Electrophilic Addition
1. Electrophiles & Alkenes
An electrophile is an electron pair acceptor.
The carbon-carbon double bond contains a region of high electron density (due to the presence of the π-bond). This negatively charged region attracts electrophiles (electron deficient species).
2. Electrophilic Addition Mechanisms
Answer:
Bromine is more electronegative than hydrogen, creating a polar bond. This results in a permanent dipole (Hδ+-Brδ-). The partially positive hydrogen atom (Hδ+) is attracted to the electron-rich double bond, allowing it to accept an electron pair.
Mechanism:
Answer:
The organic intermediate is a carbocation (positively charged). The inorganic intermediate is a bromide ion (negatively charged with a lone pair). The lone pair on the bromide ion forms a coordinate bond with the positively charged carbon.
Induced Dipole:
As the non-polar Cl₂ molecule approaches the electron-rich C=C bond, the electrons in the double bond repel the electrons in the Cl-Cl bond. This induces a temporary dipole (Clδ+-Clδ-), allowing the Clδ+ to act as an electrophile.
Propene reacts faster.
The reaction with propene proceeds via a secondary carbocation intermediate, whereas ethene proceeds via a primary carbocation. Secondary carbocations are more stable due to the positive inductive effect of two alkyl groups pushing electron density towards the positive charge. A more stable intermediate lowers the activation energy, increasing the rate of reaction.
3. Hydration of Ethene
H⁺ Mechanism:
H₂SO₄ Mechanism:
- HSO₄⁻: Acts as a Base (it accepts a hydrogen ion/proton to regenerate the sulfuric acid catalyst).
- CH₃CH₂CH₂⁺: Acts as an Acid (it donates a hydrogen ion/proton).
Industrial Conditions:
- Temperature: 300°C
- Pressure: 60-70 atm
- Catalyst: Concentrated Phosphoric Acid (H₃PO₄)