Eduqas A-Level Chemistry A410QS
Formulae and Equations
Basic Ideas About Atoms
Chemical Calculations
Bonding
Solid Structures
The Periodic Table
Simple Equilibria and Acid-Base Reactions
Thermochemistry
Rates of Reaction
The Wider Impact of Chemistry
Organic Compounds
Hydrocarbons
Halogenoalkanes
Alcohols and Carboxylic Acids
Instrumental Analysis
Redox and Standard Electrode Potential
Redox Reactions
Chemistry of the P-Block
Chemistry of the D-Block Transition Metals
Chemical Kinetics
Enthalpy Changes for Solids and Solutions
Entropy and Feasibility of Reactions
Equilibrium Constants
Acid-Base Equilibria
Stereoisomerism
Aromaticity
Alcohols and Phenols
Aldehydes and Ketones
Carboxylic Acids and Their Derivatives
Amines
Amino Acids, Peptides and Proteins
Organic Synthesis and Analysis
Specified Practical Work
Practical Skills and Techniques
Mathematical Skills in Chemistry
Aromaticity
Friedel-Crafts alkylation and the ring's interaction with substituents
- 3 things to know
- Component 2
Overview
How aluminium chloride is regenerated in a Friedel-Crafts alkylation and general principle about arenes that the behaviour of chlorobenzene illustrates.
What you need to know
Answer each one before you reveal it.
State the reagents and conditions for the Friedel-Crafts alkylation of benzene with chloromethane.
Name the electrophile in the Friedel-Crafts alkylation of benzene by chloromethane and give the equation for its formation.
Questions from this subtopic
Each one with the model answer underneath.
- 1
State the reagents and conditions for the Friedel-Crafts alkylation of benzene with chloromethane.
Model answer
Chloromethane and anhydrous aluminium chloride, heated under reflux at about 50 °C with all the apparatus dry.
- 2
Name the electrophile in the Friedel-Crafts alkylation of benzene by chloromethane and give the equation for its formation.
Model answer
The electrophile is the methyl carbocation, CH₃⁺, formed by CH₃Cl + AlCl₃ → CH₃⁺ + AlCl₄⁻.
- 3
Give the overall equation for the Friedel-Crafts alkylation of benzene with chloromethane and name the product.
Model answer
C₆H₆ + CH₃Cl → C₆H₅CH₃ + HCl, and the product is methylbenzene.
- 4
Explain how aluminium chloride is regenerated in a Friedel-Crafts alkylation.
Model answer
The proton lost from the ring is taken up by the tetrachloroaluminate ion, AlCl₄⁻ + H⁺ → AlCl₃ + HCl, so only a small amount of aluminium chloride is needed.
- 5
Why must a Friedel-Crafts alkylation be carried out in dry apparatus?
Model answer
Aluminium chloride is rapidly hydrolysed by water, which destroys the halide acceptor so that no carbocation can be generated and the reaction stops.
- 6
Why is Friedel-Crafts alkylation valuable to a synthetic chemist?
Model answer
It forms a new carbon–carbon bond, so it lengthens the carbon skeleton attached to the ring. Ethylbenzene made this way is the feedstock for phenylethene and hence for poly(phenylethene).
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