Mechanism of Addition of Bromine to Ethane: π-complex

Mechanism of Addition of Bromine to Ethane
C2H4 + Br2 → BrCH2CH2Br
This takes the form of 3 main steps shown below
1. Forming of a π-complex
The electrophilic Br-Br molecule interacts with electron-rich alkene molecule to form a π-complex
2. Forming of a three-membered bromonium ion
The alkene is working as an electron donor and bromine as an electrophile. The three-
membered bromonium ion consisted with two carbon atoms and a bromine atom forms with a release of Br−.
3. Attacking of bromide ion
The bromonium ion is opened by the attack of Br− from the back side. This yields the vicinal dibromide with
an antiperiplanar configuration.
Electrophile
Electrophilic means 'electron-loving'. An Electrophile is a chemical species that is electron-deficient. It will seek out an
electron-rich site in an organic molecule.
Examples of electrophiles are: H+, Cl+, Br+, I+, NO2+, CH3+, CH3CO+, C6H5N2+.
The diagram below illustrates the initial attack of the Br+ electrophile on the benzene ring in an electrophilic
substitution reaction. (The curly arrow shows the direction of movement of a pair of electrons.)
Neutrophile
Nucleophilic means 'neucleus-loving'. A Nucleophile is a chemical species that is electron-rich. It will seek out an
electron-deficient site in an organic molecule.
Examples of nucleophiles are: H2O, NH3, OH-, Cl-, Br-, CN-.
The diagram below illustrates a nucleophilic subsitution reaction in which a primary halogenoalkane is refluxed with
dilute aqueous potassium hydroxide solution.
Electromeric Effect
Electromeric effect refers to a temporary polarization between atoms in a multiple bond in the presence of an
attacking reagent. The effect is temporary and it will revert when the reagent is removed.The electron transfer
facilitates the bonding of the attacking group to the atom. If the transfer is towards the attacking group, it is indicated
as +E and if it is away from the attacking group, it is termed as -E.
For example, consider the carbonyl group, >C=O, present in aldehydes and ketones. When a negatively charged
reagent approaches the molecule seeking positive site, it causes instantaneous shift of the bond electron pair of the
C=O bond in carbonyl group to oxygen (which is more electronegative than carbon). The carbon then acquires
positive charge. In the meanwhile oxygen takes complete control of the electron pair and becomes negatively
charged. Therefore, in the presence of attacking reagent, one bond is lost and this negatively charged attacking
reagent links to the carbon having positive charge.
Resonating Effect
resonance or mesomerism is a way of describing delocalized electrons within certain molecules or polyatomic
ions where the bonding cannot be expressed by one single Lewis formula. A molecule or ion with such delocalized
electrons is represented by several contributing structures (also called resonance structures or canonical
forms).
Each contributing structure can be represented by a Lewis structure, with only an integer number of covalent
bonds between each pair of atoms within the structure.

Resonating Structure of Carbonate Ion
These individual contributors cannot be observed in the actual resonance-stabilized molecule; resonance is not a
rapidly-interconverting set of contributors. Several Lewis structures are used collectively to describe the actual
molecular structure. The actual structure is an approximate intermediate between the canonical forms, but its overall
energy is lower than each of the contributors. This intermediate form between different contributing structures is
called a resonance hybrid.
Electron delocalization lowers the potential energy of the substance and thus makes it more stable than any of the
contributing structures. The difference between the potential energy of the actual structure and that of the contributing
structure with the lowest potential energy is called the resonance energy[5] or delocalization energy.
Catenation
Catenation is the ability of a chemical element to form a long chain-like structure via a series of covalent bonds.
Catenation occurs most readily in carbon, which forms covalent bonds with other carbon atoms. Catenation is the
reason for the presence of a large number of organic compounds in nature. Carbon is most well known for its
properties of catenation
The ability of an element to catenate is primarily based on the bond energy of the element to itself.
Other elements which have the ability of catenation are
1. Sulphur:
2. Selenium
3. Tellurium
4. Silicon
AlCl3
Aluminium chloride is a covalent bond.
Actually in true sense it is a ionic bond with a higher degree of co-

valency due to polarization.
But when Aluminium Chloride reacts with water:

Aluminium chloride has a high affinity for water and forms the hexahydrate AlCl3·6H2O.
Aqueous solutions of AlCl3 are ionic and thus conduct electricity well.
Such solutions are found to be acidic, indicative of partial hydrolysis of the Al3+ ion.
The reactions can be described (simplified) as:
[Al(H2O)6]3+ ⇌ [Al(OH)(H2O)5]2+ + H+
Aqueous solutions behave similarly to other aluminium salts containing hydrated Al3+ ions and hence even
though Alcl3 is covalent its aqueous solution is ionic.
BF3 & BH3

BF3 flourine has 3 lone pair of electrons.
Structure of BF3
The high amount of electronegativity of flourine hels stabilize BF3.
Moreover we may also find resonance structures for BF3.
But in BH3 the stablility cannot be achieved.
Hence BF3 is more stable than BH3.
Because of its instability BH3 exists as a dimer, B2H6, where elextrons are shared between each of the monomers.
Structure of B2H6

Mechanism of Addition of Bromine to Ethane: π-complex

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Mechanism of Addition of Bromine to Ethane

C2H4 + Br2 → BrCH2CH2Br

This takes the form of 3 main steps shown below

2. Forming of a three-membered bromonium ion

3. Attacking of bromide ion

as +E and if it is away from the attacking group, it is termed as -E.

reagent links to the carbon having positive charge.

resonance or mesomerism is a way of describing delocalized electrons within certain molecules or polyatomic

electrons is represented by several contributing structures (also called resonance structures or canonical

bonds between each pair of atoms within the structure.

called a resonance hybrid.

Other elements which have the ability of catenation are

Aluminium chloride is a covalent bond.

Actually in true sense it is a ionic bond with a higher degree of co-

But when Aluminium Chloride reacts with water:

Aqueous solutions of AlCl3 are ionic and thus conduct electricity well.

Such solutions are found to be acidic, indicative of partial hydrolysis of the Al3+ ion.

The reactions can be described (simplified) as:

Aqueous solutions behave similarly to other aluminium salts containing hydrated Al3+ ions and hence even

though Alcl3 is covalent its aqueous solution is ionic.

BF3 & BH3

The high amount of electronegativity of flourine hels stabilize BF3.

Moreover we may also find resonance structures for BF3.

But in BH3 the stablility cannot be achieved.

Hence BF3 is more stable than BH3.

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