CARBON AND ITS COMPOUNDS
CARBON AND ITS COMPOUNDS
Except for hydrogen, there are more carbon compounds than any other chemical
element. Compounds of carbon with double bonds and triple bonds are called
unsaturated compounds, while those with carbon-carbon single bonds are called
saturated compounds.
To achieve the electronic configuration of the nearest noble gas, He, if the carbon atom
loses four of its valence electrons, a huge amount of energy is involved. C4+ ion hence
formed, will be highly unstable due to the presence of six protons and two electrons.
If the carbon atom gains four electrons to achieve the nearest electronic configuration of
the noble gas, Ne, C4− ion will be formed. But again, a huge amount of energy is
required. Moreover, in C4+ ions it is difficult for 6 protons to hold 10 electrons. Hence, to
satisfy its tetravalency, carbon shares all four of its valence electrons and forms
covalent bonds.
Ionic Bond
Ionic bonding involves the transfer of valence electron/s, primarily between a metal and
a nonmetal. The electrostatic attractions between the oppositely charged ions hold the
compound together.
Ionic compounds:
There are primarily three ways in which two atoms combine to lose energy and to
become stable. One of the ways is by donating or accepting electrons to complete their
octet configuration. The bond formed by this kind of combination is known as an ionic
bond or electrovalent bond. This kind of bond is formed when one atom gains
electrons while the other atom loses electrons from its outermost level or orbit.
Electrovalent Bond
Electrovalent bonds are produced when electrons are transferred from atoms of one
element to atoms of another element, producing positive and negative ions. The bond
which is formed by the transfer of electrons between the atoms is called electrovalent
bond or ionic bond. Electrovalent bonds are only formed between metals and non-
metals. Electrovalent bonds are not formed between two non-metals.
In simple words electrovalent bond involves the transference of a certain number of
electrons to another dissimilar atom which has a tendency to gain electrons so that both
acquire stable inert gas configurations. The electrostatic attraction always tends to
decrease the potential energy. Hence, the potential energy of the system is much less
than it was before the formation of an ionic bond.
Covalent Bond
A covalent bond is formed when pairs of electrons are shared between two atoms. It is
primarily formed between two same nonmetallic atoms or between nonmetallic atoms
with similar electronegativity.
Carbon cannot gain 4 electrons to become C4-, because it will be tough for 6 protons to hold
10 electrons, and so the atom will become unstable.
Carbon cannot lose 4 electrons to become C4+ because it would require a large amount of
energy to remove out 4 electrons. Also, the C4+ would have only 2 electrons held by the
proton, which will again become unstable.
Carbon cannot gain or donate electrons, so to complete its nearest noble gas
configuration, it shares electrons to form a covalent bond.
Covalent bonding does not result in the formation of new electrons. The bond only pairs
them.
They are very powerful chemical bonds that exist between atoms.
A covalent bond normally contains an energy of about ~80 kilocalories per mole (kcal/mol).
Covalent bonds rarely break spontaneously after it is formed.
Covalent bonds are directional, where the atoms that are bonded showcase specific
orientations relative to one another.
Most compounds having covalent bonds exhibit relatively low melting points and boiling
points.
Compounds with covalent bonds usually have lower enthalpies of vaporisation and fusion.
Compounds formed by covalent bonding don’t conduct electricity due to the lack of free
electrons.
Covalent compounds are not soluble in water.
Therefore,
and
“The principle of attaining the maximum of eight electrons in the valence shell of
atoms is called the octet rule.”
Lewis introduced simple symbols to denote the electrons present in the outer shell of an
atom known as the valence electrons. These symbols are known as Electron Dot
Symbols, and the structure of the compound is known as Lewis Dot Structure.
Dot structure of methane
Electron dot structures of covalent molecules are written with respect to the octet rule.
According to this rule, all the atoms in the molecule will have eight electrons in their
valence shell except the hydrogen atom. Hydrogen will have only two electrons because
only two electrons complete its first shell to attain helium configuration.
Thus the elements of group 17, such as Cl, would share one electron to attain a stable
octet; the elements of group 16, such as O and S, would share two electrons; the
elements of group 15 would share three electrons and so on.
For Example, the oxygen atom, which has six electrons in its valence shell, completes
its octet by sharing its two electrons with two hydrogen atoms to form a water molecule.
Lewis Structure of Water Molecule
Single Bonds
A single bond is formed when only one pair of electrons is shared between the two
participating atoms. It is represented by one dash (-). Although this form of covalent
bond has a smaller density and is weaker than a double and triple bond, it is the most
stable.
For example, the HCL molecule has one hydrogen atom with one valence electron and
one chlorine atom with seven valence electrons. In this case, a single bond is formed
between hydrogen and chlorine by sharing one electron.
Double Bonds
A double bond is formed when two pairs of electrons are shared between the two
participating atoms. It is represented by two dashes (=). Double covalent bonds are
much stronger than single bonds, but they are less stable.
For example, a carbon dioxide molecule has one carbon atom with six valence
electrons and two oxygen atoms with four valence electrons.
To complete its octet, carbon shares two of its valence electrons with one oxygen
atom and two with another oxygen atom. Each oxygen atom shares its two electrons
with carbon, and therefore there are two double bonds in CO2.
Triple Bond
A triple bond is formed when three pairs of electrons are shared between the two
participating atoms. Triple covalent bonds are represented by three dashes (≡) and are
the least stable type of covalent bonds.
For example, in the formation of a nitrogen molecule, each nitrogen atom having five
valence electrons provides three electrons to form three electron pairs for sharing.
Thus, a triple bond is formed between the two nitrogen atoms.
For example, Nonpolar Covalent Bond is found in gas molecules like hydrogen gas,
nitrogen gas, etc.
Polarization of Covalent Bonds
It is observed that in the sigma bonds between two different atoms, the electron cloud is
always closer to the more electronegative of the two atoms participating in the sigma
bond. Due to this, there is a permanent dipole that arises in the bond, and the covalent
bond is said to be polarized.
A double bond is formed between two atoms when four electrons are shared between
them, i.e., one pair of electrons from each participating atom. It is depicted by double
lines between the two atoms.
A triple bond is formed between two atoms when six electrons are shared between
them, i.e., two pairs of electrons from each participating atom. It is depicted by triple
lines between the two atoms.
Bond strength:
– The bond strength of a bond is determined by the amount of energy required to break
a bond.
– The order of bond strengths when it comes to multiple bonds is: Triple bond>double
bond>single bond
– This is to signify that the energy required to break three bonds is higher than that for
two bonds or a single bond.
Bond length:
– Bond length is determined by the distance between nuclei of the two atoms in a bond.
– The order of bond length for multiple bonds is: Triple bond<double bond<single bond
The distance between the nuclei of two atoms is least when they are triple bonded.
In water (H2O), the two hydrogen atoms share one electron each with the oxygen atom
and form two covalent bonds.
Catenation
Catenation is the self-linking property of an element by which an atom forms covalent
bonds with the other atoms of the same element to form straight or branched chains
and rings of different sizes. It is shown by carbon, sulphur and silicon.
S8
In its native state, sulphur shows catenation of up to 8 atoms in the form of S 8 molecule.
It has a puckered ring structure.
Versatile Nature of Carbon
Tetravalency and Catenation The fact that carbon can form single, double, and triple
bonds demonstrate its versatility. It can also form chains, branching chains, and rings
when joined to other carbon atoms.
Hydrogen, oxygen, carbon, and a few additional elements make up organic molecules.
Organic compounds, on the other hand, are significantly more numerous than inorganic
compounds that do not form bonds.
Carbon is a chemical element with the atomic number 6 and the symbol C. It’s a
versatile element that can be found in a wide variety of chemical combinations.
Carbon’s versatility is best appreciated through properties like tetravalency and
catenation.
Tetravalency: Carbon has a valency of four, so it is capable of bonding with four other atoms
of carbon or atoms of some other mono-valent element.
Catenation: The property of a carbon element due to which its atom can join one another to
form long carbon chains is called catenation.
Allotropes of Carbon
– The phenomenon of the existence of the same element in different physical forms with
similar chemical properties is known as allotropy.
– Some elements like carbon, sulphur, phosphorus, etc., exhibit this phenomenon.
– Crystalline allotropes of carbon include diamond, graphite and, fullerene.
– Amorphous allotropes of carbon include coal, coke, charcoal, lamp black and gas
carbon.
Diamond
Diamond has a regular tetrahedral geometry. This is because each carbon is connected
to four neighbouring carbon atoms via single covalent bonds, resulting in a single unit of
a crystal. These crystal units lie in different planes and are connected to each other,
resulting in a rigid three-dimensional cubic pattern of the diamond.
Diamond:
Graphite
In graphite, each carbon atom is bonded covalently to three other carbon atoms, leaving
each carbon atom with one free valency. This arrangement results in hexagonal rings in
a single plane, and such rings are stacked over each other through weak Van der
Waals forces.
Graphite:
C60
C60, also known as Buckminsterfullerene, is the very popular and stable form of the
known fullerenes.
It is the most common naturally occurring fullerene and can be found in small quantities
in soot.
It consists of 60 carbon atoms arranged in 12 pentagons and 20 hexagons, like in a
soccer ball.
Functional Groups
An atom or a group of atoms which, when present in a compound, gives specific
physical and chemical properties to it regardless of the length and nature of the carbon
chain is called a functional group.
(i) Hydroxyl group (-OH): All organic compounds containing -OH group are known as
alcohols. For example, Methanol (CH3OH), Ethanol (CH3−CH2−OH), etc.
(ii) Aldehyde group (-CHO): All organic compounds containing -CHO group are known
as aldehydes. For example, Methanal (HCHO), Ethanal (CH3CHO), etc.
(iii) Ketone group (-C=O): All organic compounds containing (-C=O) group flanked by
two alkyl groups are known as ketones. For example, Propanone (CH3COCH3),
Butanone (CH3COCH2CH3), etc.
(iv) Carboxyl group (-COOH): All organic acids contain a carboxyl group (-COOH).
Hence, they are also called carboxylic acids.
For example, Ethanoic acid (CH3COOH), Propanoic acid (CH3CH2COOH), etc.
(v) Halogen group (F, CI, Br, I): The alkanes in which one or more than one hydrogen
atom is substituted by- X (F, CI, Br or I) are known as haloalkanes. For
example, Chloromethane (CH3Cl), Bromomethane (CH3Br), etc.
Homologous Series
Homologous series constitutes organic compounds with the same general formula, and
similar chemical characteristics but different physical properties. The adjacent members
differ in their molecular formula by −CH2.
Methane, ethane, propane, butane, etc. are all part of the alkane homologous series.
The general formula of this series is CnH2n+2.
Methane (CH4), Ethane (CH3CH3), Propane (CH3CH2CH3), Butane (CH3CH2CH2CH3).
It can be noticed that there is a difference of −CH2 unit between each successive
compound.
Chemical Properties
A chemical property is a property that describes a substance’s ability to undergo a
specific chemical change. We look for a chemical shift to identify a chemical attribute. A
chemical change always results in the formation of one or more types of matter that are
distinct from the matter that existed before the change.
Combustion Reactions
Combustion means the burning of carbon or carbon-containing compounds in the
presence of air or oxygen to produce carbon dioxide, heat and light.
For example,
Flame Characteristics
Saturated hydrocarbons give a clean flame, while unsaturated hydrocarbons give a
smoky flame. In the presence of limited oxygen, even saturated hydrocarbons give
smoky flame.
Addition
The reactions in which two molecules react to form a single product having all the atoms
of the combining molecules are called addition reactions.
The hydrogenation reaction is an example of the addition reaction. In this reaction,
hydrogen is added to a double bond or a triple bond in the presence of a catalyst like
nickel, palladium or platinum.
Substitution
The reaction in which an atom or group of atoms in a molecule is replaced or
substituted by different atoms or groups of atoms is called a substitution reaction. In
alkanes, hydrogen atoms are replaced by other elements.
CH4+Cl2+Sunlight → CH3Cl+HCl
Ethanol
(i) Ethanol, C2H5OH is a colourless liquid having a pleasant smell.
(ii) It boils at 351 K.
(iii) It is miscible with water in all proportions.
(iv) It is a nonconductor of electricity (it does not contain ions)
(v) It is neutral to litmus.
Uses:
Elimination Reaction
An elimination reaction is a type of reaction in which two substituents are removed from
a molecule. These reactions play an important role in the preparation of alkenes.
Dehydration Reaction
Ethanol reacts with concentrated sulphuric acid at 443 K to produce ethylene. This
reaction is known as dehydration of ethanol because, in this reaction, a water molecule
is removed from the ethanol molecule.
CH3CH2OH → CH2=CH2+H2O
Esterification
When a carboxylic acid is refluxed with alcohol in the presence of a small quantity of
conc.H2SO4, a sweet-smelling ester is formed. This reaction of ester formation is called
esterification.
When ethanol reacts with ethanoic acid in the presence of conc.H2SO4, ethyl ethanoate
and water are formed.
CH3COOH+C2H5OH → CH3COOC2H5+H2O
Saponification
A soap is a sodium or potassium salt of long-chain carboxylic acids (fatty acid). The
soap molecule is generally represented as RCOONa, where R = non-ionic hydrocarbon
group and −COO−Na+ ionic group. When oil or fat of vegetable or animal origin is
treated with a concentrated sodium or potassium hydroxide solution, hydrolysis of fat
takes place; soap and glycerol are formed. This alkaline hydrolysis of oils and fats is
commonly known as saponification.
It reacts with a solution of sodium hydroxide to form sodium ethanoate and water.
CH3COOH+NaOH→CH3COONa+H2O
The non-polar hydrophobic part or tail of the soap molecules attracts the dirt or oil part
of the fabric, while the polar hydrophilic part or head,(−COO−Na+, remains attracted to
water molecules.
The agitation or scrubbing of the fabric helps the micelles to carry the oil or dirt particles
and detach them from the fibres of the fabric.
Hard Water
Hard water contains salts of calcium and magnesium, principally as bicarbonates,
chlorides, and sulphates. When soap is added to hard water, calcium and magnesium
ions of hard water react with soap forming insoluble curdy white precipitates of calcium
and magnesium salts of fatty acids.
2C17H35COONa+MgCl2 → (C17H35COO)2Mg+2NaCl
2C17H35COONa+CaCl2 → (C17H35COO)2Ca+2NaCl
These precipitates stick to the fabric being washed and hence, interfere with the
cleaning ability of the soap. Therefore, a lot of soap is wasted if the water is hard.