Biomolecules Part 01

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• molecules seen in living organisms , essential for their biological

processes.
• carbon-based molecules along with O , H , N and sometimes
bio-metals too.
• 4 types of biomolecules .
• Carbohydrates 2. Proteins 3. Lipids 4. Nucleic acids
• Carbohydrates are optically active polyhydroxy aldehydes or optically
active polyhydroxy ketones or any compound which on hydrolysis,
gives optically active polyhydroxy aldehydes or optically active
polyhydroxy ketones
• Carbohydrates contain C , H , O ( rarely with N , S , P .)
• Carbohydrates have OH groups which form hydrogen bonding with
the water molecules . Hence carbohydrates are soluble in water.
• the minimum number of Carbon atoms necessary to form a
carbohydrate = 3.
• carbohydrates seen stored in plants. : starch , cellulose , starch…
• carbohydrate seen stored in animals. : glycogen ( animal starch )
• carbohydrate seen in wood. : cellulose
• carbohydrates are often called saccharides.(sugar ), although not all
the saccharides are sweet.
• The simplest carbohydrates are called monosaccharides, or simple
sugars.
• They are the monomers for the synthesis of polymers or complex
carbohydrates.
• Monosaccharides are carbohydrates that cannot be hydrolysed
further. Eg: Glucose , Fructose.
• Monosaccharides containing an aldehyde group are known as
aldoses.
• Monosaccharides containing a keto group are known as ketoses.
• Monosaccharides are classified based on the number of carbons in the
molecule.
• identified using a prefix that indicates the number of carbons and the
suffix –ose, which indicates a saccharide.
• triose (three carbons), tetrose (four carbons), pentose (five carbons),
and hexose (six carbons)
• a ketose containing 3 carbon atoms is called ketotriose
• an aldose containing 3 carbon atoms is called aldotriose
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• The hexose D-glucose is the most abundant monosaccharide in
nature.

Isomers in carbohydrates :

• Trioses (C3H6O3)
Glyceraldehyde and dihydroxyacetone ( aldotriose and ketotriose )

• Pentoses (C5H10O5)
D – ribose , l – arabinose and D – xylose ( aldopentoses )

• Hexose (C6H12O6)
D – glucose and L – fructose

Aldohexoses which have the same configuration as that of the D- form of


Glyceraldehyde → D- Sugars.

Aldohexoses which have the same configuration as that of the L- form of


Glyceraldehyde → L- Sugars.

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Hence Glucose ( C6H12O6 ) has :

D – Glyceraldehyde D – Glucose

L – Glyceraldehyde L – Glucose

D- and L- notation is used to designate enantiomers.


Has no connection with the optical rotation.

D-glucose is the enantiomer of L-glucose.


D and L represent the configuration of the molecule.

In the Fischer model ( open chain structure ) of glucose :

if the OH on the bottom chiral centre points to the right, it is referred to


as D-glucose

if the OH on the bottom chiral centre points to the left, it is referred to


as L-glucose
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Q 1. What are carbohydrates ?
Ans :
Carbohydrates are optically active polyhydroxy aldehydes or optically
active polyhydroxy ketones or any compound which on hydrolysis gives
optically active units.

Q 2. Why are carbohydrates soluble in water ?


Ans: Carbohydrates have OH groups that form hydrogen bonds with water
molecules.

Q 3. Name some of the carbohydrates seen stored in plants.


Ans: starch , cellulose …

Q 4. Name a carbohydrate seen stored in animals. Ans: glycogen ( animal


starch )

Q 5. Name a carbohydrate seen in wood.


Ans : cellulose

Q 6.What is the minimum number of Carbon atoms necessary to form a


carbohydrate? Why?
Ans : ……………..3
Reason : a carbohydrate is a polyhydroxy aldehyde or ketone.
So, if it contains less than 3 carbon atoms, it can not have more than one
hydroxyl group and a carbonyl group simultaneously.

Q 7. How are Carbohydrates classified ?


Ans :
A . Based on the nature of the carbohydrate towards hydrolysis.
(1) whether they hydrolyse
(2) no: of products after hydrolysis.
Hence :
Monosaccharides , Oligosaccharides ( Disaccharides and Trisaccharides ) ,
Polysaccharides.
B. Based on their reducing or non-reducing nature.
Hence :
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Reducing sugars and Non-reducing sugars.
Q 8. What are monosaccharides ? [ End Exercises. 14.1 ]
Ans : Monosaccharides are carbohydrates that cannot be hydrolysed
further.
Eg : Glucose , Fructose.

Q 9. How are monosaccharides classified ?


Ans :

Monosaccharides are classified on the basis of number of carbon atoms and


the type of functional group present in them.

❖ Monosaccharides containing an aldehyde group are known as aldoses.


❖ Monosaccharides containing a keto group are known as ketoses.

Monosaccharides are further classified as trioses, tetroses, pentoses,


hexoses, and heptoses according to the number of carbon atoms they
contain.
Hence :

❖ a ketose containing 3 carbon atoms is called ketotriose.


❖ an aldose containing 3 carbon atoms is called aldotriose.

Q 10. What are Oligosaccharides ?


Ans : Oligosaccharides are those carbohydrates which on hydrolysis give
many monosaccharide units.

Q 11. How are Oligosaccharides classified ?


Ans : Oligosaccharides are broadly classified into Disaccharides and
Polysaccharides.

Q 12. What are Disaccharides ?


Ans : Disaccharides are carbohydrates which on hydrolysis give 2 similar or
2 dissimilar monosaccharide units.
Eg : Sucrose on hydrolysis gives glucose + fructose.
Maltose on hydrolysis gives two glucose units
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Q 13. What are Polysaccharides ?
Ans : Polysaccharides are carbohydrates which on hydrolysis give a large
number of monosaccharide units.
Eg : starch , cellulose , glycogen.

Q 14. What are Reducing and Non-reducing sugars ? [End Exercises.14.2 ]


Ans :

Reducing sugars :
Carbohydrates which reduce Tollen’s reagent and Fehling’s solution.
Such carbohydrates will have their functional groups free.
Eg : all monosaccharides ( glucose , fructose ) , certain disaccharides ,
having free functional groups like Maltose , Lactose.

Non-reducing sugars : Carbohydrates which cannot reduce Tollen’s reagent


and Fehling’s solution.
Such carbohydrates will not have free functional groups .
Eg: all polysaccharides ( starch ) , disaccharide ( sucrose )

Q 15. Write two main functions of carbohydrates in plants.


[ End Exercises. 14.3 ]

Ans : The two main functions of carbohydrates in plants are:


(i) Polysaccharides such as starch serve as storage molecules.
(ii) Cellulose, a polysaccharide, is used to build the cell wall.

Q 16. Classify the following into monosaccharides and disaccharides.


Ribose, 2-deoxyribose, maltose, galactose, fructose and lactose.
[ End Exercise. 14.4 ]

Ans:
Monosaccharides: Ribose, 2-deoxyribose, galactose, fructose
Disaccharides: Maltose, lactose

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Q 17 . Glucose or sucrose are soluble in water but cyclohexane or benzene
(simple six membered ring compounds) are insoluble in water. Explain.
[ In-text Question. 14.1 ]
Ans:
If a compound has to be water soluble, it should develop dipoles.
This would result in the formation of a hydrogen bonding between the
water molecule & the compound.

Glucose and Sucrose molecules have –OH groups.


Hence they undergo extensive Hydrogen bonding with water.
Hence, these are soluble in water.

But cyclohexane and benzene do not contain −OH groups.


They contain only carbon & hydrogen atoms.
As a result the dipole developed is very weak in nature & hence the
hydrogen bonding formed is not strong.
Hence, they cannot undergo Hydrogen bonding with water and as a result,
are insoluble in water.

Q 18 . Why are all Monosaccharides considered as Reducing sugars ?


Ans :
Monosaccharides having an aldehyde group ( --CHO ) are called Aldoses.
Monosaccharides having a ketone group ( --CO -- ) are called Ketoses.

The aldehydic group in aldoses are easily oxidised. This happens through a
redox process.
So the Aldose gets oxidised and the weak oxidising agent gets reduced.
Hence, all Aldoses are Reducing sugars.

The ketonic group in Ketoses in aqueous solutions forms a molecule with


an aldehyde group.
This happens through a process called as Tautomerization .
Once formed , the molecule can be oxidised through a redox reaction.

Hence Ketoses are Reducing sugars , although it is the isomer of the ketone
having the aldehyde which is the Reducing sugar.
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The Ketone by itself cannot undergo oxidation without getting decomposed.
Hence all Monosaccharides are considered as Reducing sugars
Q 19 . Distinguish between Aldoses and Ketoses.
Ans :
Aldoses are monosaccharides having the – CHO at C1
Ketoses are monosaccharides having the – CO -- at C2

Q 20. What is the simplest aldose ? Draw its structural formula .


Ans :

The simplest aldose is a carbohydrate having 3 carbon atoms.


Called as Aldotriose.

Hence, an Aldotriose is a monosaccharide having an aldehyde (an aldose)


at C1 and a total of three carbon atoms. (a triose).

Hence Glyceraldehyde is the simplest aldose.

The structural formula of Glyceraldehyde is :

Q 21 . Why is Glyceraldehyde an optically active compound ?


Ans :
An optically active compound is a molecule having an asymmetric carbon
atom.
{ Asymmetric carbon atom is a carbon atom to which 4 different atoms /
groups of atoms attached }.

Glyceraldehyde has an asymmetric carbon atom at C2 . 1


Hence it is optically active.

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Q 22. What are stereoisomers ?
Ans : Stereoisomers are molecules with the same molecular formula and
sequence of the bonded atoms , but will differ in the positioning of their
atoms in space.

The difference between stereoisomers can only be seen when the three-
dimensional arrangement of the molecules are viewed.

Q 23. Represent the stereoisomers of Glyceraldehyde .


Ans :

and

Q 24. How are stereoisomers named ?


Ans : The stereoisomers of a compound are named by defining the
stereochemical configuration of a stereo-center in the molecule by
designating R and S prefixes to the IUPAC name of the compound.
R for a clockwise orientation of the groups at the stereocentre.
S for an anti clockwise orientation of the groups at the stereocentre.

Q 25. How can the number of stereoisomers of a given compound be


determined ?
Ans :
The maximum number of stereoisomers of a given saturated compound is
determined by the formula 2n where n = number of asymmetric carbon
atoms present in the compound.

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Q 26 . What are Enantiomers ?
Ans :
Enantiomers are :
(a) They are Stereoisomers
(b) They are mirror images of each other
(c) They are non-superimposable ( they are chiral molecules )
(d) The pair will differ in the configuration at the asymmetric carbon.
(e) They rotate the plane of a polarised light to equal , but opposite angles.
(f) They will interact with other chiral molecules differently.
(g) in the presence of an achiral environment , they exhibit identical
physical and chemical properties.

(+) enantiomers :
rotate light in a clockwise direction.

( dextro rotation) , ( towards the right ) , ( d )

(-) enantiomers :
rotate light in an anti-clockwise direction.
(laevo rotation ) ,(towards the left ) , ( l )

……note : the (d) and (l) are not used these days……
they are not accepted by IUPAC.

Q 27 . Why are the stereoisomers of Glyceraldehyde referred to as the


Enantiomers of Glyceraldehyde ?
Ans :
The stereoisomers of glyceraldehyde are mirror images of each other and
are non superimposable images. Hence they are referred to as the
Enantiomers of Glyceraldehyde.

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Q 28. What does the ( + ) and ( - ) notation in the name of the stereoisomer
indicate ?
Ans :
(+) … indicates that the compound is dextro rotatory.

(-) … indicates that the compound is laevo rotatory.

Q 29 . What are Chiral and Achiral objects ?


Ans :
Objects which are non-superimposable on their mirror images → chiral
objects.
Chiral objects do not have a plane of symmetry.
Objects which are superimposable on their mirror images → achiral objects .
Achiral objects will have a plane of symmetry.

Q 30 . How is Glucose synthesised in the lab ?


Ans :
1. From Sucrose ( cane sugar ) : { from disaccharides }
Step 1: Sucrose is boiled with dil HCl or dil H2SO4 .
This hydrolyses Sucrose into Glucose and Fructose.
Step 2 : On cooling alcohol is added in order to crystallise the Glucose from
solution.
Fructose remains in the solution

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2. From Starch : { from polysaccharides }
Acidic hydrolysis of starch at nearly 400 K under pressure .

Q 31. What is Dextrose ?


Ans:
Dextrose is a naturally occurring form of glucose seen in food products.
It has a high glycemic index.
Dextrose is biochemically similar to D – glucose.

Q 32. Evidences to show the Open chain structure of Glucose.

( a ) Evidence to show that the 6 carbon atoms of glucose are in a straight


chain.
Ans : On strong heating with HI , glucose forms n-hexane.

(b) Evidence to show that Glucose has a carbonyl group.


Ans:
(1) Glucose reacts with Hydroxylamine to give oximes. { Glucose Oxime }

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(2) Glucose reacts with HCN to form cyanohydrins.
{Glucose cyanohydrin }

(c) Evidence to show that the carbonyl group in Glucose exists as an


aldehyde.
Ans: Glucose is oxidised by Bromine water to form Gluconic acid.

(d) Evidence to show the presence of 5 OH groups on different carbon


atoms.
Ans: Glucose reacts with 5 molecules of acetic anhydride to form Glucose
pentaacetate.

(e) Evidence to show the presence of a Primary alcoholic group.


Ans: Glucose is oxidised by strong oxidising agents like HNO3 to give
Saccharic acid.

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Q 33. What are the pieces of evidence against the Open chain structure of
Glucose ?
Ans :

(a) Though glucose has a – CHO group , it doesn’t give Schiff’s Test

(b) Though glucose has a -CHO group , it doesn’t form a bisulphite addition
compound with NaHSO3

(c) Though glucose has a -CHO group , it doesn’t give the 2 , 4 – DNP test

(d) The glucose pentaacetate doesn’t react with Hydroxyl amine.


Hence the -CHO group is not free.

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