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INDIA’S NO. 1 ONLINE COACHING

IIT-JEE ChEmistry by N.J. sir

ORGANIC ChemIstRy

IR
Biomolecules Polymers
&
.S
Practical Organic Chemistry
.J
N

1. IIT-JEE Syllabus

Carbohydrates: Classification – mono, di and polysaccharides (Glucose, Sucrose and Starch only);
hydrolysis of sucrose. Amino acids and Peptides: General structure and physical properties.
Properties and uses of some important polymers (natural rubber, cellulose, nylon, teflon, PVC), Dyes
and their application.

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2. Carbohydrates
2.1 Old Definition

The group of compounds known as carbohydrates received their general name because of early
observations that they often have the formula Cx(H2O)y - that is, they appear to be hydrates of carbon.

Limitations of the old definition: The above definition could not survive long due to the following
reasons:
i) A number of compounds such as rhamnose, (C6H12O5) and deoxyribose (C5H10O4) are known which are
carbohydrates by their chemical behaviour but cannot be represented as hydrates of carbon.

ii) There are other substances like formaldehyde (HCHO, CH2O) and acetic acid [CH3COOH, C2 (H2O)2]
which do not behave like carbohydrates but can be represented by the general formula, Cx(H2O)y.
New definition: Carbohydrates are defined as polyhydroxy aldehydes or polyhydroxy ketones or substances
which give these on hydrolysis and contain at least one chiral carbon atom. It may be noted here that
aldehydic and ketonic groups in carbohydrates are not present as such but usually exist in combination with
one of the hydroxyl group of the molecule in the form of hemiacetals and hemiketals respectively.

IR
2.2 Classification

The carbohydrates are divided into three major classes depending upon whether or not they undergo
hydrolysis, and if they do, on the number of products formed.

i) Monosaccharides: The monosaccharides are polyhydroxy aldehydes or polyhydroxy ketones which

cannot be decomposed by hydrolysis to give simpler carbohydrates. Examples are glucose and fructose,
.S
both of which have molecular formula, C6H12O6.

H
C6H 12O 6 + H 2O  
 No reaction
glucose or
fructose

ii) Oligosaccharides: The oligosaccharides (Greek, oligo, few) are carbohydrates which yield a definite
number (2-9) of monosaccharide molecules on hydrolysis. They include,
.J

a) Disaccharides, which yield two monosaccharide molecules on hydrolysis. Examples are sucrose and
maltose, both of which have molecular formula, C12H22O11.

H
C12H22O11 + H2O 
 C6H12O6 + C6H12O6
sucrose glucose fructose

H
N

C12H22O11 + H2O 
 2C6H12O6
Maltose glucose

b) Trisaccharides, which yield three monosaccharide molecules on hydrolysis. Example is, raffinose,
which has molecular formula, C18H32O16.

H
C18H32O16 + 2H2O 
 C6H12O6 + C6H12O6 + C6H22O6
raffinose glucose fructose galactose

c) Tetrasaccharides, etc.
iii) Polysaccharides: The polysaccahrides are carbohydrates of high molecular weight which yield many
monosaccharide molecules on hydrolysis. Examples are starch and cellulose, both of which have
molecular formula, (C6H10O5)n.

H
(C6H10O5)n + nH2O 
 nC6H12O6
starch glucose

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 In general, the monosaccharides and oligosaccharides are crystalline solids, soluble in water and sweet to
taste. They are collectively known as sugars. The polysaccharides, on the other hand, are amorphous,
insoluble in water and tasteless. They are called non-sugars.

The carbohydrates may also be classified as either reducing or non-reducing sugars. All those
carbohydrates which have the ability to reduce Fehling’s solution and Tollen’s reagent are referred to as
reducing sugars, while others are non-reducing sugars. All monosaccharides and the disaccharides other
than sucrose are reducing sugars.

3. Monosaccharides
The monosaccharides are the basis of carbohydrate chemistry since all carbohydrates are either
monosaccharides or are converted into monosaccharides on hydrolysis. The monosaccharides are
polyhydroxy aldehydes or polyhydroxy ketones. There are, therefore, two main classes of
monosaccharides.
O
||
1. The Aldoses, which contain an aldehyde group (  C  H)

IR
O
||
2. The Ketoses, which contain a ketone group (— C —)

The aldoses and ketoses are further divided into sub-groups on the basis of the number of carbon atoms
in their molecules, as trioses, tetroses, pentoses, hexoses, etc. To classify a monosaccharide completely, it is
necessary to specify both, the type of the carbonyl group and the number of carbon atoms present in the
molecule. Thus monosaccharides are generally referred to as aldotrioses, aldotetroses, aldopentoses,
.S
aldohexoses, ketohexoses, etc.

The aldoses and ketoses may be represented by the H O CH2OH

following general formulas. |
C C=O
| |
(CHOH)n (CHOH)n
.J

| |
CH2OH CH2OH
Aldoses Ketoses
(n = 1, 2, 3, 4, 5) (n = 0, 1, 2, 3, 4)
N

Glucose and fructose are specific examples of an aldose and a ketose.

H O CH2OH
|
C C=O
| |
H – C – OH HO – C – H
| |
HO – C – H H – C – OH
| |
H – C – OH H – C – OH
| |
H – C – OH CH2OH
|
CH2OH fructose
Glucose (an aldohexose) (a ketohexose)

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3.1 Trioses

D and L Terminology: The simplest of all CHO CH2OH

carbohydrates that fit the definition we have given | |
*CHOH C=O
for carbohydrates are the trioses, glyceraldehyde | |
and dihydroxyacetone. Glyceraldehyde is CH2OH CH2OH
aldotriose, and dihydroxyacetone is a ketotriose. Glyceraldehyde Dihydroxyacetone
(an aldotriose) (a ketotriose)

CHO CHO
Glyceraldehyde contains one asymmetric carbon OH H
atom (marked by an asterisk) and can thus exist in
H HO
two optically active forms, called the D-form and
the L-form. Clearly, the two forms are mirror
HO HO
images that cannot be superimposed, that is they D-Glyceraldehyde L-Glyceraldehyde
are enantiomers.
O O

IR
|| ||
1 1
CH D M ea ns on CH
| th e rig ht |
2 2
H – C – OH HO – C – H
| | L M e ans on
3 3 the Left
CH 2 O H CH 2 O H
D-G lyceraldeh yde L -Glycera ldehyd e
.S
The two forms of glyceraldehyde are especially important because the more complex monosaccharides may
be considered to be derived from them. They serve as a reference point for designating and drawing all other
monosaccharides. In carbohydrate chemistry, the Fischer projection formulas are always written with the
aldehyde or ketone groups at the top of the structure. By definition, if the hydroxyl group on the asymmetric
carbon atom farthest from aldehyde or ketone group projects to the right, the compound is a member of the D-
family. If the hydroxyl group on the farthest asymmetric carbon projects to the left, the compound is a member
of the L-family. The maximum number of optical isomers of a sugar is related to the number of asymmetric
carbon atoms in the molecule and may be calculated by the following simple equation.
.J

Maximum Number of Optical Isomers = 2n, where n = the number of asymmetric carbon atoms.
1
Since glyceraldehyde contains only one asymmetric carbon atom, the number of optical isomer is 2 . We
1
know that 2 is = 2, and we have seen that there are indeed two different glyceraldehydes.

3.2 Aldotetroses
N

If we examine the general formula of an aldotetrose, we

1. CHO
see that they contain two asymmetric carbon atoms |
(marked by asterisks). 2. *CHOH
2 |
This means that 2 or 4 optical isomers are possible.
3. *CHOH
They may be represented as the following two pairs: |
an aldotetrose
4. CH2OH

CHO CHO CHO CHO

| | | |
H – C – OH HO – C – H HO – C – H H – C – OH
| | | |
H – C – OH HO – C – H H – C – OH HO – C – H
| | | |
CH2OH CH2OH CH2OH CH2OH
Mirror images (recemic pair) Mirror images (recemic pair)
D (–)-erythrose L (+)-erythrose D (–)-threose L (+)-threose

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 All four isomers have been prepared synthetically. The D- and L-erythrose are mirror images, that is, they are
enantiomers. They have exactly the same degree of rotation but in opposite directions. Equal amounts of the
two would constitute a racemic mixture, that is, a mixture that would allow a plane-polarised light to pass
through the solution unchanged but could be separated into detrorotatory and laevorotatory isomers. The
same comments hold for D- and L-threose. However, D-erythrose and L-threose are not images, that is, they
are diastereomers (optical isomers that are not mirror images are called diastereomers), and the degree of
rotation of each would probably differ.

3.3 Aldopentoses

If we examine the general formula of an aldopentose, we see that they 1. CHO

contain three asymmetric carbon atoms. |
2. *CHOH
|
This means that 23 or 8 optical isomers are possible. These are: 3. *CHOH
- D(–) lyxose, L(+)-lyxose, D(–) xylose, L(–)xylose, D(–) arabinose, L(+)- |
4. *CHOH
arabinose, D(–)-ribose, L(+)-ribose
|
5. CH2OH

IR
an aldopentose

3.4 Aldohexoses

If we examine the general formula of aldohexose, we see that it contains 1. CHO

4
four asymmetric carbon atoms. This means that 2 or 16 optical isomers are |
2. *CHOH
possible. D and L forms of altrose, allose glucose, mannose, galactose,
|
.S
talose, arabinose and idose 3. *CHOH
|
Only three of the sixteen possible aldohexoses are found in nature (all 4. *CHOH
sixteen isomers have been prepared synthetically). They are D-glucose, D- |
mannose, and D-galactose. No one of these three optical iosmers is a mirror 5. *CHOH
image of any of the others, so all three are diastereomers of each other. |
6. CH2OH
an aldohexose
.J

3.5 Epimers

A pair of diastereomers that differ only Epimers Epimers

in the configuration about of a O H O H O H
single carbon atom are said to be C C C
epimers. e.g D(+)- glucose is | | |
H – C – OH H – C – OH HO– C – H
epimeric with D(+) -mannose and
N

| | |
D(+) -galactose as shown below: HO– C – H HO– C – H HO– C – H
| | |
HO– C – H H – C – OH H – C – OH
| | |
H – C – OH H – C – OH H – C – OH
| | |
CH2OH CH2OH CH2OH
D (+)-Galactose D (+)-Glucose D (+)-Mannose

3.6 Cyclic structure of monosaccharides

We know that aldoses (and ketoses) react with alcohols to give first hemiacetals (and hemiketals) and then
acetals (and ketals), i.e.,

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 OH OR
| |
ROH
– C = O + ROH – C – OR  
 – C – OR
–H2O
| | |
H H H
Aldehyde Hemiacetal Acetal

OH OR
| | |
ROH
– C = O + ROH – C – OR  
 – C – OR
–H2O
Ketone Hemiketal ketal

Since monosaccharides contain a number of hydroxyl groups and

an aldehyde or a keto group, therefore, any one of the –OH
groups (usually C4 or C5 in aldohexoses and C5 or C6 in O
ketohexoses) may combine with the aldehyde or the keto group O

IR
furan
to form intramolecular hemiacetal or hemiketal. pyran

As a result, the open chain formulae do not represent the actual structures of the monosaccharides. Their
actual structures are cyclic involving five or six membered rings containing an oxygen atom. The five
membered ring containing one oxygen atom because of its similarity with furan is called the furanose form and
the six membered ring containing one oxygen atom because of its resemblance with pyran is called the
.S
pyranose form. In nut shell, all the monosaccharides (pentoses and hexoses) in the free state always exist in
the pyranose form. However, in the combined state some monosaccharides such as ribose, 2-deoxyribose,
fructose etc., usually exist in the furanose form.

3.7 Cyclic structure of Glucose – Anomers

 
H – 1C – OH H – 1C = O HO –1C – H
.J

| | |
H – 2C – OH H – 2C – OH H – 2C – OH
| | |
HO– 3C – H O HO– 3C – H HO– 3C – H O
| | |
H – 4C – OH H – 4C – OH H – 4C – OH
N

| | |
H – 5C H – 5C – O – H H – 5C
| | |
6 6 6
CH2OH CH2OH CH2OH (II)
(I)
-D(+)-Glucose or D(+)-Glucose -D(+)-Glucose or
-D(+)-Glucopyranose (Open chain form) -D(+)-Glucopyranose

We have discussed above that monosaccharides have cyclic hemiacetal or hemiketal structures. To illustrate,
let us first consider the example of D-glucose. During hemiacetal formation C5 – OH of glucose combines with
the C1 – aldehydic group. As a result, C1 becomes chiral or asymmetric and thus has two possible
arrangements of H and OH groups around it. In other words, D-glucose exists in two stereoisomeric forms,
i.e., -D-glucose and -D-glucose as shown below:

In -D-glucose, the OH group at C1 is towards right while in -D-glucose, the OH group at C1 is towards left.
Such a pair of stereoisomers which differ in configuration only around C1 are called anomers and the C1

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 carbon is called Anomeric carbon (or glycosidic carbon. The cyclic structures of monosaccharides can be
better represented by Haworth Projection formulae. To get such a formula for any monosaccharide (say -and
-D-glucose), draw a hexagon with its oxygen atom at the upper right hand corner. Place all the groups (on
C1, C2, C3 and C4) which are present on left hand side in structures I and II, above the plane of the ring and all
those groups on the right hand side below the plane of the ring.

The terminal – CH2OH group is always placed above the plane of the hexagon ring (in D-series). Following
the above procedure, Haworth Projection Formulae for -D-glucose (I) and -D-glucose (II) are obtained as
shown below:

6 CH2OH 6 CH2OH

5 5
H H H OH

H H
4 1 4 1
OH H  OH H

IR
OH OH OH H
3 2 3 2
I II
H -D-Glucose OH H -D-Glucose
or -D(+)-Glucopyranose
OH
or -D(+)-Glucopyranose

3.8 Cyclic structure of Fructose

.S
Like glucose, fructose also has a cyclic structure. Since fructose contains a keto group, it forms an
intramolecular hemiketal. In the hemiketal formation, C5– OH of the fructose combines with C2-keto group. As
a result, C2 becomes chiral and thus has two possible arrangements of CH2OH and OH group around it. Thus,
D-fructose exists in two stereoisomeric forms, i.e., -D-fructopyranose and -D fructopyranose. However in
the combined state (such as sucrose), fructose exists in furanose form as shown below:

6
2 1 CH2OH O
HO – C – CH2OH OH
.J

| 
3
H – C – OH O 5 2
|
4
H – C – OH H H H CH2OH
| 1
5
H– C
| 4 3
N

6
CH2OH -D-Fructofuranose OH OH

3.9 Mutarotation

The two stereoisomeric forms of glucose, i.e., -D-glucose and -D-glucose exist in separate crystalline forms
and thus have different melting points and specific roations. For example -D-glucose has a m.p. of 419 K
with a specific rotation of +112° while -D-glucose has a m.p. of 424 K and has a specific rotation of +19°.
However, when either of these two forms is dissolved in water and allowed to stand, it gets converted into an
equilibrium mixture of -and -forms through a small amount of the open chain form.

-D-Glucose Open chain form -D-Glucose

(36%) (0.02%) (64%)

As a result of this equilibrium, the specific rotation of a freshly prepared solution of -D-glucose gradually
decreases from of +112° to +52.7° and that of -D-glucose gradually increases from +19° to +52.7°.

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 -D-Glucose Equilibrium mixture -D-Glucose
[ ]D = +112° [] D = +52.7° [] D = +19°
Where [ ] D = specific rotation

This change in specific rotation of an optically active compound in solution with time, to an equilibrium value,
is called mutarotation. During mutarotation, the ring opens and then recloses either in the inverted position or
in the original position giving a mixture of -and--forms. All reducing carbohydrates, i.e., monosaccharides
and disacchardies (maltose, lactose etc.) undergo mutarotation in aqueous solution.

3.10 Reactions of Glucose

a) With HI/P: It undergoes reduction to form n-hexane while with sodium amalgam it forms sorbitol.

HI / P
Glu cos e   CH3  (CH2 )4  CH3
n-hexane

Na / Hg
Glu cos e    CH2OH  (CHOH)4  CH2OH

IR
s-orbitol

b) With H2O: It forms neutral solution

c) With Hydroxylamine (NH2OH)

NH2OH
Glu cos e   HC = NOH
|
.S
(CHOH)4
|
CH2OH
Glucose oxime

d) With HCN: It form addition product cyanohydrin

HCN
Glu cos e  CN
|
(CHOH)5
|
.J

CH2OH
Glucose cyanohydrin

e) Oxidation: Glucose on oxidation with Br2 gives gluconic acid which on further oxidation with HNO3 gives
glucaric acid
Br2 / H2 O HNO 3
Glucose   COOH
N

 COOH Strong


| oxidation |
(CHOH)4 (CHOH)4
| |
CH2OH COOH
Gluconic acid Glucaric acid

f) With Tollen reagent and Fehling solution. Glucose forms silver mirror and red ppt. of Cu2O respectively.
g) With acetic anhydride. In presence of pyridine glucose forms pentaacetate.
5( CH3 CO )2 O
Glu cos e    CHO
C5H5N
|
(CHOCOCH3)4
|
CH2OCOCH3
Glucose pentaacetate

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 h) With phenylhydrazine: it forms glucosazone
C6H5NHNH2
Glu cos e    CH2OH
C5H5N
|
(CHOH)3
|
C = NNHC6H5
|
CH = NNHC6H5
(Glucosazone)

i) With conc. HCl acid: Glucose gives laevulinic acid

Conc . HCl
Glu cos e   CH3 CO  CH2 CH 2  COOH  HCOOH  H2 O
Laevulinic acid

j) Glycoside formation: When a small amount of gaseous HCl is passed into a solution of
D (+) glucose in methanol , a reaction takes place that results in the formation of amomeric methyl acetals.
CH2OH

IR
5 O
H H
CH3OH H
D( ) Glucose   
(Pyranose form) HCl
OH H
HO

H OH OCH3

Methyl -D-glucopyranoside
.S +
Methyl -D-glucopyranoside

Carbolydrate acetals, genrally are called glycosides and an acetal of glucose is called glucoside.

Other reactions
a) Kiliani - Fischer Synthesis: - This is a method of lengthening the carbon chain of an aldose. To illustrate,
we take synthesis of D-threose and D-erythrose (Aldotetroses) from D-glyceraldehyde (an aldotriose).
.J

Addition to HCN to glyceraldehyde produces two epimeric cyanohydrins because reaction creates a new
stereoicenter. The cyanohydrins can be separated easily (since they are diastereomers) and each can be
converted to an aldose through hydrolysis, acidification and lactonisation, and reduction with Na—Hg.
One cyanohydrin ultimately yields D-erythrose and D-threose.
Here we can see that both sugars are D-sugars because starting compound is D-glyceraldehyde and its
N

stereocentrer is unaffected by its synthesis.

b) Ruff Degradation: It is opposite to Kiliani Fischer synthesis that can be used to shorten the chain by a
similar unit. The ruff degradation involves (i) Oxidation of the aldose to an aldonic acid using Bromine
water. (ii)Oxidative decarboxylation of the aldonic acid to the next lower aldose using H2O2 and Fe2(SO4)3.
D-ribose for example can be reduced to D-erythrose.

O
O
O
C——H
C——OH
C——H
H———OH
H———OH
Br
H———OH  2
 H———OH H2O H———OH
2
H2O   + CO2
H———OH Fe2 ( SO 4 )3 H———OH
H———OH
CH2OH
CH2OH CH2OH
D(–) Ribose
D–Ribonic acid
D(–) -Erythrose

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 Exercise 1: Treatment of (+)– glucose with HIO4 gives results that confirm its aldohexose structure.
What product should be formed, and how much HIO4 should be consumed.

4. Disaccharides

Carbohydrates which upon hydrolysis give two molecules of the same or different monosaccharides are called
disaccharides. Their general formula is C12H22O11. The three most important disaccharides are sucrose,
maltose, and lactose. Each one of these on hydrolysis with either an acid or an enzyme gives two molecules
of the same or different monosaccharides as shown below:


H
C12H22O11 + H2O   C6H12O6 + C6H12O6
or Invertase
Sucrose Glucose Fructose


H
C12H22O11 + H2O  
 C6H12O6 + C6H12O6
or Maltase
Maltose Glucose Glucose

H
C12H22O11 + H2O   C6H12O6 + C6H12O6
or Lactase
Lactose Glucose Galactose

IR
Disaccharides may also be considered to be formed by a condensation reaction between two molecules of the
same or different monosaccharides with the eliminatioin of a molecule of water. This reaction involves the
formation of an acetal from a hemiacetal and an alcohol – in which one of the monosaccharides acts as the
hemiacetal while the other acts as the alcohol.

4.1 Sucrose
.S
It is formed by condensation of one molecule of glucose and one molecule of fructose. Unlike maltose and
lactose, it is non-reducing sugar since both glucose (C1 - ) and fructose (C2 - ) are connected to each other
through their reducing centres. Its structure is shown below:

Hydrolysis: (Invert Sugar or Invertose). Hydrolysis of 6

sucrose with hot dilute acid yields CH2OH
.J

D-glucose and D-fructose.

5 O
H H
H
C12H22O11 + H2O 
 C6H12O6 + C6H12O6 H
Sucrose D-glucose D-fructose 4 1
OH H
[ ] D = +66.5° [ ]D = +53° [ ] D = –92°
 -link
Invert Sugar HO 2
N

[ ]D = (+53°) – (–92°) = –39° 3

H OH O  Glycosidic
linkage
Sucrose is dextrorotatory, its specific rotation being (Glucose unit)
+66.5%, D-glucose is also dextrorotatory, []D = +53°, O
CH2OH  -link
but D-fructose has a large negative rotation, []D = -92°.
Since D-fructose has a greater specific rotation than D-
glucose, the resulting mixture is laevorotatory.
Because of this the hydrolysis of sucrose is known as H H OH CH2OH
the inversion of sucrose, and the equimolecular mixture
of glucose and fructose is known is invert sugar or
invertose.
OH H
(Fructose unit) Sucrose

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5. Polysaccharides

Polysaccharides are formed when a large number (hundreds to even thousands) of monosaccharide
molecules join together with the elimination of water molecule. Thus, polysaccharides may be regarded as
condensation polymers in which the monosaccharides are joined together by glycosidic linkages. Some
important polysaccharides are:

1. Cellulose 2. Starch 3. Glycogen

4. Gums and 5. Pectins

5.1 Starch

It is a polymer of glucose. Its molecular formula is (C6H10O5)n where the value of

n (200 – 1000) varies from source to source. It is the chief food reserve material or storage polysaccharide of
plants and is found mainly in seeds, roots, tubers, etc. Wheat, rice, potatoes, corn, bananas etc., are rich
sources of starch.

Starch is not a single compound but is a mixture of two components – a water soluble component called

IR
amylose (20%) and a water insoluble component called amylopectin (80%). Both amylose and amylopectin
are polymers of -D-glucose.

Amylose is a linear polymer of -D-glucose. It contains about 200 glucose units which are linked to one
another through -linkage involving C1 of one glucose unit with C4 of the other as shown below:
C1 – C4 – -linkage
.S
(– Glucose – Glucose – Glucose – Glucose –)n
Linear Polymer

Amylopectin, on the other hand, is a highly branched polymer. It consists of a large number (several
branches) of short chains each containing 20-25 glucose units which are joined together through -linkages
involving C1 of one glucose unit with C4 of the other. The C1 of terminal glucose unit in each chain is further
linked to C6 of the other glucose unit in the next chain through C1 – C6 -linkage. This gives amylopectin a
.J

highly branched structure as shown below.-

C1  C4 -linkage
Glucose  Glucose  Glucose
 C1  C6 -linkage
N

Glucose  Glucose  Glucose

 C1  C6 -linkage
Glucose  Glucose  Glucose

Hydrolysis: Hydrolysis of starch with hot dilute acids or by enzymes gives dextrins of varying complexity,
maltose and finally D-glucose. Starch does not reduce Tollen’s reagent and Fehling’s solution.
Uses: It is used as a food. It is encountered daily in the form of potatoes, bread, cakes, rice etc. It is used in
coating and sizing paper to improve the writing qualities. Starch is used to treat textile fibres before they are
woven into cloth so that they can be woven without breaking. It is used in manufacture of dextrins, glucose
and ethyl alcohol. Starch is also used in manufacture of starch nitrate, which is used as an explosive.

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6. Amino Acids

6.1 Introduction and Nomenclature

Amino acids are molecules, which contain two functional groups, one is carboxylic group and another is amino
group. Amino acids are derivatives of carboxylic acids in which one hydrogen atom of carbon chain is
substituted by Amino group.

Amino group may be at , ,  position with respect to carboxylic group

H2N  CH2  COOH Amino acetic acid, or Glycine

CH3  CH (NH2)  COOH  - Amino propionic acid or Alanine
H2N  CH2  CH2 COOH  - Amino propionic acid
H2N  CH2  (CH2)2  COOH  - Amino butyric acid

Some amino acids contain a second carboxyl group or a potential carboxyl group in the form of carboxamide:

IR
these are called acidic amino acid some contain a second basic group which may be an amino group these
are called basic amino acids.

HOOC  CH2  CH  COOH H2N  CH2  CH2  CH2  CH2  CH  COOH

 
NH2 NH2
Aspartic acid Lysine
.S
(Acidic amino acid) (Basic amino acid)

6.2 Physical Properties and Structure

Although the amino acids are commonly shown as containing an amino group and a carboxyl group, certain
properties are not consistent with this structure.

1. In contrast to amines and carboxylic acids, the amino acids are nonvolatile solids, which melt at fairly high
temperatures.
.J

2. They are insoluble in organic solvents [i.e. non polar solvents] and are highly soluble in water.

3. Their aqueous solution is neutral.

4. Their aqueous solutions behave like solutions of substances of high dipole moment.
N

5. Acidity and basicity constants are ridiculously low for - COOH and – NH2 groups

All these properties are quite consistent with a dipolar ion structure for the amino
acids (I)
+
H3N  CHR  COO––
(I)
Amino acid : dipolar ions

In the physical properties melting points, solubility, and high dipole moment are just what would be expected
of such a salt.

The acid base properties also become understandable when it is realized that the measured Ka actually refers
+
to the acidity of an ammonium ion, RNH3

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 +
H3NCHRCOO– + H2O H3O+ + H2NCHRCOO–

[H3O  ][H2NCHRCOO  ]
Ka 
[  H3N  CH  RCOO  ]

–
and Kb actually refers to the basicity of a carboxylate ion, RCOO

+
H3N  CH  RCOO– + H2O +
H3N  CHR COOH + OH–

[  H3N  CHR  COOH][OH ]

Kb 
[  H3NCHRCOO ]

When the solution of an amino acid is made alkaline, the dipolar ion(I) is converted to the anion (II); the
stronger base, hydroxide ion, removes a proton from the ammonium ion and displaces the weaker base, the
amine

+
H3N  CHRCOO– + OH– H2N CHRCOO– + H2O

IR
(I) (II)
Stronger Stronger Weaker Weaker
acid base base acid

When the solution of an amino acid is made acidic; the dipolar ion I is converted into the cation (III); the
stronger acid H3O , gives up a proton to the carboxylate ion, and displaces the weaker carboxylic acid.
.S +
H3N CHRCOO + H3O
– + +
H3N CHRCOOH + H2O
(I) (III)
Stronger Stronger Weaker Weaker
base acid acid base

In summary, the acidic group of a simple amino acid like glycine is  NH3 not –COOH, and basic group is –
-
COO not –NH2.
.J

Exercise 2: The amino acids in water acts as ampholyte. Explain?

6.3 Iso Electric Point

What happens when a solution of an amino acid is placed in an electric field depends upon the acidity or
basicity of solution. In quite alkaline solution.
+
N

+
H H
H2N-CHRCOO– +
– [Link]
– +
– H3 [Link]
OH OH
(II) (I) (III)

Anions (II) exceed cations (III), and there is a net migration of amino acid toward the anode. In quite acidic
solution cations (III) are in excess, and there is a net migration of amino acid towards the cathode. If (II) and
(III) are exactly balanced, there is no net migration; under such conditions any one molecule exists as a
positive ion and as a negative ion for exactly the same amount of time and any small movement in the
direction of one electrode is subsequently cancelled by an equal movement back towards the other electrode.
The hydrogen ion concentration of the solution in which a particular amino acid does not migrate under the
influence of an electric field is called the isoelectric point of that amino acid.

An amino acid shows its lowest solubility in a solution at the isoelectric point, since here there is the highest
concentration of the dipolar ion. As the solution is made more alkaline or more acidic, the concentration of one
of the more soluble ions, II or III increases.

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 If an amino acid has amino group and one carboxyl group, it has two pK values. The isoelectric point (PI) of
this amino acid has the average value of the both pK values.
We take example of glycine.
+ + – +
H3 N  CH2  COOH H3N  CH2  COO + H …(1)
Conjugated acid (CA) Dipolar Ion (DI)

[DI][H ]
At equilibrium K1 
[CA ]
+ – – +
H3N  CH2  COO H2N  CH2  COO + H …(2)
DI Conjugated Base (CB)

[CB][H ]
At equilibrium K 2 
[DI]

[DI][H  ] K 2 [DI]
[CA] = [CB] =
K1 [H  ]

IR
At isoelectric point [CA] = [CB]

[DI][[Hi ] K 2 [DI] +
 
Where [Hi ] = conc. of [H ] at isoelectric point.
K1 [Hi ]

or, [Hi ] 2 = K1 K2
+
.S
or, 2log [Hi ] = log K1 + log K2
+
or –2 log (Hi ] = - log k1 – logK2
or 2pHi = pK1 + pK2
pK 1  pK 2
or pHi =
2
7. Peptides
.J

As the amino acid molecules contain both basic as well as acidic group it might be expected that an
intermolecular reaction may take place between the carboxyl group of one amino acid and the amino group of
another amino acid, with the elimination of a molecule of water.

R R R R
N

   
H2N  CH  COOH + H2N  CH  COOH  H2 N  CHCO  NH  CHCOOH
Since the resulting molecule still has a free amino and a carboxyl group, it may react with other amino acids at
either of the ends to give a higher molecular weight linear or condensation product. Every two amino acids are
linked by means of a –CO-NH group, which is commonly referred as peptide bond. So now we can define a
peptides as the amides formed by interaction between amino groups and carboxyl groups of amino
acids.
Depending upon the number of amino acid residues per molecule, they are known as dipeptides, tripeptides
and so on and finally polypeptides.
7.1 Naming of Polypeptide
A convenient way of representing peptide structures by use of standard abbreviations. According to
convention the N-terminal amino acid residue [having the free amino group] is written as the left and the C
terminal amino acid residue (having the free carboxyl group) at the right end.

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 A peptide is named by indicating its sequence of amino acids beginning with the N-terminal residue.
H2N  CH  CONH  CH  CONH  CH  CONH  CH  CONHCH2 COOH
| | | |
CH3 CH2-OH CH2-C6H5 CH2-CONH2
Alanine Serine Phenylalamine Asparagine glycine
This pentapeptide is called alanyl-sery-phenylalanyl-asparaginyl-glycine or using the common abbreviations
as H-Ala-Ser-phe-Asn-gly-OH. All naturally occurring important peptides, however, posses a shorter individual
name.

7.2 Structure of Poly peptides

To identify the structure of a peptide, the peptide in question is first hydrolysed to its constituent amino acids,
which are separated and identified. The amount of each amino acid is measured, and hence the number of
each kind of amino acid can be calculated.
The next problem is to determine the sequence of the various amino acids constituting the peptide. This is
very difficult task, because there is a large number of possibilities in which the constituent amino acids may be
linked in the peptide, e.g. even is a dipeptide, having glycine and alanine, the two amino-acids may be present
in either of the two ways.

IR
CH3 CH3
 
H2N – CH2 – CO – NH – CH – COOH H2N – CH – CO – NH – CH2 – COOH
Glycylalanine Alanylaglycine

The two structures differ in the respect that in the first the N-terminal amino acid is glycine (i.e. the amino
.S
group of glycine is free) and C-terminal amino acid is alanine, while in the latter the N-terminal amino acid is
alanine and C-terminal acid is glycine. Various chemical methods have been developed to remove either of
the two terminal amino acid residues of a polypeptide in a stepwise manner and hence the arrangement of the
various amino acids in a polypeptide can be established.
7.3 Sanger’s Method
Sanger reagent, 1-fluoro-2, 4-dinitrobenzene (FDNB) was first used to determine that which amino acid
constituted the amino end of the polypeptide. The method consists in treating the polypeptide with the reagent
.J

in the presence of sodium-hydrogen-carbonate solution at room temperature to form a 2, 4-dinitrophenyl

(DNP) derivative of the polypeptide. The product is hydrolysed be means of acid (which causes the cleavage
of the peptide bond connecting the N-terminal amino acid to the rest of the polypeptide molecule) to form
dinitrophenyl (DNP) derivative of the N-terminal amino acid and the rest of the polypeptide molecule or amino
acid residues.
N

O2N   F + H2N  CH  CO  NH  CH  CO  NH  CH  COOH

  
 R1 R2 R3
NO2

HF + O2N   NH  CH  CONH  CH  CONH  CH  COOH

  
 R2
R1 R3
NO 2
H+

O2N   NH  CH  CONH + H2N  CH  COOH + H2N  CH  COOH

  

R1 R2 R3
NO2
2, 4 – DNP derivative Aminoacid mixture

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 8. Dyes

8.1 Definition

The chemical substances which are used to impart colour to fabrics, foods and other objects for their
beautification and distinction are called dyes.

These chemical substances used as dyes are capable of getting fixed to the fabrics permanently and are
resistant to the action of water, soap, light, acid and alkalies.

The colour of dyes is attributed to their ability to absorb some wavelengths of visible region of electromagnetic
spectrum (380 nm to 760 nm). The part of the colour which reflected back gives the colour of the dye i.e.
complementary to the colour absorbed. The colour of visible light absorbed and the complementary colour
reflected are listed in table.
Wave length (nm) Colour absorbed Complementary colour
400 – 435 Violet Yellow, Green
435 – 480 Blue Yellow

IR
480 – 490 Greenish Blue Orange
490 – 500 Bluish Green Red
500 – 560 Green Purple
560 – 580 Yellowish Green Violet
580 – 595 Yellow Blue
.S
595 – 605 Orange Greenish Blue
605 – 750 Red Blue, Green

In the earlier days fabrics were coloured by the dyes mainly from Alizarin (red dye) and indigo (blue dye). But
now a days, many natural dyes have been synthesized in the laboratory. This helped us to produce dyes of
desired shades which otherwise are not available in natural dyes.
.J

8.2 Classification

These dyes have been classified into two categories

a) Classification based on constitution: Depending upon the characteristic structural units the dyes are
classified as follows.
N

Sl. No. Type of Dye Structural Unit Examples

O

N Martius yellow,
1. Nitro dyes
O Naphthol yellow
(Nitro group)
–N=N– Orange-I, Orange-II,
2. Azo dyes
(azo group) Congo red
Malachite green,
3. Triphenyl methane dyes (C6H5)3C –
Rosaniline

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 O

O Phenolphthalein,
4. Phthalein dyes
C
Mercurochrome

O
(Phthalein group)
O
C

5. Anthraquinone dyes C
Alizarin
O
(anthraquinone group)
O

C
6. Indigoid dyes Indigo, Tyrian purple

IR
C

O
Indigoid group

Structures

OH
.S NO2
+
SO3Na N
N OH
NO2
(Martius yellow)
(Orange-I)

HO
.J

OH
O
OH

C
OH
O
O
N

C
(Alizarine)
O
(Phenolphthalein)

O H
+
C N N (CH 3)2
C C

N C C

H O
(Indigo)

N(CH3 )2
(Malachite green)

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 Diphenyl methane dye
+
N N (CH3)2
(H3C)2

NH2 Auromine – 0

8.3 Classification Based on Application

A particular dye may be suitable for one kind of fibre and may be unsuitable for the other. For example, a dye
suitable for wool and silk may not be applied or used for dyeing cotton or rayon. Thus based on the class,
shade and other properties like resistance to acids, alkalies, and fastness to light a classification of dyes is
done, as given below:

a) Acid dyes b) Basic dyes

IR
c) Direct dyes d) Disperse dyes
e) Fibre reactive dyes f) Vat dyes
g) Insoluble azodyes h) Mordant dyes

a) Acid dyes: These dyes are characterised by the presence of acid group like sulphonic acid (– SO3H),
carboxylic acid (– COOH) and phenolic group. The presence of such groups make the dyes more soluble
.S
and also serve as the reactive points for fixing the dye to the fibre.

Application: These dyes are applied to wool, silk and nylon. These have no affinity for cotton.

Examples: Orange-I and Orange-II can be obtained by the action of sulphonic compounds with naphthols
or by coupling sulphonic compounds with naphthols.
.J

HO

+ - + -
Na O 3 S N N Cl +
N

-naphthol

HO

N
- +
SO 3 Na N

Orange-I

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 HO

- + + -
SO3 Na N N Cl +

-naphthol

HO
- +
SO3 Na N
N

IR
Orange-II

b) Basic Dyes: These dyes contain (–NH2) group or (–NR2) group as chromophore (colour bearing group) or
auxochrome (colour enhancing group). In acidic solutions these form water soluble cations. These dyes
use the anionic side on the fabric to get themselves attached.

Application: This type of dyes is used to dye nylon, polyester, wool, cotton, leather, paper, etc.
.S
Example

N
1. Aniline yellow
N NH2
.J

N CH3
2. Butter yellow
N N
CH3
N

N
3. Crysodine G N NH2

NH2

c) Direct Dyes: These dyes also belong to the class of azo dyes and are used to dye the fabrics directly by
placing it in aqueous solution of the dye. The direct dyes attack the fibre by means of hydrogen bonding.

Application: These are very effective for dying cotton, wool and rayon

Example:

1. Martius yellow

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 2. Congo Red

NH2

N H2 N
N N
HO N

- +
SO 3 Na

c) Disperse Dyes: These dyes, as the name signifies, are usually applied in the form of a dispersion of
finely divided dye in a soap solution in the presence of phenol, cresol or benzoic acid.

IR
Application: These are mainly used to dye rayon, dacron nylon, synthetic fibres, polysters and poly
acrylonitrile.

Examples:
O
NH2
.S
1. Celliton fast pink B

O
HO
O
NH CH3
.J

2. Cellition fast blue B

O
HN
N

CH3

d) Fibre Reactive Dyes: These dyes are used to dye fibres like cotton, wool or silk. These are linked to the
fibre by virtue of the hydroxy or amino group present on the fibre. These dyes induce fast colour on fibres
which is retained for a longer time.

e) Insoluble azo dyes: The dyes belonging to this class are directly synthesised on the fibre. The fabric to
be coloured is soaked in an alkaline solution of phenol or naphthol and is than treated with a solution of
diazotised amine to produced the azo dye on the surface of the fabric.

Application: These dyes can be used to dye cotton silk, polyester, nylon, etc.

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 Example:
O 2N

N
N

HO
(Nitroaniline red)

f) Vat Dyes: Before being introduced on to fabric these dyes are first reduced to colourless leuco
compounds in wooden vats by alkaline reducing agent. The fibre is then soaked in the solution of the dye.
After proper absorption of the dye, the fibre is then exposed to air or to an oxidising agent. By doing so the
dye gets oxidised to yield insoluble coloured dye on the fabric.

Example: Indigo dye

g) Mordant Dyes: A dye which imparts different colours to the fabric in the presence of different metal ions
(called mordants) is referred to as mordant dye. Nowadays it is rarely used
Application: These dyes are used for dyeing of wool. The method involves the precipitation of certain
substances on the fabrics which then combine with the dye with the dye to form an insoluble coloured

IR
complex called lake. Depending on the kind of mordant used different colours. For example, Alizarin, a
mordant dye, gives red colour with aluminium and tin salts, where as brownish red colour chromium
mordant and black violet with iron mordant.

9. Polymers

9.1 Introduction
.S
Sit quietly and think about your activities today from the morning. You wake up in the morning, You want to
brush your teeth. You fetch your toothpaste. The tube is made up of a polymer. Your brush is made up of a
polymer. When you want to rinse your mouth, you open your plastic(polymer) tap. The pipe lines used to bring
water to your tap is made of PVC(polymer). Skip it. You start preparing your break fast. You take a non-stick
tawa. Non-stick? What does that mean? What is it made of? It is poly tetrafluoro ethylene abbreviated as
teflon, a polymer. See, how polymers play an important role in our daily life from dawn to dusk. The molded
chair in which you are sitting is a polymer. The pen with which I'm writing this is a polymer. Want to know
more about polymers? Read further.
.J

Polymers can be called as macromolecules. Macromolecules can be considered as an association of small

molecules to give a big molecule. Macromolecules can be man-made, too. The first syntheses were aimed at
making substitutes for the natural macromolecules, rubber and silk; but a vast technology has grown up that
now produces hundreds of substances that have no natural counterparts. Synthetic macromolecular
compounds include: elastomers, which have the particular kind of elasticity characteristic of rubber; fibers,
long, thin and threadlike, with the great strength along the fiber that characterizes cotton, wool, and silk; and
N

plastics, which can be extruded as sheets or pipes, painted on surfaces, or molded to form countless objects.
We wear these manmade materials, eat and drink from them, sleep between them, sit and stand on them;
turn knobs, pull switches, and grasp handles made of them; with their help we hear sounds and see sights
remote from us in time and space; we live in houses and move about in vehicles that are increasingly made of
them.

9.2 Polymers and polymerization

Macromolecules, both natural and man-made, owe their great size to the fact that they are polymers (Greek:
many parts); that is, each one is made up of a great many simpler units — identical to each other or at least
chemically similar — joined together in a regular way. They are formed by a process we touched on earlier:
polymerization, the joining together of many small molecules to form very large molecules. The simple
compounds from which polymers are made are called monomers.

Polymers are formed in two general ways.

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 a) In chain-reaction polymerization, there is a series of reactions each of which consumes a reactive
particle and produces another, similar particle; each individual reaction thus depends upon the previous
one. The reactive particles can be free radicals, cations, or anions. A typical example is the polymerization
of ethylene. Here the chain-carrying particles are free radicals, each of which adds to a monomer
molecule to form a new, bigger free radical.

CH  CH
Rad. + CH2 = CH2  RadCH2CH2  
2

2
 RadCH2CH2CH2CH2  etc.

b) In step reaction polymerization, there is a series of reactions each of which is essentially independent
of the preceding one; a polymer is formed simply because the monomer happens to undergo reaction at
more than one functional group. A diol, for example, reacts with a dicarboxylic acid to form an ester; but
each moiety of the simple ester still contains a group that can react to generate another ester linkage and
hence a larger molecule, which itself can react further, and so on.
H 2 CH 2 COH

O OH

HOCH 2 CH 2 OH + HOOC COOH C C

1,2-Ethanediol
O O
terephthalic acid
O

IR
OH
HOCH 2 CH 2 OH
    O

O
HO
p-C 5 H 4 (COOH) 2
O
HOOC
O

O
O
.S O O
OH

a) Free-radical vinyl polymerization: In we discussed briefly the polymerization of ethylene and substituted
ethylenes under conditions where free radicals are generated — typically in the presence of small
amounts of an initiator, such as a peroxide. Reaction occurs.

initiator
nCH2 = CH     – CH2CHCH 2CHCH2CHCH2CH –
.J

| | | | |
G G G G G

Vinyl monomer or (– CH 2CH –)n

|
N

G
Polymer

At the doubly bonded carbons — the vinyl groups — and is called vinyl polymerization. A wide variety of
unsaturated monomers may be used, to yield polymers with different pendant groups (G) attached to the
polymer backbone. For example.

CH2 = CH  – CH2 – CH – CH2 – CH – CH2 – CH –

| | | |
Cl Cl Cl Cl
Vinyl chloride Poly (vinyl chloride)
(PVC)

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 CH2 = CH  CH2 – CH – CH2 – CH – CH2 – CH – CH2 – CH –
| | | | |
CN CN CN CN CN
Acrylonitrile Polyacrylonitrile
(Orlon)

CH2 = CH  CH2 – CH – CH2 – CH – CH2 – CH –

| | | |
C6H5 C6H5 C6H5 C6H5
Styrene Polystyrene

b) Copolymerization: So far, we have discussed only polymerisation of a single monomeric compound to

form a homopolymer, a polymer made up — except, of course, at the two ends of the long molecule — of
identical units.

Now, if a mixture of two (or more) monomers is allowed to undergo polymerization, there is obtained a
copolymer a polymer that contains two (or more) kinds of monomeric units in the same molecule. For

IR
example:
CH 3 CH3
| |
initiator
CH2 = CH + CH2 = C      – CH 2 – CH – CH2 – C –
| | | |
Ph COOCH 3 Ph COOCH3
Styrene Methyl methacrylate Polystyrene (co-methyl methacrylate)
.S
Through copolymerization there can be made materials with different properties than those of either
homopolymer, and thus another dimension is added to the technology. Consider, for example, styrene.
Polymerized alone, it gives a good electric insulator that is molded into parts for radios, television sets, and
automobiles. Copolymerization with butadiene (30%) adds toughness; with acrylonitrile (20-30%) increases
resistance to impact and to hydrocarbon; with maleic anhyride yeilds a material that, on hydrolysis, is water-
soluble, and is used as a dispersant and sizing agent. The copolymer in which butadiene predominates (75%)
butadiene, 25% styrene) is an elastomer, and since World War II has been the principal rubber substitute
.J

manufactured in the United States.

Copolymers can be made not just from two different monomers but from three, four, or even more. They can
be made not only by free-radical chain reactions, but by any of the polymerization methods we shall take up;
ionic, coordination, or step-reaction. The monomer units may be distributed in various ways, depending on the
technique used. As we have seen, they may alternate along a chain, either randomly or with varying degrees
N

of regularity. In block copolymers sections made up of one monomer alternate with sections of another:

— M1M1M1M1M1 – M2M2M2M2 — Block copolymer

If graft copolymers, a branch of one kind is grafted to a chain of another kind:

— M1M1M1M1M1M1M1 —
|
M2M2M2M2

Fibres are long thin, threadlike bits of material that are characterized by great tensile (pulling) strength in the
direction of the fiber. The natural fibres – cotton, wool, silk – are typical. Fibres are twisted into threads, which
can then be woven into cloth, or embedded in plastic material to impart strength. The tensile strength can be
enormous, some synthetic fibres rivaling – on a weight basis – steel.

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 The gross characteristics of fibres are reflected on the molecular level – the molecules, too, are long, thin, and
threadlike. Furthermore, and most essential, they lie stretched out alongside each other, lined up in the
direction of the fiber. The strength of the fiber resides, ultimately, in the strength of the chemical bonds of the
polymer chains. The lining-up is brought about by drawing – stretching — the return to random looping and
coiling is overcome by strong intermolecular attractions. In a fiber, enthalpy wins out over entropy. This high
degree of molecular orientation is usually — although not always — accompanied by appreciable crystallinity.

An elastomer possesses the high degree of elasticity that is characteristic of rubber: it can be greatly
deformed — stretched to eight times its original length, for example — and yet return to its original shape.
Here, as in fibres, the molecules are long and thin; as in fibres, they become lined up when the material is
stretched. The big difference is this: when the stretching force is removed, the molecular chains of an
elastomer do not remain extended and aligned but return to their original random conformations favored by
entropy. They do not remain aligned because the intermolecular forces necessary to hold them that way are
weaker than in a fiber. In general, elastomers do not contain highly polar groups or sites for hydrogen
bonding; the extended chains do not fit together well enough for Vander Waals forces to do the job. In an
elastomer entropy beats enthalpy.

IR
H O H
| || |
N C N
C N C
|| | ||
O H O
.S H O H
| || |
N C N
C N C
|| | ||
O H O
H O H
| | |
.J

N C N
C N C
|| | ||
O H O

Hydrogen bonding in crystallites of nylon-6,6

N

One further requirement the long chains of an elastomer must be connected to each other by occasional cross
– links: enough of them to prevent slipping of molecules past one another; not so many as to deprive the
chains of the flexibility that is need for ready extension and return to randomness.

Natural rubber illustrates these structural requirements of an elastomer; long flexible chains; weak
intermoecular forces and occasional cross – linking. Rubber is cis 1,4-polyisoprene . With no highly polar
substituents, intermolecular attraction is largely limited to van der Waals forces. But these are weak because
of the all – cis configuration about the double bond. Figure below compares the extended chains of rubber
with those of its trans stereoisomer. As we can see, the trans configuration permits highly regular zig – zags
that fit together well; the cis configuration does not. The all-trans stereoisomer occurs naturally as gutta
percha; it is highly crystalline and non-elastic.

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 (a)

(b)

Extended chains of (a) natural rubber, cis-1,4 –polyisoprene, and of (b) gutta
percha, its trans stereoiosmer.

Chief among the synthetic elastomers is SBR, a copolymer of butadiene (75%) and styrene (25%) produced
under free-radical conditions; it competes with natural rubber in the main use of elastomers, the making of
automobile tires. All-cis polybutadiene and polyisoprene can be made by Ziegler – Natta polymerization.

An elastomer that is entirely or mostly polydiene is, of course, highly unsaturated. All that is required of an
elastomer, however, is enough unsaturation to permit cross-linking. In making butyl rubber for example, only
5% of isoprene is copolymerized with isobutylene.

IR
Exercise 3: What is the difference between addition and condensation polymersiation give an
examples.

Some Important Polymers:

a) Natural Rubber: Natural rubber is an addition polymer of isoprene (2-methyl-1,3-butadiene)

.S
Rubber has an average chain length of 5000 monomer units of isoprene.

The rubber in which the arrangement of carbon chain is trans with respect to the double bond is known as
Gutta Percha and this is the natural rubber obtained from bark of various trees. Natural rubber is sticky
material. This disadvantage is removed by 'VULCANISATION' which involves addition of sulphur to rubber
and heating the mixture. sulphur forms short chains of sulphur atoms that link two hydrocarbon (isoprene)
units together.
.J

CH 3 CH 3

----CH—C=CH—CH 2—CH—C=CH—CH 2----

S
S

----CH—C=CH—CH 2—CH 2—C=CH—CH—CH------

N

CH 3 CH3

When tension is applied the chains can strengthen out but they cannot slip past each other because of
sulphur bridges. Thus rubber can be stretched only to a certain extent and hydrocarbon chains have the
tendency to regain their shape when tension is removed. Vulcanised rubber is thus stronger and less
sticky than the natural rubber.

b) Synthetic rubber: (Polychloroprene) or Neoprene) It is obtained by free radical polymerisation of

chloroprene in

Cl Cl

nCH2=C—CH=CH 2  (–CH 2—C=CH—CH 2—)n

Neoprene

it is a thermoplastic and need not to be vulcanised. It is a good general purpose rubber and superior to
natural rubber as it is resistant to the reaction of aire, heat, light chemicals, alkalis and acids below 50%

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 strength. It is used for making transmission belts, printing rolls and flexible tubing employed for
conveyence of oil and petrol.

c) Buna rubbers: Butadiene polymerises in the presence of sodium to give a rubber substitute viz. BuNa. It is
of two types

i) Buna - N or GRA: it is synthetic rubber obtained by copolymerisation of one part of acryl nitrile and
two parts of butadiene.

nCH 2=CH—CH=CH 2 + nCH 2=CH  —CH 2—CH=CH—CH 2 —CH 2—CH

CN BUNA-S CN n

It is more rigid responds less to heat and very resistant to swelling action of petorol, oils and other
organic solvents.

ii) Buna -S or GRS (General purpose Styrene rubber): It is a copolymer of three moles of butadiene and
one mole of styrene\ and is an elastomer. It is obtained as a result of free radical copolymerisation of

IR
its monomers.

nC6 H5CH=CH2 + nCH 2=CH—CH=CH 2 [–CH 2–CH=CH–CH 2–CH–CH 2–]n

C 6H 5
BUNA-S

It is generally compounded with carbon black and vulcanised with sulphur. It is extremely resistant to
.S
wear and tear and finds use in manufacture of tyres and other mechanical rubber goods.

d) Teflon: It is polymer of tetrafluorethylene (F2C=CF2) which on polymerisation gives Telfon.

(NH )2 S 2O8 870 1020K

nCF2=CF2  4      (—CF2—CF2—)n

It is thermoplastic polymer with a high softening point (600K). It is very tough and difficult to work. It is
inert to most chemicals except fluorine and molten alkali metals. It withstands high temperatures. Its
.J

electrical properties make it an ideal insulating material for high frequency installation.

e) Nylon -66: It is a polymer resin. It is a condensation polymer formed by reaction between adipic acid and
hexamethylene diamine. Both monomer units consist of 6 carbon atoms and therefore named nylon -66.

O H
N

|| |
H2O
HO  C  (CH2 )4  C OH  H  N (CH2 )6  NH2  

 O O H 
 || || | 
  C (CH2 )4  C N (CH2 )6  NH    
 
 
Nylon  66
( A condensation copolymer)

It is thermoplastic polymer when extruded above its melting point (536 K) through spinneret, it gives nylon
fiber which is extremely tough and resistant to friction. It possess greater tensile strength, elasticity and
lusture than any natural fiber. It is chemically inert and is fabricated into sheet, bristles and textile fibres.

f) Nylon 6 or Perolon - L: A polyamide is prepared by prolonged heating of caprolactam at 530 - 540 K.

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 NH  
  
(CH 2)5       ( CH 2 ) 5 C
540 K
||
 NH  ( CH ) 5 C  NH  
||
C=O  O O 
Nylon  6

The fiber is practically identical to Nylon in properties

Exercise 4: Complete the reactions

O O
CH2 OH
+ nHO C C OH
nHO CH2

-2nH2O

Exercise 5: a) What is the structure of nylon-6, made by alkaline polymerisation of caprolactom?

O
C

IR
N
H
Caprolactam

b) Suggest a mechanism for the process. Is polymerisation of the chain reaction or

step reaction type?
.S
8. Solutions to Exercise

Exercise 1: Since in glucose there are five –OH groups so five moles of HIO4 are consumed giving
main product formic acid and formaldehyde as shown below :

Glucose + 5HIO4  5HCOOH + HCHO

Exercise 4: O O
.J

O C C~

D= CH 2 CH2

O
N

H H
| |
Exercise 5: a) ~~ N(CH2 )5 C  N(CH2 )5 C ~~
|| ||
O O

b)
–
Base – C (CH2)5 – NH
Base: C–N O
O H

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 Base – C (CH2)5 – NH
– H
–
O Base – C (CH2)5 – N – C(CH2)5 – NH , etc
C–N O O
O H

The reaction is anionic chain reaction polymerization, involving nucleophilic substitution at

–
the acyl group of the cyclic amide. The base could be OH itself or the anion formed by
abstraction of the –NH proton from a molecule of lactam.

9. Solved Problems (Subjective)

9.1 Subjective

Complete the reactions (Question 1 to 3)

A
Problem 1: nCF2 = CF2  (–CF2 – CF2 –)n Teflon
heat , high pressure

IR
Solution: A = (NH4)2S2O8

Problem 2: nCH2 CH K 2 S2 O8
C CH2   B

Cl

Solution:
.S  
B =   CH2  C  CH  CH2  
 | 
 Cl n
neprene

Problem 3: nHO – CH2 – CH2 – OH + C

-2nH2O

O O
.J

– O – CH2 – CH2 – O – C C–
Terelene

O O
Solution:
C= C C
N

nHO OH
Terephathalic acid

Problem 3: Give the classification of polymers obtained from esters of acrylic acid (CH2 =
[Link])
Formula of
Solution: Polymer Characteristics Uses
monomer
Hard transparent, Lenses,
CH3 CH3 high optical transparent
H2 C C
clarity. It is object
( H3C C )n
capable of domes and
COOC2H 5 COOCH3
methylacrylate Polymethylacrylate
acquiring skylights
different colours plastic
and tints jewellery

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 H2C C ( H2 C CH )n
Tough and Similar to
COOC2H5
COOC 2 H5 rubbery polymer above
ethyl acrylate Polyethylacrylate

Used in
OH 2 CH
preparing
( H2 C C )n Hard, horney and
cloth,
CN
CN
high melting
acrylonitrile carpets
Polyacrylonitrile material
and
blankets

Problem 4: a) Show how an aldohexose can be used to synthesize 2-ketohexose. (b) Since
glucose is converted to fructose by this method, what can you say about the
3 4 5
configurations of C , C and C in the sugars.

CHO CH = NNHC6H5
2C6H5CHO
(CHOH)4 + 3C6H5NHNH2  C = NNHC6H5

IR
–C6H5NH2 –2C6H5CH = NNHC6H5
– H2O
CH2OH – NH3
(CHOH)3
Aldohexose
CH2OH
Osazone

H–C=O CH2OH
.S
C=O C=O
Zn/CH3COOH
(CHOH)3 (CHOH)3
CH2OH CH2OH
Osone 2-ketohexose

Here aldohexose reacts with one molecule of phenylhyrazine which condenses with
.J

the aldehyde group to give phenylhydrazone. When warmed with excess of phenyl
hydrazine, the secondary alcoholic group adjacent to the aldehyde group is oxidised
by another molecule of phenylhydrazine, to a ketonic group. With this ketonic group,
the third molecule of phenylhydrazine condenses to give osazone. The
phenylhydrazinyl group is transferred from osazone to C6H5CHO giving C6H5CH =
NNHC6H5 and a dicarbonyl compound called an osone. The more reactive aldehyde
N

group of the osone is reduced, not the less reactive keto group and it gives the 2-
ketohexose.

b) The configurations of these carbons which are unchanged in the reactions, must be
identical in order to get the same osazone.

Problem 5: a) Supply structures for H through K. Given:

NH 2 OH / base Ac O / NaOAc  HOAC NaOMe / MeOH

An aldohexose     H  2   I   J     K.

b) Explain the last step (c). What is net structural change (d) Name this overall
method. (e) Discuss the possibility of epimer formation.

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 Solution: a) H is an oxime HOCH2(CHOH)4CH = NOH; I is the completely acetylated oxime,
AcOCH2(CHOAc)4CH = NOAc that loses 1 mole of HOAc to form J,
AcOCH2(CHOAc)4 CN; K is an aldopentose, HOCH2(CHOH)3CHO.

b) The acetates undergo transesterification to give methyl acetate freeing all the sugar
OH’s. This is followed by reversal of HCN addition.

c) There is loss of one C from the carbon chain.

d) Wohl degradation

e) The -CHOH becomes the –CH = O without any configurational changes of the other
chiral carbons. Thus no epimers are formed.

Problem 6: Although both polymers are prepared by free radical processes, poly (vinyl
chloride) is amorphous and poly (vinylidene chloride) (saran) is highly crystallilne.
How do you account for the different? (vinylidene chloride is 1,1-dichloroethene).

IR
H H H H H Cl H Cl
| | | | | | | |
Solution: ~~ C  C  C  C ~~ ~~ C  C  C  C ~~
| | | | | | | |
H Cl H Cl H Cl H Cl
Poly ( vinyl chloride ) PVC Poly ( vinylidene chloride ) saran

As poly (vinyl chloride) is able to show stereoisomerism and further it is formed by a free
radical process, it is atactic (chlorine atoms distributed randomly), the molecules fit
.S
together poorly.
Poly (vinylidene chlroide) has two identical substituents on each carbon and the chains fit
together well.

Problem 7: Show the fundamental unit of structure common to all polypeptides and proteins
and show how cross linking occurs between two chains by H - bonding.

Solution: O H R
.J

N
N
R O H

R H O
N
N

N N
O R
H

Problem 8: How will you synthesize Alanine from acetylene.

Solution: CN
H 2O HCN
CH CH   CH 3CHO   
 CH 3—CH
H 2SO 4 ,HgSO 4 NH 3 NH 2
+
H3 O
COOH
CH 3—CH
NH 2
Alanine

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 + –
Problem 9: Glycine exists as (H3N CH2COO ) while anthranilic acid
(P–NH2–C6H4 – COOH) does not exist as dipolar ion.

Solution: –COOH is too weakly acidic to transfer H+ to the weakly basic –NH2 attached to the
electron withdrawing benzene ring. When attached to an aliphatic carbon, the –NH2 is
sufficiently basic to accept H+ form
–COOH group.
Problem 10: i) Sulphanilic acid although has acidic as well as basic group, it is soluble in
alkali but insoluble in mineral acid
ii) Sulphanilic acid is not soluble in organic solvents.
Solution: i) Sulphanilic acid exist as Zwitterion

– +
HO3S   NH2  O3S   NH3

The weakly acidic –+NH3 transfers H+ to OH– to form a soluble salt, P–NH2–C6H4–
SO 3 Na+ on the other hand – SO 3 is too weakly basic to accept H+ from strong

IR
acids.
ii) Due to its ionic character it is insoluble in organic solvents.
Problem 11: Why should isoelectric point for Aspartic acid (2.98) be so much lower than that of
leucine?
Solution: This may be explained by considering following ion equilibria
+
– H
.S
OOCCHCH 2COOH HOOCCH—CH 2COO
–H
+ HOOC—CH—CH 2 COOH

+NH + +
3 NH 3 NH 3
(A) (B) (C)
+ +
+H –
– –
OOC—CH—CH 2COO

NH 3
+
(D)
.J

It is apparent that ions (A) and (B) are neutral, while (C) is a cation and (D) is dianion. In
species (D), the anion is derived from the second —COOH group present in aspartic acid
and is not possible in leucine. At neutral pH a significant concentration of (D), will be
present in aqueous solution. It will therefore, be necessary to decrease the pH of such a
solution if the formation of (D) is to be suppressed to a stage where anions and cations
are present in equal concentration (the isoelectric point).
N

9.2 Objective
Problem 1: Nylon-66 is a polyamide of
(A) Vinylchloride and formaldehyde
(B) Adipic acid and methyl amine
(C) Adipic acid and hexamethylene diamine
(D) Formaldehyde and melamine

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 Solution: O O

+ H2N NH2
HO (CH2)4 OH (CH2)6

O O H

C (CH2)4 C N (CH2) 6 NH
Nylong-66
 (C)

Problem 2: Which of the following is not a condensation polymer?

(A) Glyptal (B) Nylon-66
(C) Dacron (D) PTFE

Solution: Others are condensed polymer

 (C)

IR
Problem 3: Which of the following is an example of basic dye?
(A) Alizarine (B) Indigo
(C) Malachite (D) Orange – I

Solution: +
N (CH 3)2
.S
C
.J

N(CH3 )2
 (C)
Problem 4: Which of the following is not a chromophone?
(A) – NH2 (B) – NO
(C) – NO2 (D) – N = N –
N

Solution: Chromophore is colour bearing group

 (A)

Problem 5: Which of the following is a natural fibre?

(A) Starch (B) Cellulose
(C) Rubber (D) Nylon-6

Solution: (B)
EXERCISE – I

Q.1 Which of the following statement is not correct for maltose.

(A) It is a disaccharide
(B) It undergoes mutarotation
(C) It is a reducing sugar
(D) It does not have hemiacetal group

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Q.2 Identify the correct statement about lactose.
(A) It consists of one galactose and one glucose unit
(B) Mutarotation is not possible
(C) Anomeric carbon of galactose is attached to 4 carbon of glucose which is -1,
4-glycoside bond.
(D) Lactose is used to cleave the -1, 4-glycoside bond

Q.3 Which of the following carbohydrates would be most abundant in the diet of strict vegetarian?
(A) Amylose (B) Glycogen (C) Cellulose (D) Maltose

Q.4 Which of the following statements about the structure of glycogen is true.
(A) Glycogen is a copolymer of glucose and galactose
(B) There are more branch residues than residues in straight chains.
(C) The monosaccharide residue alternate between D and L-glucose
(D) New glucose molecules are added to the C-2 aldehyde group of chain termini forming a hemiacetal.

IR
Q.5 D-Ribose when treated with dilute HNO3 forms

HO O HO O

H OH H OH
(A) H
.SOH, Achiral (B) HO H , Chiral
H OH H OH

HO O O OH

HO O HO O
.J

H OH H OH
(C) HO H , Achiral (D) H OH, Chiral
H OH H OH

HO O O OH
N

Q.6 Consider the given process.

CHO CHOH CHO

H –C –OH C –OH HO –C –H
– –
HO H OH HO H OH HO H
H2O H2O
H OH H OH H OH
H OH H OH H OH

CH2OH CH2OH CH2OH

(I) (II) (III)

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 and identify the incorrect statement.
(A) Configuration at C-2 is lost on enolisation
(B) I and III are epimers
(C) Proton transfer from water to C-1 converts ene diol to an aldose
(D) D-glucose can isomerise to D-fructose through enol intermediate.

Q.7 Consider the given structure and select the incorrect statement:
HOCH2
O HOCH2 O CH2OH

HO H HO
HO OMe H OMe

OH H

CH2OH
HOCH2 HO H
O

IR
O H
HO
H
HO OH
OMe H OH OMe

H OH
(A) (I) Hydrolyse much faster than (III)
.S
(B) (III) Hydrolyse much faster than (I)
(C) (II) Hydrolyse much faster than (IV) in acidic medium
(D) Compound (IV) is methyl--D-glucofuranoside

Q.8 Select the incorrect statement:

(A) Starch is a homopolymer of glucose forming an -glycosidic chain
(B) Maltose and Lactose are disaccharides
.J

(C) Cellulose has only -D-glucose unit which are joined by glycosidic linkage between C1 of one glucose unit
and C4 of another glucose unit
(D) The structure of glycogen is similar to amylose
Q.9 When methyl D-glucopyranaside is treated with HIO4 its number of mole consumed per mole of the sugar is :
(A) 2 (B) 3 (C) 4 (D) 5
N

Q.10 - amino acid when heated with BaO forms.

(A) ,-unsaturated acid(B) , -unsaturated amine
(C) Carboxylic acid (D) Amine

Q.11 The configuration of the C-2 epimer of D-glucose is:

(A) 2R, 3S, 4R, 5S (B) 2S, 3S, 4R, 5R
(C) 2S, 3R, 4S, 5R (D) 2R, 3S, 4R, 5R

Q.12 Mutaratation involve:

(A) Racemisation
(B) Diastereomerisation
(C)Optical resolution
(D) Conformational inversion

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Q.13 Consider the reaction sequence-
PhNHNH
2 H O Zn
Glucose     P 3 
 Q 
 R
excess  AcOH
The product R is-
(A) Arbinose (B) Sorbitol (C) Fructose (D) Mannose

COO–

Q.14 The pH of the solution containing following zwitter ion species is NH3 H

R
(A) 4 (B) 5 (C) 7 (D) 9

Q.15 Peptide linkage is:

IR
O O O O

(A) – C – O – (B) – C – NH2 (C) – C – NH – (D) – C – NH –NH2

–
Q.16 Same osazone derivative is obtained in case of D-glucose, D-Mannose and D-Fructose due to:
(A) the same configuration at C-5
(B) the same constitution
.S
(C) the same constitution at C-1 and C-2
(D) The same constitution and acid configuration at C-3, C-4, C-5 and C-6 but different constitution and
configuration at C-1 and C-2 which becomes identical by osazone formation
4 NaBH
Q.17 D(–) –Erythrose    (P)
4 NaBH
D(–) – Threose    (R)
Which of the following statement is correct about P and R?
.J

(A) Both are optically active

(B) Both are optically inactive
(C) P is optically inactive and R is optically active
(D) Neither P nor R has asymmetric carbon
Q.18 The monomer of nucleic acids are held together by
N

(A) Phosphoester linkage (B) Amide linkage

(C) Glycosidic linkage (D) Ester linkage
Q.19 Select the incorrect statement:
(A) Manufacture of paints require glyptal (B) Water pipes are made up of PVC
C6H5

(C) Bakelite has free carbonyl group (D) Polystyrene is (CH2 – CH)n
Q.20 Select incorrect statement about Nylon 2- nylon-6.
(A) It is a copolymer
(B) It is biodegradable
(C) It is an alternating polyamide
(D) It is made up of CH3 –CH –COOH and H2N(CH2)5COOH.

NH2

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Mob. No. : 9214233360
Q.21 Which of the following cannot be used as drying agent for a liquid organic compound
(A) Anhydrous CaCl 2 (B) Anhydrous K2CO3
(C) Metallic sodium in the form of wires (D) Anhydrous H2SO4

Q.22 The ferrox reagent used for detection of oxygen present in a given compound contains:
(A) K4[Fe(CNS)6] (B) K3[Fe(NCS)6]
(C) Fe[Fe(CNS)6] (D) Fe[Fe(NCS)6]

Q.23 When N and S both present the Lassaignes test is sometimes incomplete due to formation of
(A) Na(CNS) (B) Na(NCS)
(C) NaCN (D) Na2S

Q.24 The polymer formed as a result of following sequence of reaction is:

1. HCl
CuCl 2. Cu2Cl2

IR
2HC  CH HC  CH –CH = CH2 CH2 = C –CH = CH2
NH4Cl
Cl
polymerisation

[ CH2 – C = CH = CH2]

Cl
(A) Saran
.S (B) PVC (C) Neoprene (D) Chloroprene

Q.25 Consider the reaction-

OH

(i) CHCl  NaOH

  3   P(major) + Q(minor)
(ii) H3O
.J

Mixture of A and B can be best separated by-

(A) Steam distillation (B) Vacuum distillation
(C) Fractional distillation (D) Crystallisation

Q.26 Select the incorrect statement-

N

(A) The Lassaigne's filtrate must be clear and colourless solution

(B) Presence of colour in Lassaigne's filtrate indicates incomplete fusion
(C) The Lassaigne's filtrate solution is alkaline
(D) The Lassaigne's filtrate solution must be neutral

Q.27 When Na-extract is added to small amount of freshly prepared FeSO4 solution and small amount of NaOH a
green coloured precipitated is obtained. This indicates.
(A) Presence of SN (B) Presence of Fe(OH)2]
(C) Presence of Fe(CN)2 (D) Presence of Na4[Fe(CN)6]

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Plot No. 68, Near Union Bank of India, Rajeev Gandhi Nagar, Kota, Rajasthan – 324005
Mob. No. : 9214233360
Q.28 Consider the following sequence
NaOH [Link] /
Na (extract) + FeSO4  
 (A)   Green colour
H2SO 4

Freshly Solution
n
prepared sol . (Filtrate)
The presence of green colour confirm the presence of
(A) N (B) S
(C) O (D) N and S both

Q.29 When solidum extract is treated with FeCl 3 solution a blood red coloured is obtained due to the presence of :

(A) SO3H (B) NH2 SO3H

(C) H2N COOH (D) H2N

IR
Q.30 The monomer that undergo radical polymerization most easily is
(A) CH2 = CH2 (B) C6H5CH = CH2
Me
(C) CH2 = C (D) CH3 – CH = CH2
Me
.S
Q.31 The monomer that can undergo radical, cationic and anionic polymerization with equal case :
(A) Me –C = CH2 (B) Ph–CH = CH2

Me
(C) CH2 = CH2 (D) CH2 = CH –CN

Q.32 Select the incorrect statement about polymer

.J

(A) Polymers do not carry any charge

(B) Polymers have high viscosity
(C) Polymers scattered light
(D) Polymers have multiple bond

EXERCISE – II
N

Q.1 Carbohydrates may be:

(A) Sugars (B) Starch
(C) Polyhydroxy aldehyde/ketones (D) Compounds that can be hydrolysed to sugar

Q.2 Select the correct statement:

(A) S-glyceraldehyde is also known as L-glyceraldehyde
(B) The configuration of the stereocenter most distant from the carbonyl group determines whether a
monosaccharide is D or L.
(C) Glucose and all naturally occurring sugars are D-sugars
(D) D-erythrose and D-threose are diastereomers

Q.3 Select the incorrect statement.

(A) Monosaccharide are insoluble in organic solvents like diethyl ether.
(B) Anomers of a cyclic monosaccharides differ in the position of the OH group at the hemiacetal carbon.
(C) D-ribose the OH group used to form the five membered furanose ring is located on C4
(D) Aldopentoses and ketohexoses form pyranose rings in solution.

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Mob. No. : 9214233360
Q.4 Select the correct statement.
(A) Glycosides do not undergo mutarotation
(B) All OH groups of a cyclic monosaccharides are converted to ethers by treatment with base and an alkyl
halide
(C) - D glucose reacts with Ag2O and excess CH3I to form tetramethyl ether
(D) D-glucose upon treatment with warm HNO3 forms D-glucaric acid

Q.5 All disaccharides may have

(A) One acetal (B) Two acetal
(C) One acetal and One hemiacetal (D) Two hemiacetal

Q.6 Starch molecules are polymer with repeating glucose units. Select the correct statement(s).
(A) Glucose units are joined through -glycosidic linkage
(B) The branches of amylopectin are linked to the chain with -1,6-glycosidic linkages
(C) The linear linkages of amylopectin are formed by -1,6-glycosidic bond
(D) Amylose has an unbranched skeleton of glucose molecules with -1, 4-glycosidic linkages.

Q.7 Select the correct statement:

(A) Proteins upon hydrolysis gives -amio acid only

IR
(B) Except glycine, all other naturally occurring -amino acids are optically active.
(C) In fibrous proteins polypeptide chains are held together by hydrogen and disulphide bonds
(D) Keratine is insoluble in water

Q.8 Select the correct statement:

(A) Coiling of polypeptide chain form fibrous protein
(B) Quarternary structure of protein also exist
(C) Lysine is an amino acid with basic side chain
.S
+ –
(D) The absolute configuration of H3N –CH(CH2OH)COO (L-serine) is S.

Q.9 Select the correct statement:

(A) All proteins are polyamides formed by joining amino acids together.
(B) All L-amino acids except cysteine have the S-configuration.
(C) All amino acids are 1° amines except praline.
(D) Proline is a 2° amine consisting of five membered ring.
.J

Q.10 Select the correct option:

(A) Isoelectric point is the pH at which an amino acid exists primarily in its neutral form.
+
(B) Isoelectric point is the average of pKa values of -COOH amino -NH3 groups [valid only for neutral
amino acid].
(C) Glycine is characterised by two pKa values.
(D) For neutral amino acid the concentration of zwitter ion is maximum at its isoelectric point.
N

Q.11 Amino acids are synthesised from:

(A) -Halo acids by reaction with NH3.
(B) Aldehydes by reaction with NH3 and cyanide ion followed by hydrolysis.
(C) Alkyl halides by reaction with the enolate anion derived from diethyl acetamidomalonate and hydrolysis.
–
(D) Alcohols by reaction with NH3 and CN ion followed by hydrolysis.

Q.12 Which of the following carbohydrates developes blue colour on treatment with iodine solution?
(A) Glucose (B) Amylose (C) Starch (D) Fructose

Q.13 Select the correct statement:

(A) High density polythene is a linear polymer.
(B) Low density polythene is a branched chain polymer.
(C) Chain growth polymers are also known as addition polymer.
(D) Step growth polymer is also known condensation polymer.

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Mob. No. : 9214233360
Q.14 Select the correct statement:
(A) Chain growth polymerisation takes place through radical, cation or anion intermediate.
(B) A synthetic polymer is polydisperse
1
(C) M n is given by
N i
 MiNi , where Ni in the number of molecules with molar mass Mi and there are N
molecules.
(D) Weight average molar mass is inversely proportional to the mean square molar mass

Q.15 Select the correct statement:

(A) Elastomers have the weakest intermolecular forces
(B) Buna-N is an elastomer with crosslinks
(C) Some fibres have crystalline nature
(D) Thermoplastic polymers have stronger intermolecular forces than fibres

Q.16 Consider the given sequence of reaction

Na(extract) +Dil. HNO3  Filtrate (A) + (B)
Violet
Cool

IR
AgNO3
Clear solution (C)
NH4OH
(white)
Select the correct statement:
– –
(A) Na extract contains Br and I together
(B) B is vapour of I2
(C) The clear solution contains AgCl
+
(D) The clear solution contains [Ag(NH3)2]
.S
CHO
AcONa
Q.17 + AC2O   (P)

Before isolating (P) unreacted Ph–CHO is removed first. Select the correct statement:
(A) P is cinnamaldehyde
(B) Removal of PhCHO is done by passing steam into the mixture
.J

(C) Removal is done by simple distillation

(D) P is cinnamic acid

Q.18 Match the column:

Column-I Column-II
(A) Sucrose (P) Two acetals
(B) Maltose (Q) No hemiacetal
N

(C) Lactose (R) -1,4-glycosidic bond

(D) Cellulose (S) Hydrolysis product is glucose

Q.19 Match the column:

Column-I Column-II
(A) (CH2 – C = CH – CH2)n (P) Thermoplastic polymer
Cl
H H O O
(B) (N –(CH2)6 – N – C –(CH2)4 –C)n (Q) Thermosetting polymers

Cl

(C) (CH2 –CH)n (R) Fibres

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Mob. No. : 9214233360
 OH OH

(D) (S) Elastomer

Q.20 Match the column:

Column-I Column-II
(Component of mixture) (Reagent)
(A) Crystalline Na2CO3 + Sodium citrate + (P) Fehling solution
CuSO4(aq. sol.)
(B) CuSO4 + Rochelle Salt + NaOH (Aq. sol.) (Q) Nesseler's Reagent
(C) 10% -naphthol in alcohol (R) Bennedict's solution
(D) HgCl + KI + KOH (aq. sol.) (S) Molisch's Reagent

IR
EXERCISE – III

Assertion Reason:

Q.1 Statement I : Furanose ring. like pyranose rings are not planar.
Statement II : The most stable conformation of furanose is envelope form.
.S
(A) Statement- I is true, statement- II is true and statement- II is correct explanation for
statement- I
(B) Statement- I is true, statement- II is true and statement- II is NOT correct explanation for
statement- I
(C) Statement- I is true, statement- II is false.
(D) Statement- I is false, statement- II is true.

Q.2 Statement I : Bromine water changes glucose to gluconic acid

Statement II : Bromine water acts as oxidising agent
(A) Statement- I is true, statement- II is true and statement- II is correct explanation for
.J

statement- I
(B) Statement- I is true, statement- II is true and statement- II is NOT correct explanation for
statement- I
(C) Statement- I is true, statement- II is false.
(D) Statement- I is false, statement- II is true.

Q.3 Statement I : All monosaccharide ketoses are reducing sugars.

N

Statement II : Monosaccharide ketose give positive Tollen's and Fehling's test

(A) Statement- I is true, statement- II is true and statement- II is correct explanation for
statement- I
(B) Statement- I is true, statement- II is true and statement- II is NOT correct explanation for
statement- I
(C) Statement- I is true, statement- II is false.
(D) Statement- I is false, statement- II is true.

Q.4 Statement I : Amylose chain adopts a helical arrangement

Statement II : Presence of -1,4-glycosidic bonds force to adopt a helical shape.
(A) Statement- I is true, statement- II is true and statement- II is correct explanation for
statement- I
(B) Statement- I is true, statement- II is true and statement- II is NOT correct explanation for
statement- I
(C) Statement- I is true, statement- II is false.
(D) Statement- I is false, statement- II is true.

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Mob. No. : 9214233360
Q.5 Statement I : PHBV is a biodegradable polymer.
Statement II : PHBV undergoes bacterial degradation in the environment.
(A) Statement- I is true, statement- II is true and statement- II is correct explanation for
statement- I
(B) Statement- I is true, statement- II is true and statement- II is NOT correct explanation for
statement- I
(C) Statement- I is true, statement- II is false.
(D) Statement- I is false, statement- II is true.

Comprehension (6 to 8)

Consider the following reversible process for a reaction of D-glucose.

+
H
Y
-D isomer
CH2OH O
+ CH3OH
H

IR
HO [X]
HO
OH OH Z
H+ -D isomer
D-glucose
( or  form)

Q.6 The structure of intermediate [X] is:


CH2OH O
CH2OH O
.S
(A) HO (B)
OH
HO OH O OH

CH2OH O CH2OH O

(C) HO (D) HO
OH
O
.J

HO HO OH

Q.7 Select the correct option:

CH2OH O CH2OH O

(A) Y is HO H (B) Z is HO OCH3

N

HO OH HO OH
OMe H

CH2OH O CH2OH O

(C) Y is OH (D) Z is HO H
H OH HO OH
OCH3 OCH3

Q.8 Select the correct statement.

(A) Y is more stable than Z due to H-bond
(B) Y is less stable than Z due to anomeric effect
(C) Y is more stable than Z due to anomeric effect
(D) Y is less stable than Z due to H-bond

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Comprehension (9 to 11)
Consider the given data for a given sample of.
–1
Molar mass Interval/Kg mol Average molar mass within Mass of sample within
Internal/Kg mol–1 Interval/g
5-10 7.5 9.60
10-15 12.5 8.70
15-20 17.5 8.75
20-25 22.5 5.6
–1
Q.9 The number average molar mass in kg mol is:
(A) 10.25 (B) 11.91 (C) 12.87 (D) 13.65

Q.10 The weight average molar mass in kg mol –1 is:

(A) 8.76 (B) 10.36 (C) 12.06 (D) 14.16

Q.11 The polydispersity index of the polymer is:

(A) 0.29 (B) 0.84 (C) 1.18 (D) 2.1

Comprehension ([Link].12 to Q. 14)

IR
G
The monomer (G = Me or Cl) when treated with Zieglar-Natta catalyst undergo polymerisation

in the manner given below-

Zieglar-Natta
n
.S
Catalyst
n
cis-poly-1,3-butadiene
Q.12 The Zieglar-Natta catalyst is:
(A) TiCl4 (B) R3Al (C) R3Al/TiCl 4 (D) R3B/TiCl4

Cl
.J

Q.13 The polymer obtained when monomeric unit used is CH2 = C –CH = CH2
(A) Neoprene (B) Stilbene (C) Styrene (D) Chlopropicrin

Q.14 Which of the following statement is not true considering the process given above:
(A) The general class of polymer formed is known as homopolymer
(B) The polymer obtained is stereoregular
(C) Buna-N can be prepared using above process
N

(D) Synthetic rubber can be formed by above process using 1,3-butadiene.

Q.15 Match the column

Column-I Column-II
(A) - anomer of a D-monosaccharide (P) CH2OH at C-5 and OH at C-1 are cis to
each other
(B) - anomer of a D-monosaccharide (Q) OH at C-1 and CH2OH at C-5 are trans
to each other
(C) Haworth projection of - anomer (R) OH group is drawn down at C-1
(D) Haworth projection of -D-anomer (S) Major isomer at equilibrium

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Mob. No. : 9214233360
Q.16 Match the compounds given below existing in equilibrium mixture with their percentage given in the right hand
side.
Column-I Column-II
H O
C

H OH
(A) (P) 6%
H OH
H OH

CH2OH
O

HO OH
(B) (Q) 18%
OH

OH

IR
HOH2C O H

(C) H H OH (R) < 1%

H

OH OH

HOH2C O OH

(D) H H (S) 56%

H H
.S
OH OH

Q.17 Match the column:

Column-I Column-II
(Carbohydrate) (Properties)
(A) Starch (P) Mutarotation
(B) Sucrose (Q) Non reducing sugar
(C) Lactose (R) -glycosidic bond
.J

(D) Maltose (S) -glycosidic bond

(T) Reducing sugar
(U) Hemiacetal

Q.18 Match the column:

Column-I Column-II
CH2OH O
N

H
HO CH2OH O
HO OH OH
(A) O (P) -glycoside bonds
HO OH
H

HOCH2 O OH
H H
OH OH
HO OH O
(B) O (Q) Reducing sugar
OH
HOCH2

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Mob. No. : 9214233360
 O
CH2OH
H
HO
HO HO
HOCH2
O O
(C) HO
(R) Forms enediol intermediate
CH2OH

OH
HOCH2 HOCH2
O O

(D) HO O OH (S) -glycoside bond

HO OH HO OH

Q.19 Match the column:

Column-I Column-II
(Functional group) (Test used or complex during confirmatory test)

IR
–3
(A) Aldehydic (P) [(C6H5O)6Fe] (Violet)
–
CH– C – O

O O
(blue)
(B) Phenolic (Q) Cu
O O
.S
CH –––– C – O–

RCH(OH) OSONH
(C) Alcohol (R)
C NH

RCH(OH) OSONH
violet red
(S) (ROH)2 Ce(NO3)4 (Red)
(T) Molisch's Test
.J

Q.20 Match the column:

Column-I Column-II
(A) Addition polymer (P) Buna-S
(B) Condensation polymer (Q) Buna-N
(C) Homopolymer (R) Polythene
(D) Copolymers (S) Nylon 6,6
N

Q.21 Match the column :

Monomer Catalyst Polymer
(A) CH2 = CH2 (1) Peroxide (P) Teflon
(B) CF2 = CF2 (2) Persulphate & high P (Q) LDP
(C) CH2= CHCN (3) Ziegler-Natta Catalyst (R) HDP
P=6, 7 atm (S) Polyacrylonitrite

Q.22 Match the column :

Presence of the element in Complex formed in one Colour of the complex
Na-extract of the test
(A) N (P) Na4[Fe(CN)5NOS] (W) Prussian Blue
(B) S (Q) Fe(CNS)3 (X) Black
(C) N and S together (R) PbS (Y) Violet
(S) Fe4[Fe(CN)6] (Z) Blood Red

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Mob. No. : 9214233360
Subjective

Q.23 Identify A to D

Br2 N H
+ Na/Hg
Aldose A B C D
H2O CO2

Q.24 The pKa values for the three acidic group P, Q, R are 4.3, 9.7 and 2.2 respectively

(R) (P)
HOOC–CH –CH2 – COOH

NH3
(Q)
Calculate the isoelectric point of the amino acid?

Q.25 How will you separate?

(a) Ethane, Ethene & Ethyne (b) 1-Butyne and 2-Butyne

IR
(c) 2-hexyne and 3-hyxyne (d) Phenol & Propanol
(e) 2-Propanol and Propanone (f) CH3COOH & HCOOCH3
(g) PhOH & PhCOOH (h) EtOH & EtNH2
(i) EtNH2 & Me2NH (j) EtOH & Et– O –Et
Q.26 How will you differentiate?
(a) Propane and Propene (b) 1-Butyne and 2-Butyne
(c) 2- Hexyne and 3-hexyne (d) 1,1-Dichloroethane and 1,2-Dichloroethane
(e) Chloroethane and Chloroethene (f) Pure and Oxidized CHCl 3
.S
(g) p-chlorotoluene and benzylchloride (h) n- propylchloride and isopropylchloride
(i) Methanol and ethanol(j) Isobutanol and tert-butanol
(k) 2- Pentanol and 3-pentanol (l) O-cresol and benzylalcohol
(m) Ethanol and Propanol (n) Propanone and Ethanol
(o) HCHO and PhCHO (p) Glucose and Fructose
(q) HCOOH & CH3COOH (r) HCOOH & HCHO
CH3
CH2NH2
&
.J

(s) MeNH2 & Me2NH (t)

NH2
EXERCISE IV

Q.1 Give the structures of the products in each of the following reactions. [JEE 2000]
N

H
(i) Sucrose 
 A + B
NOH
H Polymerisation
(ii)  C     
  [–D –]n

Q.2 Aspartame, an artificial sweetener, is a peptide and has the following structure:[JEE 2001]
CH2 – C6H5
H2N – CH – CONH – CH – COOCH3
CH2 – COOH
(i) Identify the four functional groups.
(ii) Write the zwitterionic structure
(iii) Write the structures of the amino acids obtained from the hydrolysis of aspartame.
(iv) Which of the two amino acids is more hydrophobic?

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Q.3 Following two amino acids lysine and glutamine form dipeptide linkage. What are two possible dipeptides?
[JEE 2003]
NH2 NH2

H2N COOH + HOOC COOH

Q.4 The structure of D-Glucose is as follows- [JEE 2004]
(a) Draw the structure of L-Glucose
(b) Give the reaction of L-Glucose with Tollen's reagent
CHO
H OH
OH H
H OH
H OH

HO

IR
Q.5 Which of the following pairs give positive Tollen's test? [JEE 2004]
(A) Glucose, sucrose (B) Glucose, fructose
(C) Hexanal, Acetophenone (D) Fructose, sucrose

Q.6 Two forms of D-glucopyranose, are called

(A) Enantiomers (B) Anomers
(C) Epimers (D) Diastereomers

Q.7
.S
Monomer A of a polymer on ozonolysis yields two moles of HCHO and one mole of CH3COCHO
[JEE 2005]
(a) Deduce the structure of A
(b) Write the structure of "all cis"-forms of polymer of compound A.

Q.8 When benzene sulfonic acid and p-nitrophenol are treated with NaHCO3, the gases released respectively are-
[JEE 2006]
(A) SO2, NO2 (B) SO2, NO
(C) SO2, CO2 (D) CO2, CO2
.J

Q.9 Statement-I : Glucose gives a reddish-brown precipitate with Fehling's solution.

because [JEE 2007]
Statement-II : Reaction of glucose with Fehling's solution gives CuO and gluconic acid.
(A) Statement- I is true, Statement- II is true and Statement- II is correct explanation for
Statement- I
N

(B) Statement- I is true, Statement- II is true and Statement- II is NOT a correct explanation for Statement- I
(C) Statement- I is true, Statement- II is false.
(D) Statement- I is false, Statement- II is true.

Q.10 Statement-I : p-ydroxybenzoic acid has a lower boiling point than o-hydroxybenzoic acid.
because [JEE 2007]
Statement-II : o-Hydroxybenzoic acid has Intramolecular hydrogen bonding.
(A) Statement- I is true, Statement- II is true and Statement- II is correct explanation for
Statement- I
(B) Statement- I is true, Statement- II is true and Statement- II is NOT a correct explanation
for Statement- I
(C) Statement- I is true, Statement- II is false.
(D) Statement- I is false, Statement- II is true.

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Mob. No. : 9214233360
Q.11 Match the chemical substances in Column I with type of polymers/type of bonds in
Column-II. Indicate your answer by darkening the appropriate bubbles of the 4 × 4 matrix given in the ORS.
[JEE 2007]
Column-I Column-II
(A) Cellulose (P) Natural polymer
(B) Nylon-6,6 (Q) Synthetic polymer
(C) Protein (R) amide linkage
(D) Sucrose (S) Glycoside linkage

Q.12 Match the compounds/ion in column I with their properties/reaction in Column-II. Indicate your answer by
darkening the appropriate bubbles of the 4 × 4 matrix given in the ORS.
[JEE 2007]
Column-I Column-II
(A) C6H5CHO (P) gives precipitate with
2,4-dinitrophenylhydrazine
(B) CH3C  CH (Q) gives precipitate with AgNO3
–
(C) CN (R) is a nucleophile
–
(D) I (S) is involved in cyanohydrin formation

Q.13 Cellulose upon acetylation with excess acetic anhydride/H2SO4 (catalytic) gives cellulose triacetate whose

IR
structure is [JEE 2008]
AcO AcO
OO ) OO )
AcO H H AcO H H
OAc H OH H
AcO O O H AcO O O H
H H H H
OAc H H OAc OH H H OH
H O O H H O O H
(A) H (B) H
OAc H H OAc OH H H OH
( O H ( O H
H OAc
.S H OH
AcO AcO AcO AcO AcO AcO

H OH H OH H OO ) H OH H OH H OO )
H H H H H H
(C) OAc H OAc H OAcH (D) H H H H H H
( O O O ( O O O
H H
H OAc H OAc H OAc OAc OAc OAc OAc OAc OAc

Q.14 Match the compounds in Column I with their characteristic test(s)/reaction(s) given in Column II. Indicate your
.J

answer by darkening the appropriate bubbles of the 4 × 4 matrix given in the ORS.
[JEE 2008]
Column-I Column II
 
(A) H2N – NH3Cl (P) Sodium fusion extract of the compound
gives Prussian blue colour with FeSO4
N

 
NH3I
(B) HO (Q) gives positive FeCl3 test
COOH

 
(C) HO NH3Cl (R) gives white precipitate with AgNO3

 
O2N NH– NH3Br
(D) (S) reacts with aldehydes to form the

NO2
corresponding hydrazine derivative

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ETOOS Education Pvt. Ltd.

Plot No. 68, Near Union Bank of India, Rajeev Gandhi Nagar, Kota, Rajasthan – 324005
Mob. No. : 9214233360
Q.15 The correct statement(s) about the following sugars X and Y is(are)- [JEE 2009]

CH2OH
CH2OH H O H
H O H HOH2C O H
H CH2OH H HO
H
OH H H O O OH
O
HO H HO CH2OH H OH H
OH H
H OH H
HO
OH H
H OH
(X) (Y)

(A) X is a reducing sugar and Y is a non-reducing sugar

(B) X is a non-reducing sugar and Y is a reducing sugar
(C) The glucosidic linkages in X and Y are  and , respectively
(D) The glucosidic linkages in X and Y are  and , respectively

Q.16 Among cellulose, poly(vinyl chloride), nylon and natural rubber, the polymer in which the intermolecular force
of attraction is weakest is [JEE 2009]
(A) Nylon (B) Poly (vinyl chloride)

IR
(C) Cellulose (D) Natural Rubber

Q.17 The correct statement about the following disaccharide is – (JEE2010)

CH2OH

H O HOH2C H
H
H
.S H HO
OH H OCH2CH2 O CH2OH
HO
H OH
OH H
(A) Ring (a) is pyranonse with -glycosidic link
(B) Ring (a) is furanonse with -glycosidic link
(C) Ring (b) is furanonse with -glycosidic link
(D) Ring (b) is pyranonse with -glycosidic link
.J

Q.18 A decapeptide (Mol. Wt. 796) on complete hydrolysis gives glycine (Mol. wt. 75), alanine and phenylalanine.
Glycine contributes 47.0% to the total weight of the hydrolysed products. The number of glycine units present
in the decapeptide is – (JEE2011)
N

Q.19 The following carbohydrate is -

H
OH H
HO O
HO OH
H OH
H H
(A) ketohexose (B) an aldohexose
(C) an -furanose (D) an -pyranose

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ETOOS Education Pvt. Ltd.

Plot No. 68, Near Union Bank of India, Rajeev Gandhi Nagar, Kota, Rajasthan – 324005
Mob. No. : 9214233360
 ANSWER KEY
EXERCISE-1

[Link]. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16
Ans. D A C D A C B D A D A B C C C D
[Link]. 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32
Ans. C A C D D C A C C D B A B B B D

EXERCISE-II
[Link]. 1 2 3 4 5 6 7 8 9 10 11
Ans. A,B,C A,B,C,D A,B,C A,B,D A,B,C A,B,D A,B,C,D B,C,D A,B,C A,C,D A,B,C
[Link]. 12 13 14 15 16 17 A B C D
18
Ans. B,C A,B,C,D A,B,C A,B,C B,D B,D P,Q,S S R R
[Link]. A B C D A B C D
19 20
Ans. S R P Q Q P R S

IR
EXERCISE-III

[Link]. 1 2 3 4 5 6 7 8 9 10 11
Ans. A A A A A A D B B D C
[Link]. 12 13 14 A B C D
15
Ans. C A C Q,R P,S R S
A B C D A B C D
16 17
R
.S S P Q Q,S Q,S P,R,T,U P,S,T,U
A B C D A B C D
18 19
P,Q,R P P P,Q,R Q,P P S T
A B C D A B C D
20 21
P,Q,R S R P,Q,S 1-Q 1,2-P 1-S 3-R
A B C
22
S-X P-Y,R-X Q-Z

–
CHO COOH COO
CO
.J

HO H HO H H OH
Br2 N H OH
H OH H OH H OH O
H OH
H OH H OH H OH
H
CH2OH CH2OH CH2OH
CH2OH
(A) (B) (C)
Q.23
N

CHO
H OH
Na
H OH
Hg
H OH
CH2OH
(D)

Q.24 3.25

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ETOOS Education Pvt. Ltd.

Plot No. 68, Near Union Bank of India, Rajeev Gandhi Nagar, Kota, Rajasthan – 324005
Mob. No. : 9214233360
 EXERCISE IV
Q.2 (i) Amine, carboxylic acid, Amide, Ester

O O
CHO
H OH H OH
+2
HO H Ag(NH3) HO H
Q.4 H OH H OH
HO H HO H

HO (L-glucose) HO

Q.5 B Q.6 B
CH3 O
O O
Q.7 (a)

IR
CH2 Ozonolysis
+
H2C H H
H3C H
H3C H CH2 H3C H
CH2
(b) CH3 CH2
H3C H
.S
Q.8 D
Q.9 C Q.10 D

Q.11 (A) P, S; (B) Q, R; (C) P, R; (D) S

Q.12 (A) P, S ; (B) Q; (C) Q, R, S ; (D) Q, R
Q.13 A
Q.14 (A) R, S (B) P,Q (C) P, Q, R (D) P, S
.J

Q.15 B, C
Q.16 D
Q.17. (A)
Q.18. (6)
Sol. For n-units of glycine,
N

n  75
 100  47
(796  9  18)

n=6
Q.19. (B)
Sol.
H
OH H
HO O
HO OH
H OH
H H
-pyranose
(Aldohexose)

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ETOOS Education Pvt. Ltd.

Plot No. 68, Near Union Bank of India, Rajeev Gandhi Nagar, Kota, Rajasthan – 324005
Mob. No. : 9214233360