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 CHEMISTRY
CHAPTER 8: ORGANIC CHEMISTRY SOME BASICPRINCIPLES AND
TECHNIQUES
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ORGANIC CHEMISTRY SOME BASICPRINCIPLES AND

TECHNIQUES

Introduction

In this chapter, we shall discuss some basic principles and techniques of analysis needed for
understanding the formation and properties of organic compounds. Organic compounds are
essential for existence and maintenance of life on earth. These include complex molecules like
(DNA) which carry genetic information and proteins which is building blocks of life. Organic
compounds also play an important role in material used in daily life such as cloths, fuel, dyes,
and medicines etc.

Structural Representations of Organic Compounds

Structural Formulas

The Lewis structures can be simplified by representing the two electron covalent bonds by a
dash (–). In this representation, a single bond is represented by a single dash (–), a double bond
by a double dash (=) and a triple bond by a triple dash (≡). The lone pair on an atom may or may
not be shown. This representation is called structural formula.

Condensed Formulas

In this formula, the arrangement of atoms are shown but the bonds between may be omitted
and the number of identical groups attached to an atom are indicated by a subscript.

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Condensed Formulas

In this representation, the carbon and hydrogen atoms are not shown and the lines between
carbon-carbon bonds are shown in a zig-zag manner.

In cyclic compounds, the bond-line formulas may be given as follows:

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Three-dimensional representation of organic molecules

The three-dimensional (3-D) structure of organic molecules can be represented on paper by

using certain conventions. In these formulae, the thick solid (or heavy) line or the solid wedge
indicates a bond lying above the plane of the paper and projecting towards the observer while
a dashed wedge is used to represent a bond lying below the plane of the paper and projecting
away from the observer.

Classification of Organic Compounds

On the basis of their structures, organic compounds are broadly classified as follows:

Open Chain Compounds

These compounds contain open chains of carbon atoms in their molecules. The carbon chains
may be either straight chains or branched chains. They are also called aliphatic compounds.

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Closed Chain or Ring Compounds

These compounds contain chains or rings of atoms in their molecules.
Alicyclic Compounds: These compounds contain a ring of three or more carbon atoms in them.
They resemble aliphatic compounds in many of their properties.

Aromatic Compounds: These have a cyclic system containing at last one benzene ring. The
parent member of the family is called benzene. Benzene has a homocyclic hexagonal ring of six
carbon atoms with three double bonds in the alternate positions.

Heterocyclic Compounds: In these compounds, the ring contains one or more atoms of either
nitrogen, oxygen or sulphur in addition to carbon atoms. The atom other than carbon (such as
N, O, S) present in the ring is called hetero atoms.

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Functional Groups: An atom or group of atoms which largely determines the properties of the
organic compounds particularly the chemical properties.

Homologous Series: Homologous series may be defined as “a series of similarly constituted

compounds in which the members possess the same functional group and have similar
chemical characteristics”. The two consecutive members differ in their molecular formula by –
CH2– group.
1. CH3OH - Methyl alcohol
2. C2H5OH - Ethyl alcohol
3. C3H7OH - Propyl alcohol
4. C4H9OH - Butyl alcohol
5. C5H11OH - Pentyl alcohol
6. C6H13OH - Hexyl alcohol

Nomenclature of Organic Compounds

The term ‘nomenclature’ means the system of naming of organic compounds. There are two
systems of nomenclature:

1. Trivial or Common System

In this nomenclature, the names of organic compounds were assigned based on their source
of origin or certain properties. For instance, citric acid got its name from the source (citrus
fruits) from which it was first isolated. Formic acid was named so as it was first obtained from
red ant. In Latin ant word is formica.

2. IUPAC System of Nomenclature

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A systematic method of naming has been developed and is known as the IUPAC (International
Union of Pure and Applied Chemistry) system of nomenclature. In this systematic
nomenclature, the names are correlated with the structure such that the reader or listener
can deduce the structure from the name.

Free Radicals
Free Radical
A free radical may be defined as an atom or a group having an odd or unpaired
electron.These are generally produced by homolytic cleavage of a covalent bond.

Classification of Free Radicals

Free radicals are also classified as primary (1°), secondary (2°) and tertiary (3°)
according as the carbon carrying the unpaired electron is primary, secondary and
tertiary.

Stability of Free Radicals

The order of stability of free radicals is the same as that of carbocations i.e. 3° >2° >1°

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This order of stability can be explained on the basis of hyperconjugation.

Greater the number of alkyl groups attached to the carbon atom carrying the odd
electrons, greater is the delocalization of the odd electrons and hence more stable is
the alkyl free radical.

Stability of free radical

Allyl and benzyl free radicals are stabilized by resonance.

Greater the number of phenyl groups more stable is the free radical.

Free radicals are also very short-lived highly reactive chemical species because of the
strong tendency of the carbon atom carrying the odd electron to acquire one more
electron to complete its octet.
Orbital structure of Free Radicals

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Alkyl free radicals are planar chemical species.In free radicals, the unhybridized p-
orbital contains the odd electron.
Like carbanions , free radicals can also assume pyramidal shape since the energy
difference between planar and pyramidal shape is not much.

Stereoisomerism
Isomers which have same structural formula but have different relative arrangement or
atoms or groups in space are called stereoisomers and the phenomenon is called
stereoisomerism.

cis-trans isomerism is an example of stereoisomerism.

cis-trans isomers
Due to π-bonding between the two carbon atoms, the rotation around carbon-carbon
double bond is prohibited and hence the geometry of the atoms or groups attached to
the carbon atoms gets fixed in space.
Stereoisomerism is also called geometrical isomerism.

Steric Hindrance

If two non-bonded atoms or groups in an organic molecule are held together at a

distance equal to or less than the sum of their van der waal radii, then they repel each
other due to spatial crowding.This repulsion is referred to as steric hindrance or steric
strain or van der waal strains.
Molecules which possess steric strain are relatively less stable as compared to those
having no steric strain.

For Example: Cis-but-2-ene has steric hindrance and hence is less stable as compared

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to trans-but-2-ene which has no steric hindrance.

As the size of the atoms around a bulky atom increases, the steric hindrance increases
accordingly.

Summary-
1. Condensed Structural Formula: The structural formulae obtained by omitting some or all
the covalent bonds and by indicating the number of identical groups attached to an atom
by subscript is called condensed structural formula.
2. Bond-line Structural Formula: In this formula of organic compounds, carbon and hydrogen
atoms are not shown and line representing C –C bonds and drawn in zig-zag fashion. The
only atoms specifically written are those that are neither nor hydrogen bonded to carbon.
3. Cyclic Compounds: These are compounds in which carbon atoms are joined in rings i.e.,
they are closed chain compounds.
4. Aromatic Compounds: Benzene and its derivatives are called aromatic compounds.
5. Functional group: Functional group is an atom or group of atoms or reactive part of the
compound which determines physical and chemical properties of compounds.
6. Homologous Series: Homologous series is a series of compounds which has same
functional group same general formula and show gradation in physical and chemical
properties of compounds.
7. Isomerism: The phenomenon of existence of two or more compounds possessing the same
formula but different structural formula and different physical and chemical properties are
called isomerism.
8. Structural Isomerism: Compounds having the same molecular formula but different
structures are classified as structural isomers. Chain Isomerism: The isomers, which differ
in carbon atom chain, are called chain isomers and this phenomenon is called chain
isomerisms.
9. Position Isomerism: The isomers, which differ in position of substituent or functional
groups are called position isomers and this phenomenon is called position isomerism.
10.Functional Isomerism: Those isomers, which differ in functional groups are called
functional isomers and this phenomenon is called functional isomerism.
11.Metamerism: Those isomers, which differ in alkyl group attached with the di or tri valent
atom of functional group. These are called metamers and this phenomenon is called
metamerism.
12.Stereoisomerism: Those compounds that have the same composition and sequence of
covalent bond but differ in relative positions of their atoms or groups in space.

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13.Free Radical: An atom or group of atoms containing odd unpaired electrons in excited
state is known as free radical.

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Important Questions

Multiple Choice questions-

Question 1. Which among the following statement is not true?
(a) In liquid, particles are less regularly arranged and are free to move
(b) Boiling involves breaking up of group of molecules in liquid
(c) Boiling involves separation of oppositely charged ions
(d) Thermal energy of particles overcome cohesive forces that hold them
Question 2. Identify the chiral molecule among the following:
(a) Isopropyl alcohol
(b) 2-pentanol
(c) 1-bromo 3-butene
(d) Isobutyl alcohol
Question 3. Which element is estimated by Carius method?
(a) Carbon
(b) Hydrogen
(c) Halogen
(d) Nitrogen
Question 4. A solution of (+) – 2 – chloro – 2 – phenylethane in toluene racemises slowly in the
presence of small amounts of SbCl5 due to the formation of
(a) Carbanion
(b) Carbene
(c) Free radical
(d) Carbocation
Question 5. Which of the following acids has the smallest dissociation constant?
(a) CH3CHFCOOH
(b) FCH2CH2COOH
(c) BrCH2CH2COOH
(d) CH3CHBrCOOH
Question 6. What is the correct IUPAC name of?

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(a) 4-methoxy-2-nitrobenzaldehyde
(b) 4-formyl-3-nitro anisole
(c) 4-methoxy-6-nitrobenzaldehyde
(d) 2-formyl-5-methoxy nitrobenzene
Question 7. 0.5 g of hydrocarbon gave 0.9 g water on combustion. The percentage of carbon in
hydrocarbon is
(a) 75.8
(b) 80.0
(c) 56.6
(d) 28.6
Question 8. 0.92 g of an organic compound was analysed by combustion method. The mass of
the U- tube increased by 1.08 g. What is the percentage of hydrogen in the compound?
(a) 13.04%
(b) 52.17%
(c) 65.21%
(d) 11.30%
Question 9. What is the state of hybridisation of carbon in carbanion?
(a) sp
(b) sp²
(c) sp³
(d) sp²d.
Question 10. An organic compound contains C = 38.8 H = 16 and N = 45.2. Empirical formula of
the compound is
(a) CH3NH2
(b) CH3CN
(c) C2H5CN
(d) CH2(NH)2

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Question 11. 59 g of an amide obtained from a carboxylic acid, RCOOH, liberated 17 g of

ammonia upon heating with alkali. The acid is
(a) Formic Acid
(b) Acetic Acid
(c) Propionic Acid
(d) Benzoic Acid
Question 12. The displacement of electrons in a multiple bond in the presence of attacking
reagent is called
(a) Inductive effect
(b) Electrometric effect
(c) Resonance
(d) Hyper conjugation
Question 13. The molecular formula C5H12 contains how many isomeric alkanes?
(a) 1
(b) 2
(c) 3
(d) 4
Question 14. If two compounds have the same empirical formula but different molecular
formula, they must have
(a) Different percentage composition
(b) Different molecular weight
(c) Same viscosity
(d) Same vapour density
Question 15. Inductive effect involves
(a) Displacement of σ electrons
(b) Delocalization of π electrons
(c) delocalization of σ-electrons
(d) Displacement of π-electrons

Very Short:
1. What type, of hybridisation, is involved in

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(i) planar and

(ii) linear molecules?
2. Arrange the following in increasing order of C – C bond strength:
C2H6, C2H4C2H2
3. Arrange the following in decreasing order of C — C bond length:
4. What is the type of hybridisation of C atoms in benzene?
5. What are isomers?
6. Select electrophiles out of the following:
H+ Na+, Cl–, C2HSOH, AlCl3, SO3, CN–, CH3CH2+,: CCl2, R-X.
7. Select nucleophiles from the following.
BF3 NH3 OH–, R-X, C2H5OH, H3O+, NO2, CN–.
8. Give the I.U.P.A.C. names of the following compounds

(v) (CH3)4C
(vi) (CH3)2CHCOOH.
9. What is a functional group?
10. Arrange the following in increasing order of-I effect.
(i) -NO2, -COOH, -F, -CN, – I.

Short Questions:
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1. Expand each of the following bond-line formulae to show all the atoms including carbon
and hydrogen.

(d)
2. For each of the following compounds, write a more condensed and also their bond line
formulae.

3. What is the type of hybridisation of each carbon in the following compounds?

(a) CH3Cl
(b) (CH3)2CO
(c) CH3CN

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(d) HCONH2
(e) CH3CH = CHCN.
4. What is the shape of the following molecules:
(a) H2C = O
(b) CH3F
(c) H-C ≡ N?
5. Give the I.U.P. A.C. names of the following compounds:

(ii) CH3 – CH = CH COOH

(iii) (CH3)2C = CHCOCH3

(vi) CH2 = CH – CN.

6. Write the I.U.P.A.C. names of

Long Questions:
1. Explain the principle of steam distillation.

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2. Dehydrobromination of compounds (A) and (B) yield the same alkene (c) Alkene (c) Can
regenerate (A) and (B) by the addition of HBr in the presence and absence of peroxide
respectively. Hydrolysis of A and B give isomeric products (D) and (E) respectively. 1, 1-
Diphenyl ethane is obtained on the reaction of (C) of benzene in the presence of H+ ions.
Give structures of A to E with reactions.
3. What are reaction intermediates? How are they generated by bond fission?
4. 0.395 g of an organic compound by various method for the estimation of sulphur gave
0.582g of BaS04. Calculate the percentage of Sulphur.
5. 0.15g of an organic compound gave 0.12g of AgBr by carius method. Find the percentage of
bromine in the compound.

Assertion Reason Questions:

1. In the following questions, a statement of Assertion (A) followed by a statement of Reason
(R) is given. Choose the correct option out of the choices given below each question.

Assertion (A) : Simple distillation can help in separating a mixture of

propan-1-ol (boiling point 97°C) and propanone (boiling point 56°C).
Reason (R) : Liquids with a difference of more than 20°C in their boiling
points can be separated by simple distillation.
(i) Both A and R are correct and R is the correct explanation of A.
(ii) Both A and R are correct but R is not the correct explanation of A.
(iii) Both A and R are not correct.
(iv) A is not correct but R is correct.

2. In the following questions, a statement of Assertion (A) followed by a statement of Reason

(R) is given. Choose the correct option out of the choices given below each question.

Assertion (A) : Energy of resonance hybrid is equal to the average of energies

of all canonical forms.
Reason (R) : Resonance hybrid cannot be presented by a single structure.
(i) Both A and R are correct and R is the correct explanation of A.
(ii) Both A and R are correct but R is not the correct explanation of A.
(iii) Both A and R are not correct.
(iv) A is not correct but R is correct.

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Case Study Based Question:

1. Read the passage given below and answer the following questions:
The electron displacements due to the influence of an atom or a substituent group
present in the molecule cause permanent polarisation of the bond (called electronic effect),
e.g.

In above example, polar C—F bond induce polarity in the adjacent bonds. Such polarisation
of adjacent σ- bond is referred to as the inductive effect. This effect decreases rapidly as the
number of intervening bonds increases. The resonance effect is defined as the polarity
produced in the molecule by the interaction of two π-bonds or in conjugated system.
When the group or atom release electron density then electron density of conjugated
system increases while the group or atom attract/withdraw electron density then electron
density of conjugated system decreases.
(1) In which molecule dipole moment is the maximum?

(2) In which benzene ring electron density is maximum?

(3) Which of the following system show abnormal behaviour in their properties (like-
stability, polarity ... etc.) ?

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(4) The permanent displacement of electron through a chain involving only σ-bonds is called
(a) Inductive effect
(b) Hyperconjugation effect
(c) Electrometric effect
(d) Mesmeric effect
2. Read the following passage and answer the question accordingly.
An intermediate is a molecular entity, that is formed from the reactants and reacts further
to give the directly observed products of a chemical reaction. Most chemical reactions are
stepwise, that is they take more than one elementary step to complete. An intermediate is
the reaction product of each of these steps, except for the last one, which forms the final
very isolated. Also, owing to the short lifetime, they do not remain in the product mixture.
In certain cases, they are separated and stored. For example matrix isolation and low
temperature. Matrix isolation is a technique that is used experimentally in physics and
chemistry that includes a material that has been trapped with in an unreactive material.
Host matrix generally comprises guest particles that are generally embedded. Guest
particles can be molecules, atoms and ions. The guest is isolated within the host matrix.

(1) Relative stabilities of the following carbocations will be in the order

(a) C > B > A

(b) C < B < A
(c) B > C > A
(d) C > A > B
(2) CH3 CH2 Cl undergoes homolytic fission, produces.

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(3) The shape of carbocation is:

(a) square planar
(b) trigonal planar
(c) octahedral
(d) trigonal pyramidal
(4) Compare stability of free radicals.

(a) II > I > III > IV

(b) II > I > IV > III
(c) I > II > III > IV
(d) IV > III > I > II

Answer Key:
MCQ
1. (c) Boiling involves separation of oppositely charged ions

2. (d) Isobutyl alcohol

3. (c) Halogen

4. (d) Carbocation

5. (c) BrCH2CH2COOH

6. (a) 4-methoxy-2-nitrobenzaldehyde

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7. (b) 80.0

8. (a) 13.04%

9. (c) sp³

10.(a) CH3NH2

11.(b) Acetic Acid

12.(b) Electrometric effect

13.(c) 3

14.(b) Different molecular weight

15.(a) Displacement of σ electrons

Very Short Answer:

1. (i) sp2

(ii) sp.

2. C2H6 < C2H4 < C2H2.

3. C2H6 > C2H4 > C2H2.

4. It is an sp2 type of hybridisation.

5. Compounds having the same molecular formula, but different physical and chemical
properties are called isomers.

6. H+, Na+, A1Cl3, SO3, CH3CH2+,: CCl2, R-X.

7. NH3, OH, C2H5OH, CN

8. (i) 2-Bromo-4 – methyl pent-3- one
(ii) 4-Methyl-2-nitro pent – 3 – one
(iii) 2 – Ethoxy – 4 – methoxypent – 3 – one
(iv) 2-Bromo-4-nitro pent-3-one
(v) 2, 2-Dimethylpropane

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(vi) 2-Methyl propanoic acid.

9. The atom or group of atoms present in a molecule that determines its chemical properties is
called the functional group.
10. -I < -F < -COOH < -CN <NO2.

Short Answer:
Ans: 1.

(a)

(b)

(c)

(d)

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Ans: 2. (a) Condensed formulae are

(CH3)2CH CH2 OH

(b) CH3(CH2)5 CHBr CH2 CHO

(c) HO(CH2)3 CH(CH3) CH(CH3)2

(d) HOCH(CN)2

Ans: 3.

(a)

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(b)

(c)

(d)

(d)

Ans: 4. (a) In H2C = O; C is sp2 hybridised, hence its shape is H trigonal planar

(b) In CH3F -F; C is sp3 hybridized

∴ it is tetrahedral

(c) In H-C ≡ N; C is sp-hybridized, hence HCN is linear

H—C ≡ N.

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Ans: 5. (i) 2-Ethylprop-2-en-l-ol

(ii) But-2-en-l-oic acid

(iii) 4-Methylpent-3-en-2-one

(iv) 3-Chloropropanal

(v) 3-Methylbutane-l-al

(vi) Prop-2-en-1-nitrile.

Ans: 6. (i) 3-Ethyl-4-methylhept-5-en-2-one

(ii) 2-Ethyl-3-methylpent-2-en-1 -one.

Long Answer:
Ans: 1. Steam distillation: The process of steam distillation is employed in the purification of
substance from non-volatile impurities provided the substance itself is volatile in steam and
insoluble in water.

This method is based on the facts that

1. A liquid boils at a temperature when its vapour pressure becomes equal to the
atmospheric pressure.

2. The vapour pressure of a mixture of two immiscible liquids is equal to the sum of the
vapour pressures of the individual liquids.

In the actual process, steam is continuously passed through the impure organic liquid. Steam
heats the liquid and it gets practically condensed to water. After some time, mixture of the liquid
and water begins to boil, because the vapour pressure of the mixture becomes equal to the
atmospheric pressure.

Obviously, this happens at a temperature that is lower than the boiling point of the substance or
that of water. Thus an organic compound boils below its boiling points and chances of
decomposition avoided. For example, a mixture of aniline (b.p 453 K) with decomposition and
water (b.p. 373 K) under normal atmospheric pressure boils at 371K. At this temperature the

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Steam Distillation

water boils at 371 K. At this temperature, the vapour pressure of water is 717 mm and that of
aniline is 43 mm and therefore the total pressure is equal, to 760 mm. Thus in steam
distillation, the liquid gets distilled at a temperature lower than its boiling point and chances of
decomposition avoided. The proportion of water and liquid in the mixture that distils over is
given by the relation.

where w1 and w2 stand for the masses of water and liquid that distils over. P1 and P2 are vapour
pressure of water and of liquid at the distillation temperature and M is the molecular mass of
the liquid.

Ans: 2. Alkene (C) on reaction with benzene in the presence of H+ ions give 1, 1-Diphenyl ethane.
Therefore, C must be styrene as depicted below

Now dehydrobromination of A and B give the same alkene C, i.e.,

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styrene.
∴ A and B must be isomeric alkyl bromide

A and B can be obtained by the addition of HBr in the presence and absence of peroxide to
styrene.

Hydrolysis of A and B give isomeric alcohols (D) & (E) as

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Ans: 3. The species which are generated as a result of bond fission are called reaction
intermediates. The important reaction intermediates are:
1. Free Radicals: A free radical may be defined as an atom or group of atoms having an impaired
electron. These are obtained as a result of homolytic fission of covalent bonds.

These free radicals are neutral particles, extremely transient, (short-lived) and highly reactive.
They get consumed as soon as they are formed. They pair up their electron with another
electron from wherever it is available. They occur only as a reaction intermediate. Their
presence is felt in reactions, but cannot be isolated in a free state. For example dissociation of
Cl2 gas in the presence of Ultraviolet light produces free radicals.

The alkyl free radicals are obtained when free radical: Cl reacts with alkanes.

Free radical may be primary, secondary, tertiary depending upon whether, one, two or three
carbon atom attached to the carbon atoms carrying the odd electron.

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The stability is CH3 < 1° < 2° < 3°.

2. Carbocation or carbonium ion: It is defined as a group of atoms that contain positively charged
carbon having only six electrons. It is obtained by heterolytic fission of a covalent bond
involving a carbon atom.

They are also classified as primary, secondary and tertiary depending upon whether one, two
or three carbon atoms are attached to the carbon bearing the positive charge as:

Thus, the order of stability if CH3+ < 1° < 2° < 3°.

3. Carbanion: A carbanion may be defined as a species containing a carbon atom carrying a

negative charge. These are generated by the atom in which the atom linked to carbon goes
without the bonding electrons. As a result of this carbon acquires a negative charge. For
example, the removal of hydrogen of methyl part of acetaldehyde molecule as H+ ion leaving
both the electron on carbon.

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They are also very reactive species. They are also classified as primary, secondary and tertiary
depending upon whether one, two or three carbon atoms are attached to the carbon atom
bearing negative
charge.

The order of stability is the reverse of free radicals and carbocations

CH3 – > 1° > 2° > 3°.

(iv) Carbenes: The carbenes are reactive neutral species in which carbon atom has six
electrons in the valency shell out of which two are shared. The simplest carbene is methylene
(CH2). It is formed when diazomethane is decomposed by the action of light.

It is very reactive. It reacts with alkenes by adding to the double bond forming cyclopropane.

Ans: 4. Mass of BaSO4 = 0.582 g

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BaSO4 = S

233 = 32

233g of BaSO4 contain sulphur = 32g

0. 582 g of BaSO4 contains sulphur

Ans: 5. Mass of AgBr formed = 0.12g

188 g of AgBr contains bromine = 80g.

Therefore, 0.12g of AgBr will contain bromine

80 × 0.12
= = 0.051 g
188

0.051
Percentage of bromine = × 100 = 34%
0.15

Assertion Reason Answer:

1. (i) Both A and R are correct and R is the correct explanation of A.

2. (iv) A is not correct but R is correct.

Case Study Answer:

1. Answer:

(1) (b) CH3 CH2 CH2 — NO2

(32)
 ORGANIC CHEMISTRY – SOME BASIC PRINCIPLES & TECHNIQUES
12

(2)

(3)

(4) (a) Inductive effect

2. Answer:

(1) (a) C > B > A

(2)

(3) (b) trigonal planar

(4) (b) II > I > IV > III

(33)
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