Electrophilic Addition Reactions Questions

Electrophilic Addition

Alkenes Worksheet

1. Electrophiles & Alkenes

1. Define the term electrophile.

An electrophile is an electron pair acceptor.

2. Explain why alkenes can undergo electrophilic attack.

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

3. Hydrogen bromide can react with ethene in an electrophilic addition reaction.
3a. Explain why hydrogen bromide is an electrophile.

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.

3b. Outline the mechanism for the reaction between HBr and C₂H₄.

Mechanism:

Mechanism of HBr reacting with Ethene
3c. Explain why the organic intermediate formed can be attacked by the inorganic intermediate.

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.

4. Chlorine can also react with alkenes.
4a. Explain why chlorine can react with alkenes.

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.

4b. Both ethene and propene will react with chlorine. State which reaction will occur faster and explain why.

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

5. Ethanol can be produced from ethene by reacting ethene and water in the presence of an acid catalyst.
5a. Outline the mechanism using H⁺ to represent the catalyst.

H⁺ Mechanism:

Hydration mechanism with H+
5b. Outline the mechanism using H₂SO₄ to represent the catalyst.

H₂SO₄ Mechanism:

Hydration mechanism with Sulfuric Acid
5c. State how HSO₄⁻ and CH₃CH₂CH₂⁺ are behaving in these mechanisms.
  • 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).
5d. State the conditions used in the reaction as an industrial process.

Industrial Conditions:

  • Temperature: 300°C
  • Pressure: 60-70 atm
  • Catalyst: Concentrated Phosphoric Acid (H₃PO₄)