NOTE

C H E M I S T R Y

GENERAL ORGANIC CHEMISTRY

EXPLORING THE WORLD OF CARBON
AND ITS COMPOUNDS

What you will learn

• Organic compounds • Representation of organic molecules

• Vital force theory • Classification of organic compounds
• Bonding in organic compounds • Hydrocarbons
• Why are there countless organic • Functional groups
compounds? • Homologous series

BOARDS
Organic Compounds

We are surrounded by an abundance of organic compounds. Few examples of organic compounds

present around us in various forms are as follows:

Wood
Human
skin Food

Detergent Plastic

Soap
Fig. 1: Examples of organic compounds

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Organic compounds are also found in medicines. Few of them are given as follows:
Paracetamol

Cephalexin Aspirin

Medicines

Ibuprofen Hydroxy
chloroquine
Remdesivir
Fig. 2: Organic compounds in medicines

History of organic compounds

1. Berzelius vital force theory

Berzelius was a Swedish chemist. He proposed that living beings have a vital force in them. The
compounds or substances derived from living systems are known as organic compounds.
These substances cannot be synthesised in the laboratory.
However, the compounds or substances derived from non-living systems are known as
inorganic compounds. Inorganic compounds or substances do not have vital forces and can be
synthesised in laboratory.
2. Wöhler theory
In 1828, Wöhler synthesised an organic compound urea from an inorganic compound of
ammonium cyanate in the laboratory, proving the earlier vital force theory wrong. Thus, urea
was the first organic molecule to be synthesised.
O
_
NH4+CNO C
H H
N N
H H
Ammonium Urea
cyanate
Synthesis of urea from ammonium cyanate (Wöhler theory)

Definition of organic compounds

Organic compounds are compounds of carbon and hydrogen and their derivatives. The study of
these compounds is done in a separate branch of chemistry known as organic chemistry.

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Example: The wood is made up

of cellulose, which is an organic
compound. It contributes to the Cellulose
fibre properties. Fibres

Table
Fig. 3: Cellulose in wood

Why are there countless organic compounds around us?

It is due to the properties of carbon that forms numerous compounds.

• Tetravalency of carbon • Catenation • Tendency to form bonds
with other non-metals
1. Tetravalency of carbon
Tetravalency means the tendency to form four bonds. Each carbon atom can form four bonds.
Examples:
H Cl

H___ C___ H Cl ___ C___ Cl

H Cl
Methane (CH4) Tetrachloromethane (CCl4)
In methane, carbon forms four bonds with the hydrogens, while in tetrachloromethane, carbon
forms four bonds with the halogen (here, Cl).
2. Catenation
The self-linking property between atoms of the same element is known as catenation. Carbon
shows the property of catenation.
H

C C C C C H C H
C C
C C C C C C C
C C
C C C C C H C H

H
Fig. 4: Illustration of catenation property of carbon

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It can combine with other carbon atoms by single, double, and triple bonds.

C C C C

C C C C C C C

Single bond Double bond Triple bond

C C

Fig. 5: Types of covalent bonds formed by carbon atom

On the other hand, when atoms like oxygen and nitrogen form bonds with themselves, they
are generally unstable.
For example: H2O2 molecule (having peroxy linkage, H−O−O−H) is unstable. Similarly, N3− (azide
ion) is unstable. So, these atoms do not possess catenation property.
The number of bonds that the carbon can form with other atoms depends on the tendency of
the other atom to form multiple bonds.
Example:
(i) It can form single, double, and triple bonds with nitrogen atom as follows:
Single bond: C−N Double bond: C=N Triple bond: C≡N
(ii) It can form a single bond with halogens C−X, here X is F, Cl, Br, and I.
(iii) It can form single and double bonds with oxygen as follows:
Single bond: C−O Double bond: C=O
3. Tendency to form bonds with other non-metals
In organic molecules, atoms other than carbon and hydrogen can also be present.
For example: N, O, X (X is F, Cl, Br, or I), S, P, etc.

BOARDS
Bonding in Organic Compounds

Type of covalent bond

Sigma (𝛔) Pi (𝛑)

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Note

Sigma bond is stronger than pi bond.

• Number of pi bonds of carbon atoms and hybridisation of carbon

Type of covalent bond Number of pi bonds Hybridisation of carbon

Single 0 sp3

Double 1 sp2

Triple 2 sp

Table 1: Hybridisation based on the types of covalent bond

Example: In carbon dioxide molecule, O=C=O, the central carbon atom

has two pi bonds, one with each oxygen atom. Thus, the
sp
hybridisation of the carbon atom is sp. O C O

Based on the number of sigma and pi bonds and hybridisation

(a) Calculate the number of sigma (σ) and pi (π) bonds in

a compound. H3C __ CH CH__ CH2__ C CH
(b) Determine the hybridisation of each carbon atom in a 1 2 3 4 5 6
molecule.

Solution

(a) Number of sigma bonds = 13

Number of pi bonds = 3 (One pi bond between carbon 2 and 3, and other two pi bonds between
carbon 5 and 6)
(b) Hybridisation of C (1) = sp3 (As it does not form any pi bond)
Hybridisation of C (2) = sp2 (As it forms one pi bond)
Hybridisation of C (3) = sp2 (As it forms one pi bond)
Hybridisation of C (4) = sp3 (As it does not form any pi bond)
Hybridisation of C (5) = sp (As it forms two pi bonds)
Hybridisation of C (6) = sp (As it forms two pi bonds)
sp3 sp2 sp2 sp3 sp sp
H3C __ CH CH__ CH2__ C CH
1 2 3 4 5 6

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BOARDS
Representation of Organic Molecules

Molecular formula Complete formula

Structural representation Condensed formula

Bond-line formula

(1) Molecular formula: It shows the exact number of different types of atoms present in a molecule
or a compound. Examples: C2H6, C4H10, CH4, C6H12O6, etc.
(2) Structural representation
(a) Complete/Expanded formula
A single dash (–) represents a single bond, a double dash (=) represents a double bond, and
a triple dash (≡) represents a triple bond. The lone pairs of electrons on heteroatoms (for
example, oxygen, nitrogen, sulphur, halogen, etc.) may or may not be shown.

H H H H H

H___ C ___ C ___ H H___ C ___ C ___ C ___ H

H H H H H
C2H6 C3H8

H H
H H H
C C H___ C ___ C C
H H H
H
C2H4 C3H6

H___ C C ___ C ___ H

H
C3H4
Expanded formula of organic compounds
(b) Condensed formula
It omits some or all of the dashes representing the covalent bonds. It indicates the number
of identical groups attached to an atom by a subscript.

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Examples:
1. CH3−CH3
2. CH3−CH2−CH2−CH3 or CH3CH2CH2CH3 or CH3(CH2)2CH3

(c) Bond-line formula

It represents organic compounds, where hydrogen atoms are not shown and carbon is
represented by corners. The lines representing C-C bonds are drawn in a zig-zag pattern.
Atoms other than carbon and hydrogens attached to carbons, are specifically written.
For example: Oxygen, chlorine, nitrogen, etc.
OH

Cl H2N
Pentane Butanol 1-Chloro-3-methylbutane 1-Methyl propanamine

The structural representations for the molecular formula, C4H10 are given as follows:
H H H H

H___ C ___ C ___ C ___ C ___ H H3C___ CH2___ CH2___ CH3

H H H H
Expanded structure Condensed structure Bond-line structure
Heteroatoms: Atoms other than carbon and hydrogen in organic compounds are known as
heteroatoms.

Based on the representation of molecules

H H
H H
H H
Determine the bond-line formula for the given molecule.
H H
O H
H

Solution

The bond-line formula of the compound can be drawn as shown:

The C−H bonds are not shown specifically. However, the hydrogen
attached to the heteroatom is shown (here, OH). OH

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BOARDS
3D Representation of Organic Molecules

The 3D structure of a molecule is shown using dashes, wedges, and straight lines. Straight lines
represent bonds in the plane, whereas wedge and dash bonds represent bonds towards and away
from the observer, respectively.
H H
Dash bond

sp3 C Represented using

C H H
H dash bond
H
H
Wedge
H Represented using
bond
wedge bond
Fig. 6: 3D representation of tetrahedral molecule (CH4)

BOARDS
Classification of Organic Compounds

Classification of organic compounds

Cyclic Acyclic

Alicyclic Aromatic Straight-chain Branched-chain

Homocyclic Heterocyclic

Benzenoid Non-benzenoid Heterocyclic

• Cyclic compounds
These are the compounds in which the carbon atoms are linked to each other or to the atoms of
other elements in such a manner that the molecule has a closed-chain, cyclic, or ring structure.
Both alicyclic and aromatic compounds are considered as cyclic compounds.

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Examples: Cyclohexane, benzene, pyridine, etc.

:
(a) (b) (c)

1. Alicyclic: The molecules that do not have a special stability

of pi bonds are known as alicyclic compounds.
Example: Cyclopropane
Cyclopropane
These compounds are further classified into homocyclic and
heterocyclic molecules.

• Homocyclic: Here, all the atoms that form the ring are
only carbons.
Example: Cyclohexane
Cyclohexane

S
• Heterocyclic: Here, the cyclic ring involves carbons as
well as other heteroatoms like N, O, S, etc.

Tetrahydrothiophene
2. Aromatic: Aromatic compounds are those cyclic compounds that have alternate double and
single bonds (follows Huckel rule and conditions of aromaticity), which have extra or
special stability.
Example: Benzene
It is further classified into the following:

• Benzenoid compounds: It involves only benzene rings.

Examples: Naphthalene, anthracene, etc.
Naphthalene
—
• Non-benzenoid compounds: It does not involve any
benzene ring.
_
Example: Cyclopentadienyl anion (C5H5 ).

Cyclopentadienyl anion

• Aromatic heterocyclic: Here, the ring contains carbons

as well as the heteroatoms
like N, S, O, etc. However, these
:

N
compounds are still aromatic
(follow conditions of aromaticity). H
Example: Pyrrole Pyrrole

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• Acyclic compounds
These are the compounds in which the carbon atoms are
linked to each other in such a manner that the molecule has
an open-chain structure.
Example: 2-Methyl propane 2-Methyl propane

H H H

1. Straight-chain: These are the compounds that have H___ C ___ C ___ C ___ H
all the carbon atoms connected to
each other in a single chain.
H H H
Propane

CH3

2. Branched-chain: The compounds that have one or H3C___ C___ CH3

more than one branch are known
as branched-chain compounds.
CH3
Neopentane

Based on the classification of organic compounds

Which of the following structures is homocyclic and aromatic?

(a) (b) (c) (d) None of these

:

Solution

Homocyclic compounds are those compounds that do not have any heteroatoms.
Also, aromatic compounds are those compounds that have alternate double and single bonds, and
there is extra stability because they follow the conditions of aromaticity
Therefore, the correct answer is option (b).

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Based on the classification of organic compounds

Which of the following is not an alicyclic compound?

(a) (b) (c) (d)

Solution

The molecules that do not have a special stability of pi bonds (do not have alternate double and
single bonds and do not follow conditions of aromaticity) are known as alicyclic compounds. They
can be homocyclic or heterocyclic. Options (a), (b), and (c) represent the alicyclic molecules.
Thus, the correct answer is option (d).

Based on the condensed formula

Which of the following is the condensed formula for the given bond-line OH
formula?
(a) HOCH2CH2NH2 (b) HOCH2CH2CH2NH2
(c) HOCH3CH2NH2 (d) None of these H2N

Solution

There are only two carbon atoms in the molecule. Also, we know that carbon is tetravalent, i.e., it
forms four bonds.
So, HOCH2CH2NH2 represents the condensed formula.
Therefore, the correct answer is option (a).

BOARDS
Hydrocarbons

The compounds that contain only carbon and hydrogen atoms are known as hydrocarbons.
Examples: CH3CH3, CH3CH2CH3

Hydrocarbons

Saturated Unsaturated

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Saturated hydrocarbons Unsaturated hydrocarbons

If each carbon atom joins four other atoms
(C or H), then it has no potential to form
more bonds. Therefore, it is saturated.
Examples: CH3-CH3, CH3-CH2-CH3, etc.
The carbon atoms forming double (C=C) or triple
(C≡C) bonds have the potential to bond with at
least one more monovalent atom. Therefore, they
are unsaturated. In other words, the compounds
that have double and triple bonds are known as
unsaturated hydrocarbons.
Examples: CH3-CH=CH2, CH3-C≡CH, etc.

Based on the saturated and unsaturated hydrocarbons

Identify the saturated and unsaturated compounds.

H H H H H H H H

H___ C ___ C C ___ C ___ H H___ C ___ C ___ C ___ H H___ C C ___ C ___ H

H H H H H H

(A) (B) (C)

Solution

Saturated hydrocarbons are those hydrocarbons that do not have any double or triple bonds.
Hence, the compound (B) is a saturated compound.
Unsaturated hydrocarbons are those compounds that have at least one double or triple bond.
Thus, the compounds (A) and (C) are unsaturated compounds.

BOARDS
Functional Group

An atom or a group of atoms joined in a specific manner, which is responsible for the characteristic
chemical and physical properties of the organic compound, is known as a functional group.
Example: CH3−CH2−CH2−CH2−COOH
The functional group −COOH is known as a carboxylic acid group.

BOARDS
Homologous Series

A series of similarly constituted compounds in which the members possess the same functional
group, have similar chemical characteristics, and have a regular gradation in their physical properties
is known as a homologous series.
The successive homologues differ by a −CH2 unit only.

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Homologues: The members of a homologous series are known as homologues.

Examples:
CH3−CH3, CH3− CH2− CH3, CH3− CH2− CH2− CH3, CH3− CH2− CH2− CH2− CH3, etc.

H H H H H H H H H
+CH2 +CH2
H C C H H C C C H H C C C C H

H H H H H H H H H

Ethane Propane Butane

Fig. 7: Homologous series (Alkanes)

Based on the hybridisation

Which of the following sequences shows the state CH3 CH3

of hybridisation of C2, C3, C5 and C6 of the given
hydrocarbon? H3C___ C ___ CH CH___ CH___ C CH
(a) sp3, sp2, sp2, and sp (b) sp, sp2, sp3, and sp2 7 6 5 4 3 2 1
(c) sp, sp2, sp2, and sp3 (d) sp, sp3, sp2, and sp3 CH3

Solution

CH3 CH3
Since C2 has two pi bonds, its hybridisation is sp.
sp sp
3 3
sp
2
sp
2
sp3 sp sp
Since C3 has no pi bond, its hybridisation is sp3.
H3C___ C ___ CH CH___ CH___ C CH
Since C5 has one pi bond, its hybridisation is sp2. 7 6 5 4 3 2 1
Since C6 has no pi bond, its hybridisation is sp3.
CH3
Therefore, the correct answer is option (d).

Based on the hybridisation

The structural formula of a compound is given. Find the H H H

types of hybridisation at the four carbons from left to right.
H ___ C ___ C C C
(a) sp2, sp2, sp2, sp3 (b) sp3, sp2, sp, sp2 1 2 3 4
(c) sp2, sp3, sp2, sp2 (d) sp3, sp2, sp2, sp2 H H

Solution

From left to right, the first carbon atom does not have any pi bond. So, its hybridisation is sp3.

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H H H
Since the second carbon atom has one pi bond, its hybridisation is sp .2
sp3 sp2 sp sp2
Since the third carbon atom has two pi bonds, its hybridisation is sp. H ___ C ___ C C C
Since the fourth carbon atom has one pi bond, its hybridisation is sp2. 1 2 3 4
H H
Therefore, the correct answer is option (b).

Based on the condensed formula

Which of the following is the condensed formula for the given structure?
(a) CH3CH=CH(CH2)4CH3 (b) CH3CH=CH(CH2)3CH3
(c) CH2=CH(CH2)4CH3 (d) None of these

Solution

The given compound contains seven carbon atoms. Also, the pi bond is formed between the
second and the third carbon atom.
Therefore, the correct answer is option (b).

Based on the classification of organic compounds

Which of the following structures is heterocyclic and alicyclic?

None of these
O
(A) (B) (C) (D)

Solution

Only compound (c) contains a heteroatom and it is alicyclic also.

Thus the correct answer is option (c).

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Based on the condensed and molecular formula

O
What is the molecular formula of the given compound?
(a) C12H8O2 (b) C11H6O2
(c) C10H6O2 (d) C10H8O2

Solution
H O
The molecular formula of the compound can be
obtained by counting the total number of carbon, H H
hydrogen, and oxygen atoms.
The molecular formula is C10H6O2. H H
Thus, the correct answer is option (c).
H O

Based on the hybridisation

How many sp2-sp2 sigma bonds are present in the given compound?
(a) 1 (b) 3
(c) 4 (d) 5

Solution
sp2
σ
sp2 sp2
There are a total of four sp2-sp2 sigma bonds.
σ σ
Thus, the correct answer is option (c). sp2
σ sp2
sp2

Based on the catenation property

Why is the property of catenation strongest in the carbon atom?

(a) Its ionisation potential is low. (b) Its electronegativity is low.
(c) The C−C bond energy is high. (d) Its atomic radius is small.

Solution

The carbon atoms have a high self-linking tendency (catenation) due to high C-C bond energy.
Thus, the correct answer is option (c).

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Based on the hybridisation

Which of the following hybridisations are involved in the bond between carbon atom (1) and carbon
atom (2) in the given compound?
(a) sp2 and sp2 (b) sp3 and sp 1 2 3
N C ___ CH CH
(c) sp and sp 2
(d) sp and sp 2

Solution

Since C1 has two pi bonds, its hybridisation is sp. 1 2 3

N C ___ CH CH2
Since C2 has one pi bond, its hybridisation is sp2. sp sp2 sp2
Therefore, the correct answer is option (c).

Based on the number of pi bonds

H3C H H H
What is the total number of π-bond electrons in the
given structure?
(a) 12 (b) 16 H3C CH3
(c) 4 (d) 8 H
H2C H3C

Solution

Since 1 pi bond has 2 electrons, we get,

Number of pi electrons = Number of pi bonds × 2
In the given structure,
Number of pi bonds = 4
Number of pi electrons = 4 × 2 = 8
Therefore, the correct answer is option (d).

Based on the molecular formula

Which of the following pairs of compounds have the same molecular formula?
(a) (b)
and and
N
N
H
(c) (d)
CH2 CH___ CH3 and and

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Solution

(a) Since both the compounds have different numbers of carbon atoms, their molecular formulae
cannot be the same.
(b) Since both the compounds have different numbers of carbon atoms, their molecular formulae
can not be the same
(c) Both the compounds have the same molecular formula, i.e., C3H6.
(b) Here, one of the compounds has three pi bonds, while the other compound has only sigma
bonds. Thus, their molecular formulae cannot be the same.
Therefore, the correct answer is option (c).

Based on the classification of organic compounds

What type of compound is alicyclic?

(a) Aromatic compound (b) Aliphatic compound
(c) Heterocyclic compound (d) Aliphatic cyclic compound

Solution

Alicyclic compounds are aliphatic cyclic compounds.

Thus, the correct answer is option (d).

Based on the number of sigma bonds

What is the total number of sigma bonds present in the given structural formula of a compound?
H2C C CH __CH2__ C C __CH2__ NH2
(a) 16 (b) 13 (c) 15 (d) 12

Solution

There are seven C __ H, two N__ H, six C__ C, and one C__ N sigma bonds. So, there are a total of
16 sigma bonds.
Therefore, option (a) is the correct answer.

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