Chemistry : Biomolecules and Polymers

SECTION - I
SUBJECTIVE TYPE PROBLEMS
Problem 1 : Write the monomer units of Bakellite?
Solution : Phenol and formaldehyde.
Problem 2: Name a synthetic polymer which is an ester.
Solution : Dacron or Terylene.
Problem 3: Write the hemiacetal formation for Glucose.

OH OH
OH
H

O O
HO H O
H H H
H H H H
Solution :
O
OH
H OH H
OH H OH H OH
OH OH
New
Stereocenter New
H OH
H OH H OH Stereocenter
D(+)-glucofuranose D(+)-glucose D(+)-glucopyranose
less stable more stable

Problem 4 : The pKa of the carboxyl group in an amino acid valine, (CH3)2CHCH(NH2)(COOH)
is 2.31 and the pKa for the amino group of the same amino acid is 9.69. Compute the
isolectric point (pI) for valine and draw the structure of this amino acid when the pH
of the solution equals to pI. Also draw the structures of valine that predominate at
pH = 2 and pOH = 2.
Solution : The isoelectric point (pI) is the pH at which the amino acid exists only as a dipolar ion with
net charge zero.

At isoelectric point, for a neutral amino acid, pI 

 pK a1  pK a 2 
2
The dissociation of cationic form of valine can be represented as

- -
O 2C H CO 2 CO 2
(pK a1 ) (pK a2 )
HC NH3 HC NH3 HC NH2
OH  OH 

HC (CH3 )2 H HC (CH3 ) 2 H HC (CH3 ) 2

Netcharge (+1) (0) (-1)

The species with zero net charge exists between species with (+1) and (–1) net charges.

pI 
 pK a1  pK a 2   9.69  2.31  6
2 2
 Chemistry : Biomolecules and Polymers

-
CO2

When the pH of the solution equals to pI, the structure of valine is HC NH3

HC (CH3)2
CO2 H

When the pH of the solution is two, the structure of valine is HC NH3

HC (CH3 )2
-
CO2

When the pH of the solution is 12, the structure of valine is HC NH2

HC (CH3 )2
Problem 5 : Convert

O C
O
H2 C OH HC OH

C O HC OH

HC
(CHOH)3
HC OH
H2 C OH
H2C OH
O C OH

H2C OH HC OH O C
H2C OH O
HC OH
C O HC OH
 , -H 2O
Solution : Ni / H 2
  (CHOH)4
HNO3
   HC OH
(CHOH)3 HC OH
HC
H2C OH
H2C OH HC OH HC OH

H2C OH H2C OH

Problem 6 : (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

HO3 S NH2 O3 S NH3

The weakly acidic –+NH3 transfers H+ to OH– to form a soluble salt, P–NH2–C6H4
SO3 Na+ on the other hand – SO3 is too weakly basic to accept H+ from strong acids.
(ii) Due to its ionic character it is insoluble in organic solvents.
Chemistry : Biomolecules and Polymers

Problem 7 : Compound (A) C5H10O5, give a tetra-acetate with Ac2O and oxidation of (A) with Br2
– H2O gives an acid, C5H10O6. Reduction of (A) with HI and red phosphorous gives
3-methylbutane. What is structure of (A)?
Solution : The formation of tetracetate indicates of 4 OH groups and oxidation with bromine water
indicates presence of CHO group. Reduction with red phosphorus and HI indicates presence
of one carbon in the side chain. Thus, the structure of (A) would be

CHO

HC OH

HO CH2 C OH

H2C OH

Problem 8 : (a) What is the structure of nylon-6, made by alkaline polymerisation of caprolactum?

N
H

(b) Suggest a mechanism for the process. Is polymerisation of the chain reaction or
step reaction type?

H O

Solution : (a) N
N

H O

NH
Base
(b)
Base N
O H

NH
Base N
O H
O H

N
etc.
Base NH

O
 Chemistry : Biomolecules and Polymers

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.
Problem 9 : 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).

H H H H H Cl H Cl

Solution :

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 together
poorly.
Poly (vinylidene chlroide) has two identical substituents on each carbon and the chains fit
together well.
Problem 10 : Supply structures for H through K. Given :
An aldohexose NH2 OH/base Ac 2 O/NaOAc  HOAC NaOMe/MeOH
  H   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.
Solution : (a) H is an oxime HOCH2(CHOH)4CH = NOH; I is the completely acetylated oxime,
AcOCH 2 (CHOAc) 4 CH = NOAc that loses 1 mole of HOAc to for m 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.
Chemistry : Biomolecules and Polymers

SECTION - II
SINGLE CHOICE PROBLEMS
Problem 1 : Starch is polymer of
(a) Fructose (b) Glucose
(c) Lactose (d) None
Solution : Starch is homopolysaccharide of glucose.
And. (b)
Problem 2 : The commonest disaccharide has the molecular formula
(a) C10H18O9 (b) C10H20O10
(c) C11H22O11 (d) C12H22O11
Solution : The most common disaccharide is sucrose, whose molecular formula is C12H22O11.
Ans. (d)
O
 || 
Problem 3 : The structure of glycine (amino acid) is H3 N CH 2 C O (Zwitter ion)
Select the correct statement of the following.
(a) Glycine, as well as other amino acids are amphoteric.

(b) The acidic functional group in amino acids is  N H
3

(c) The basic functional group in amino acids is CO 2

(d) All the statements are correct
Solution : Glycine and all other amino acids are amphoteric because of the presence of NH2 and

CO2H group both. The amino acid exists and Zwitter ion and acidic group is  N H while
3

basic group is CO 2 .

Ans. (d)
Problem 4 : Sugars are characterised by the preparation of osazone derivatives. Which sugar
have identical osazones.
(a) Glucose and lactose (b) Glucose and fructose
(c) Glucose and arabinose (d) Glucose and maltose
Solution : The reaction with phenyl hydrazone gives same osazone because glucose and fructose
differ only on carbon atoms 1 and 2 which are involved in osazone formation.
Ans. (b)
Problem 5 : Cane sugar on hydrolysis yields
(a) Glucose and maltose (b) Glucose and lactose
(c) Glucose and fructose (d) Only glucose
 Chemistry : Biomolecules and Polymers

HOH
Solution : C12 H 22 O11 
H |
 C6 H12O 6  C6 H12O6
Glucose Fructose

The process is known as inversion of cane sugar.

Ans. (c)
Problem 6 : Sucrose on hydrolysis yields a mixture which is
(a) Optically inactive (b) Dextrorotatory
(c) Laevorotatory (d) Racemic
Solution : Sucrose on hydrolysis yields equimolar mixture of D-(–)-fructose and D-(+)-glycose. Since
specific rotation of (–)-fructose is greater than (+)-glucose D the mixture is laevorotatory.
Ans. (c)
Problem 7 : A high molecular weight molecule which does not contain repeating structural units is
called a
(a) Polymer (b) Macromolecule
(c) Both (a) and (b) (d) None of these
Solution : A polymer has always repeating structural units derived from monomer. For example proteins
and nucleic acid are regarded as macromolecules, but not polymers because their molecules
do not contain repeating structural units. All polymers are macromolecules, but all
macromolecules are not polymers.
Ans. (b)
Problem 8 : The force of attraction between the neighbouring peptide chains is
(a) van der Waal’s force (b) Covalent bond
(c) Hydrogen bond (d) Peptide linkage
Solution : Neighbouring peptide chains are held by hydrogen bonds between – CO – and –– NH ––.
Ans. (c)
Problem 9 : Peptides on hydrolysis give
(a) Ammonia (b) Amines
(c) Amino acids (d) Hydroxy acids
Solution : Peptides are formed by condensation of -amino acids. Therefore, on hydrolysis they yield
-amino acids.
Ans. (c)
Problem 10 : An example of a condensation polymer is
(a) PVC (b) terylene
(c) polypropylene (d) polystyrene
Solution : In condensation polymerization, a series of condensation reactions between the (generally
two) monomers containing atleast two functional groups each occur with the loss of a small
molecule such as H2O, CH­3OH or HX (X = halogen). Terylene is a condensation polymer
of ethylene glycol and terephthalic acid.
Ans. (b)
Chemistry : Biomolecules and Polymers

SECTION - III
MULTIPLE CHOICE PROBLEMS
Problem 1: Which of the following pairs contain only reducing carbohydrates?
(a) Glucose, maltose (b) Fructose, lactose
(c) Sucrose, starch (d) Galactose, cellulose
Solution : Glucose, maltose, fructose and lactose are reducing carbohydrates.
Ans. (a, b)
Problem 2: Which of the following are biopolymers?
(a) Nucleic acids (b) Leather
(c) Bakelite (d) Orlon
Solution : Nucleic acids and leather are biopolymers.
Ans. (a, b)
Problem 3: Which of the following has a glucosidic linkage?
(a) Sucrose (b) Amylose
(c) Galactose (d) Maltose
Solution : Sucrose, amylose and maltose have a glucosidic linkage.
Ans. (a, b, d)
Problem 4: Which of the following carbohydrates exhibit mutarotation?
(a) Glucose (b) Fructose
(c) Maltose (d) Galactose
Solution : All are exhibit mutarotation
Ans. (a, b, c, d)
Problem 5: Which of the following contain disulphide bridges?
(a) Haemoglobin (b) Insulin
(c) Oxytocin (d) Vasopressin
Solution : Insulin, orytocin and vasopressin contain disulphide bridges.
Ans. (b, c, d)
Problem 6: The essential amino acids are :
(a) glycine (b) alanine
(c) valine (d) leucine
Solution : Valine and leucine are essential amino acids.
Ans. (c, d)
Problem 7: Glucose and fructose gives same type of reactions :
(a) with phenyl hydrazine (b) on reduction with Na–Hg/H2O
(c) with Fehling’s solution (d) warming with dilute alkali
Solution : (a, c, d) give same reaction with glucose and fructose
Ans. (a, c, d)
 Chemistry : Biomolecules and Polymers

Problem 8: Mutarotation is shown by :

(a) glucose (b) fructose
(c) sucrose (d) starch
Solution : Glucose and fructose show mutarotation
Ans. (a, b)
Problem 9: Raffinose on hydrolysis gives :
(a) mannose (b) fructose
(c) glucose (d) glactose
Solution : Raffinose on hydrolysis gives fructose, glucose and glactose
Ans. (b, c, d)
Problem 10: The disaccharides (C12H22O11) are :
(a) cane sugar (b) raffinose
(c) lactose (d) maltose
Solution : Cane sugar, lactose and maltose are disaccharides.
Ans. (a, c, d)
Chemistry : Biomolecules and Polymers

MISCELLANEOUS PROBLEMS
SECTION - IV
COMPREHENSION TYPE PROBLEMS

Write up – I
Monosaccharides are oxidized by a variety of reagents. The aldehyde group of an aldose oxidize the
terminal - CH2OH group at the far end of the molecule. Oxidation is used to identify the functional
groups of a sugar, to help to determine its stereochemistry, and as part of a synthesis to convert on
sugar into another.
Bromine water oxidizes the aldehyde group of an aldose to a carboxylic acid. It does not oxidize the
alcohol groups of the sugar and it does not oxidize ketones. Also, bromine water is acidic and does not
cause epimerization or rearrangement of the carbonyl group.
Nitric acid is a stronger oxidizing agent than bromine water, oxidizing both the aldehyde and the terminal
-CH2OH group of an aldose to carboxylic acid groups. In its open-chain form an aldose has an aldehyde
group, which reacts with Tollens reagent to give a silver mirror are called reducing sugars. Tollens test
cannot distinguish between aldoses and ketoses because the basic tollens basic conditions, the open
chain form of a ketose can isomerize to an aldose, which reacts to give a positive Tollens test.
Periodic acid oxidise both aldoses and ketoses, because of presence of successive OH groups or OH
and C = O groups. This is also use for determination of size of carbohydrate chain.

CHO
H OH Br2 / H 2O
Problem 1 : 
HO H
CH2 OH

Product is

COOH COOH
H OH H OH
(a) HO H (b) HO H
COOH CH2 OH

COOH COOH
H OH
(c) H OH (d)
COOH CH2 OH

Solution : Bromine water oxidizes the aldehyde group of an aldose to carboxylic acid. It does not
oxidise the alcohol groups of the sugar.
Ans. (b)
Problem 2 : Which of the following test can distinguish aldoses and ketoses
(a) Bromine water oxidation (b) Periodic acid oxidation
(c) Tollens Test (d) Both (a) and (b)
 Chemistry : Biomolecules and Polymers

Solution : Bromine water oxidises the aldehyde group of an aldose to carboxylic acid it does not oxidise
ketones.
Ans. (a)
Problem 3 : Which one is true about reducing sugars ?
(a) Sugar containing aldehyde group only
(b) Sugar contains acital form in cyclic state
(c) Reducing sugar react with Tollens reagent
(d) Sugar reduced by any reducing agent
Solution : Reducing sugar react with Tollen’s reagent.
Ans. (c)

Write up – II
A polymer is a large molecule composed of many smaller repeating units (the monomers) bonded
together. There are two major classes of polymers : addition polymers and condensation polymers.
Addition polymers results from rapid addition of one molecule at a time to growing polymer chain. It
also sometimes called chain growth polymers because growth usually occurs at the end of a chain.
Condensation polymers result from condensation (bond formation with loss of small molecule) between
the monomers. The most common condensation involve the formation of amide and esters. In a
condensation polymerisation, any two molecules can condense; they do not need to be at the end of a
chain. Condensation polymers are sometimes called step-growth polymers because any pair of monomer
molecules can react to give a step in the condensation.
Many alkenes undergo chain-growth polymerisation when treated with small amounts of suitable initiators.
Natural rubber is isolated from a white fluid called latex. Like many other plant products, natural
rubber is a terpene composed of isoprene units when natural rubber is heated with sulfur the process is
called vulcanisation and vulcanized rubber has much greater toughness and elasticity than natural
rubber. It withstands relatively high temperatures without softening and it remains elastic and flexible
when cold.
Problem 4 : The monomer of Teflon is
(a) H2C = CHCl (b) F2C = CF2
(c) H2C = CHPh (d) CH2 = CHCH3
Polymerisation
Solution : nCF2  CF2  —
( CF2 — CF2 —
)n
Teflon
Ans. (b)
Problem 5 : Vulcanisation of natural rubber is done by
(a) C (b) Si
(c) S (d) P
Solution : Sulphur
Ans. (c)
Problem 6 : Which is not correct about the vulcanised rubber
(a) It is more elastic than natural rubber
(b) It obtained directly from plant
(c) It withstands relatively high temperature than natural rubber.
(d) It has much greater toughness than natural rubber
Solution : a, c, d are correct for valcanised rubber.
Ans. (b)
Chemistry : Biomolecules and Polymers

MATCHING TYPE PROBLEM

7. Column (I) Column (II)

(a) Buna-S (p) Isoprene
(b) Bakelite (q) Caprolactum
(c) Nylon-6 (r) Butadiene and styrene
(d) Natural rubber (s) Phenol and formaldehyde
Sol. Constituents of Buna-S are Butadiene and styrene.
Constituents of Bakelite are Phenol and formaldehyde
Constituents of Nylon-6 is caprolactum
Constituents of Natural rubber is isoprene
Ans. (a) — (r) (b) — (s)
(c) — (q) (d) — (p)

ASSERTION-REASON TYPE PROBLEMS

The question given below consist of an ASSERTION and the REASON. Use the following key for the
appropriate answers
(a) If both Assertion and Reason are correct and Reason is the correct explanation for Assertion
(b) If both Assertion and Reason are correct and Reason is not the correct explanation for
Assertion
(c) If Assertion is correct but Reason is not correct.
(d) If Assertion is incorrect but Reason is correct.
8. Assertion : Starch and cellulose reduce Tollen's reagent.
Reason : Starch and cellulose on hydrolysis give hundreds to thousands of monosaccharides molecules.
Solution : Assertion is false but reason is true.
Although starch and cellulcose both contain an aldehydic group at the end of the chain but
still they do not reduce Tollen’s reagent. The reason being that due to high molecular weights
of these polysaccharides, their reducing properties are masked and hence no detectable
reducing, properties areobserved.
Ans. (d)
9. Assertion : Acid or enzymatic hydrolysis of sucrose to give an equimolar mixture of glucose and fructose
is called inversion.
Reason : Sucrose is the only naturally occurring disaccharide which is reducing.
Solution : Both assertion and reason are true but reason is not the correct explanation of assertion.
Sucrose is dextrorotatory while an equimolecular mixture of glucose and fructose which it
gives on hydrolysis is laevorotatory. Inversion of sign of optical rotation has occurred during
hydrolysis thus this hydrolysis is called inversion.
Ans. (b)
10.Assertion : Glucose is used in silvering of mirros.
Reason : Glucose is less acidic than a monohydric alcohol.
Solution : Assertion is true but reason is false.
Ka for glucose is 6.6 × 10–12 and Ka for C2H5OH is 7.4 × 10–20. Thus glucose is more acidic
than a monohydric alcohol.
Ans. (c)