Edexcel A-Level Chemistry 9CH0
Atomic Structure and the Periodic Table
Bonding and Structure
Inorganic Chemistry and the Periodic Table
Formulae, Equations and Amounts of Substance
Organic Chemistry I
Modern Analytical Techniques I
Energetics I
Kinetics I
Equilibrium I
Acid-Base Equilibria
Energetics II
Redox II
Transition Metals
Kinetics II
Organic Chemistry II
Organic Chemistry III
Organic Chemistry III
Nitration, halogenation, Friedel-Crafts and phenol
- 3 things to know
- Papers 2 and 3
Overview
The mechanisms of halogenation, nitration and Friedel-Crafts alkylation and acylation of benzene, including how each electrophile forms and each catalyst is regenerated, and why phenol decolourises bromine water to give 2,4,6-tribromophenol without a catalyst.
What you need to know
Answer each one before you reveal it.
What is the formula of the electrophile generated in Friedel-Crafts acylation?
What intermediate is formed when the positive halogen ion attacks benzene during halogenation?
Questions from this subtopic
Each one with the model answer underneath.
- 1
What intermediate is formed when the positive halogen ion attacks benzene during halogenation?
Model answer
A carbocation intermediate.
- 2
How is aromaticity restored in the final step of benzene halogenation?
Model answer
A hydrogen ion is lost and bonds with the halogen carrier complex, regenerating the catalyst and releasing HX.
- 3
What is the formula of the electrophile in the nitration of benzene, and how is it generated?
Model answer
The nitronium ion (NO₂⁺), generated when concentrated sulfuric acid protonates nitric acid, which then loses water.
- 4
What intermediate forms when the nitronium ion attacks benzene?
Model answer
A carbocation intermediate.
- 5
How is the sulfuric acid catalyst regenerated in the nitration mechanism?
Model answer
A hydrogen ion is lost from the carbocation intermediate and regenerates the sulfuric acid.
- 6
In Friedel-Crafts alkylation, how is the carbocation electrophile generated?
Model answer
Aluminium chloride accepts a lone pair from the halogen of the halogenoalkane, generating a carbocation.
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