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484

Textbook of Organic Chemistry

18.1.3 Amino Acids


as Zwltterlons

An amino acid has both an acidic

(-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

Amino acid with


free carboxyl group
and free amino aroup

ElectricaUy

neutral

(an internal salt)

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

ACIDS-BASE (AMPHOTERIC) PROPERTIES OF


AMINO ACIDS

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

the amino acids exist in \vater as


Scheme

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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Amino Acids, Peptides and Proteins 485


(iv) Likewise, in a basic solution the amino acid molecule behaves as an acid

NH; group to OH- ions. This converts


negatively charged ion (an anion, Scheme 18.5).

and transfers its proton from the


an amino acid into a

This can migrate to the positively charged electrode (the anode) in an


electrolysis experiment.

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.

In summary, amino acids are neutral a t -one pH. If the

pH is

higher. or

lower than the amino acid has a negative or positive charge.


Problem 18.1: In an electric field. toward which electrode an amino acid will migrate
at (i) a pH

<

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

Zwltterion, thus no migration occurs.

18.3

(a)

From Garboxylic

METHODS OF PREPARATION OF AMINO ACIDS

A carboxylic acid is readily converted to the corresponding cx-bromocarboxylic

Acids-He/I-Vo/hard

acid by the reaction of bromine in the presence of a trace of phosphorous

Zelinsky Reaction

Schemes

9.36

and

9.37).

(see

The treatment of the a-bromo acid with a concen

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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