6.5.1
Electrophilic Substitution
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Electrophilic Substitution of Benzene
Electrophilic substitution reactions can be used to introduce halogens or nitro (NO2) groups onto a benzene ring.
Nitration of benzene
- In nitration reactions of benzene, benzene reacts with a nitronium ion, NO2+, which is produced from the reaction of nitric acid with sulphuric acid.
- Sulphuric acid acts as an acid catalyst and the reaction requires heating to 50°C.
Chlorination of benzene
- The chlorination reaction requires a Lewis acid catalyst such as AlCl3 and a dry solvent, which is normally ether.
General mechanism of electrophilic substitution
- Electrophiles are attracted to the high electron density of the benzene ring.
- The attack of an electrophile on benzene breaks up the continuous cycle of delocalised electrons to form a positively charged intermediate.
- This intermediate is unstable as it loses aromaticity.
- A hydrogen ion (H+) is then lost from the non-aromatic intermediate to regain the complete delocalisation of electrons over the six carbons.
Nitration (mechanism)
- The electrophile is the nitronium ion (NO2+).
- The nitronium ion is formed by an acid-base reaction in which sulphuric acid acts as an acid and nitric acid, the weaker of the two acids, as a base:
- HNO3(aq) + 2H2SO4(aq) → NO2+(aq) + 2HSO4-(aq) + H3O+(aq)
Nitration (mechanism) cont.
- On the formation of nitronium (NO2+), which is the electrophile, the reaction mechanism is analogous to the general mechanism.
- The sulphuric acid is a catalyst as it is regenerated by protonation of HSO4- in the final step.
1Structure - Models of the Particulate of Matter
1.1Introduction to the Particulate Model of Matter
1.2The Nuclear Atom
1.3Electron Configuration
1.4Counting Particles by Mass: The Mole
1.6Elements, Compounds & Mixtures
1.7States of Matter & Changes of State
1.8Reacting Masses &. Volumes
1.9Solutions
2Structure - Models of Bonding & Structure
2.1The Ionic Model
2.2The Covalent Model
2.3Covalent Structures
2.4The Metallic Model
2.5From Models to Materials
2.6Valence Electrons & Ionic Compounds
2.7Molecular Shape
3Structure - Classification of Matter
3.1The Periodic Table: Classification of Elements
3.2Periodic Trends
3.3Group 1 Alkali Metals
3.4Halogens
3.5Noble gases, group 18
3.6Functional Groups: Classification of Organic
3.7Functional Group Chemistry
3.8Alkanes
3.9Alcohols
4Reactivity - What Drives Chemical Reaction?
4.1Endothermic & Exothermic Reactions
4.2Enthalpy of Reaction, Formation, & Hess' Law
5Reactivity - How Much, How Fast & How Far?
5.1Kinetics
5.2Rates of Reaction
5.3Stoichometry
5.4Le Châtelier’s Principle
5.5Introduction to Equilibrium
5.6Equilibrium Constant
5.7Reaction Quotient & Equilibrium Constant
6Reactivity - The Mechanisms of Chemical Change
6.1Proton Transfer Reactions
6.2The pH Scale
6.3Strong & Weak Acids and Bases
6.4Acid Deposition
6.5Types of Organic Reactions
6.6Oxidation & Reduction
6.7Electrochemical Cells
6.9Acid-Base Titrations
6.9.1Titration Calculation Weak Acid & Strong Base6.9.2Titration Experimental Detail6.9.3Extended Response - Titration6.9.4Titration Calculations6.9.5Titration Curves6.9.6Titration Calculation Strong Acid & Weak Base6.9.7IB Multiple Choice - Titrations6.9.8Polyprotic Acids6.9.9Titration Calculations Strong Acid & Strong Base6.9.10Titrations Curves 2
7Measurement, Data Processing & Analysis
7.1Uncertainties & Errors in Measurements & Results
7.2Graphical Techniques
7.3Spectroscopic Identification of Organic Compounds
7.4Infrared Spectroscpy
Jump to other topics
1Structure - Models of the Particulate of Matter
1.1Introduction to the Particulate Model of Matter
1.2The Nuclear Atom
1.3Electron Configuration
1.4Counting Particles by Mass: The Mole
1.6Elements, Compounds & Mixtures
1.7States of Matter & Changes of State
1.8Reacting Masses &. Volumes
1.9Solutions
2Structure - Models of Bonding & Structure
2.1The Ionic Model
2.2The Covalent Model
2.3Covalent Structures
2.4The Metallic Model
2.5From Models to Materials
2.6Valence Electrons & Ionic Compounds
2.7Molecular Shape
3Structure - Classification of Matter
3.1The Periodic Table: Classification of Elements
3.2Periodic Trends
3.3Group 1 Alkali Metals
3.4Halogens
3.5Noble gases, group 18
3.6Functional Groups: Classification of Organic
3.7Functional Group Chemistry
3.8Alkanes
3.9Alcohols
4Reactivity - What Drives Chemical Reaction?
4.1Endothermic & Exothermic Reactions
4.2Enthalpy of Reaction, Formation, & Hess' Law
5Reactivity - How Much, How Fast & How Far?
5.1Kinetics
5.2Rates of Reaction
5.3Stoichometry
5.4Le Châtelier’s Principle
5.5Introduction to Equilibrium
5.6Equilibrium Constant
5.7Reaction Quotient & Equilibrium Constant
6Reactivity - The Mechanisms of Chemical Change
6.1Proton Transfer Reactions
6.2The pH Scale
6.3Strong & Weak Acids and Bases
6.4Acid Deposition
6.5Types of Organic Reactions
6.6Oxidation & Reduction
6.7Electrochemical Cells
6.9Acid-Base Titrations
6.9.1Titration Calculation Weak Acid & Strong Base6.9.2Titration Experimental Detail6.9.3Extended Response - Titration6.9.4Titration Calculations6.9.5Titration Curves6.9.6Titration Calculation Strong Acid & Weak Base6.9.7IB Multiple Choice - Titrations6.9.8Polyprotic Acids6.9.9Titration Calculations Strong Acid & Strong Base6.9.10Titrations Curves 2
7Measurement, Data Processing & Analysis
7.1Uncertainties & Errors in Measurements & Results
7.2Graphical Techniques
7.3Spectroscopic Identification of Organic Compounds
7.4Infrared Spectroscpy
Practice questions on Electrophilic Substitution
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