.
pH is
higher. or
<
pl; (ii) pH
>
pl and (Iii) pH
pl?
Answer 18.1: (i) Below the pl, the cationic form predominates, it migrates to the
cathode. (ii) Anionic form predominates at pH's higher than its pl, it migrates to the
anode. (iii) At its pl. the charges are balanced and the amino acid exists as the
18.3
(a)
From Garboxylic
Acids-He/I-Vo/hard
Zelinsky Reaction
Schemes
9.36
and
9.37).
(see
trated solution of aqueous ammonia results in the formation of the amino acid
18.6).
(Scheme
H 0
I II
R-C-C-OH
H
Carboxylic
acid
H
0
H 0
I II
(large cxceu>
I
II
e
R- -c-oH NH, R
--ic-g:
TBr
+NH,
Amino acid
a-Bromocarboxylic
acid
Hell-Volhard-Z.Clinslcy
..
reaction
Scheme 18.6
Problem 18.2: (a) How will you prepare glycine from acetic acid and (b) alanine from
propionic acid?
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