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
Electrophilic substitution: nitration and halogenation
- 3 things to know
- Component 2
Overview
Reaction type characteristic of arenes, intermediate formed when an electrophile bonds to benzene and electrophile in nitration and give the equation for its formation.
What you need to know
Answer each one before you reveal it.
Describe the second step of electrophilic substitution in benzene, saying what the curly arrow moves.
Which reagents nitrate benzene, and at what temperature is the mixture held?
Questions from this subtopic
Each one with the model answer underneath.
- 1
Name the reaction type characteristic of arenes.
Model answer
Electrophilic substitution.
- 2
Why is benzene attacked by electron-deficient species rather than by nucleophiles?
Model answer
The delocalised π system forms a region of high electron density above and below the plane of the ring, which attracts anything short of electrons and repels anything carrying a lone pair or negative charge.
- 3
Describe the first step of electrophilic substitution in benzene, saying what each curly arrow moves.
Model answer
A curly arrow runs from the delocalised π system of the ring to the electrophile, donating a pair of electrons to form a σ bond between one ring carbon and the electrophile.
- 4
Describe the intermediate formed when an electrophile bonds to benzene.
Model answer
It is a positively charged intermediate in which the carbon now bearing the electrophile has become sp³ and has dropped out of the delocalised system, leaving four π electrons spread over the remaining five carbon atoms and a positive charge shared round the ring.
- 5
Describe the second step of electrophilic substitution in benzene, saying what the curly arrow moves.
Model answer
A curly arrow runs from the bonding pair of the C—H bond at the substituted carbon back into the ring. The hydrogen leaves as H⁺ and the full delocalised system of six electrons is restored.
- 6
Explain why the intermediate loses H⁺ instead of gaining a negative ion.
Model answer
Losing a proton restores the ring of six delocalised electrons and recovers about 152 kJ mol⁻¹ of stability, whereas capturing an anion would leave the delocalisation permanently broken.
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