3.4.6

Acyl Chlorides & Acylation

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Formation of Acyl Chlorides

Acyl chlorides can be produced by reacting carboxylic acids with an inorganic compound called thionyl chloride (sulphur dichloride oxide).

Acyl chlorides

Acyl chlorides

Acyl chlorides can be derived from carboxylic acids.
- Acyl chlorides are also known as acid chlorides.

Carboxylic acid to acyl chloride

Carboxylic acid to acyl chloride

Acyl chlorides are produced from a reaction between sulphur dichloride oxide (SOCl₂) and a carboxylic acid.
- Hydrogen chloride and sulphur dioxide gases are produced in the reaction.

Obtaining purity

Obtaining purity

Fractional distillation can be used to remove excess reagents from the acyl chloride.
- Hydrogen chloride and sulphur dioxide are given off as gases.

Acylation

Acylation reactions can be used to produce a variety of organic compounds, like amides.

Compounds

Compounds

The above compounds are examples of acylated materials.

Nucleophilic addition-elimination

Nucleophilic addition-elimination

The nucleophilic addition-elimination reaction happens with acyl chlorides and acid anhydrides.
It is used to produce amides, carboxylic acids, and esters.
An example is the production of ethyl ethanoate from ethanoyl chloride (an acyl chloride) with ethanol.
- Ethanoyl chloride reacts with cold ethanol in a highly exothermic reaction. HCl is evolved as a gas and ethyl ethanoate is produced:
- The overall reaction and mechanism is shown on the next slide.

Mechanism

Mechanism

Phenyl benzoate

Phenyl benzoate

Another example of such a reaction is the production of phenyl benzoate.
Phenol (C₆H₅OH) reacts with benzoyl chloride (C₆H₅COCl) in the presence of NaOH and heat to produce phenyl benzoate.
The equation for this reaction is shown below:
- C₆H₅OH + C₆H₅COCl → C₆H₅COOC₆H₅ + HCl

1

Physical Chemistry

1.1

Atoms, Molecules & Stoichiometry

1.1.1Relative Masses 1.1.2The Mole 1.1.3Mass Spectrometry 1.1.4Empirical & Molecular Formulae 1.1.5Balanced Equations 1.1.6Molar Volume 1.1.7End of Topic Test - Amount of Substance

1.2

Atomic Structure

1.2.1Fundamental Particles 1.2.2Isotopes & Mass Number 1.2.3Electron Shells, Sub-Shells & Orbitals 1.2.4Electron Configuration 1.2.5Ionisation Energy 1.2.6Factors Affecting Ionisation Energies 1.2.7Trends of Ionisation 1.2.8Specific Impacts on Ionisation Energies 1.2.9Electron Affinity 1.2.10End of Topic Test - Atomic Structure 1.2.11A-A* (AO2/3) - Atomic Structure

1.3

Chemical Bonding

1.3.1Ionic Bonding 1.3.2Covalent & Dative Bonding 1.3.3Shapes of Molecules 1.3.4Intermolecular Forces 1.3.5Intermolecular Forces 2 1.3.6Electronegativity 1.3.7Bond Length, Bond Energy, & Bond Polarity 1.3.8Metallic Bonding 1.3.9Physical Properties 1.3.10End of Topic Test - Bonding 1.3.11A-A* (AO2/3) - Bonding

1.4

States of Matter

1.4.1Simple Covalent Molecules 1.4.2The Ideal Gas Equation 1.4.3States of Matter 1.4.4Particle Diagrams 1.4.5The Liquid State 1.4.6Giant Ionic Lattices 1.4.7Giant Metallic Lattices 1.4.8Giant Covalent Structures 1.4.9Graphene & Fullerene 1.4.10Recycling

1.5

Chemical Energetics

1.5.1Calorimetry 1.5.2Bond Enthalpies 1.5.3Enthalpy Changes 1.5.4Hess' Law 1.5.5Born-Haber Cycles 1.5.6Born-Haber Cycle Calculations 1.5.7Entropy 1.5.8Free Energy 1.5.9End of Topic Test - Energetics

1.6

Electrochemistry

1.6.1Electrochemical Cells 1.6.2Electrochemical Series 1.6.3Commercial Application 1.6.4Nernst Equation 1.6.5Redox

1.7

Equilibria

1.7.1Dynamic Equilibrium & Le Chatelier 1.7.2Kc 1.7.3Kp 1.7.4pH 1.7.5The Ionic Product of Water 1.7.6Weak Acids & Bases 1.7.7Introduction to Solubility Equilibria 1.7.8Solubility Equilibria Calculations 1.7.9Free Energy of Dissolution 1.7.10pH and Solubility 1.7.11Common-Ion Effect 1.7.12End of Topic Test - Kp & Electrochemistry 1.7.13A-A* (AO2/3) - Electrochemical Cells

1.8

Partition Coefficient

1.9

Reaction Kinetics

1.9.1Collision Theory 1.9.2Orders, Rate Constants & Equations 1.9.3Rate Graphs 1.9.4Rate Determining Step 1.9.5Maxwell-Boltzmann Distribution 1.9.6Catalysts 1.9.7Homogeneous Catalysts 1.9.8Heterogeneous Catalysts 1.9.9End of Topic Test - Kinetics 1.9.10End of Topic Test - Rate Equations 1.9.11A-A* (AO2/3) - Rate Equations

2

Inorganic Chemistry

2.1

The Periodic Table

2.1.1The Periodic Table 2.1.2Trends in the Periodic Table 2.1.3End of Topic Test - Periodicity & Trends 2.1.4Ceramics 2.1.5Period 3 Elements & Oxides 2.1.6Period 3 Oxides 2.1.7End of Topic Test - Period 3

2.2

Group 2

2.2.1Group 2 Chemistry

2.3

Group 17

2.3.1Introduction to Halogens 2.3.2Reactions of Halogens 2.3.3Chlorine & Chlorate(I)2.3.4End of Topic Test - Group 17 2.3.5A-A* (AO2/3) - Periodicity, Group 2 & 17

2.4

Transition Metals

2.4.1General Properties 2.4.2Titrations 2.4.3Shapes of Complex Ions 2.4.4Variable Oxidation States 2.4.5Ligands 2.4.6Colours of Ions 2.4.7Stereoisomerism of Complex Ions 2.4.8Cisplatin 2.4.9Ligand Substitutions & Kstab 2.4.10End of Topic Test - Transition Metals 2.4.11A-A* (AO2/3) - Transition Metals

2.5

Nitrogen & Sulfur

2.5.1Nitrogen & Ammonia 2.5.2Formulated vs Manure Fertilisers 2.5.3Nitrogen Containing Fertilisers 2.5.4Fertilizers & Eutrophication 2.5.5Common Atmospheric Pollutants & Their Properties 2.5.6Catalytic Converters 2.5.7Atmospheric Oxides

3

Organic Chemistry & Analysis

3.1

Introduction to Organic Chemistry

3.1.1Naming Conventions 3.1.2Mechanism 3.1.3Isomerism 3.1.4End of Topic Test - Introduction to Organic Chem

3.2

Hydrocarbons

3.2.1Fractional Distillation 3.2.2Cracking 3.2.3Combustion 3.2.4Chlorination 3.2.5End of Topic Test - Alkanes 3.2.6Introduction to Alkenes 3.2.7Reactions of Alkenes 3.2.8Polymerisation Reactions 3.2.9End of Topic Test - Alkenes 3.2.10Arenes 3.2.11Evidence for Structure of Arenes 3.2.12Reactions of Benzene 3.2.13End of Topic Test -Arenes

3.3

Halogen Derivatives

3.3.1Properties of Haloalkanes 3.3.2Substitution Reactions of Haloalkanes 3.3.3Environmental Impacts of Haloalkanes 3.3.4End of Topic Test - Halogenoalkanes

3.4

Hydroxy Compounds

3.4.1Types of Alcohol 3.4.2Oxidation 1 3.4.3Oxidation 2 3.4.4Elimination 3.4.5Acids & Esters 3.4.6Acyl Chlorides & Acylation 3.4.7Phenols & Their Reactions 3.4.8End of Topic Test - Alcohols

3.5

Carbonyl Compounds

3.5.1Carbonyls 3.5.2Hydrogen Bonding & Carbonyls 3.5.3Aldehydes & Ketones 3.5.4Tri-Iodomethane Reaction 3.5.5End of Topic Test -Carbonyls

3.6

Carboxylic Acids & Derivatives

3.6.1Properties of Carboxylic Acids 3.6.2Esters 3.6.3Acyl Chlorides 3.6.4End of Topic Test - Carboxylic Acids

3.7

Nitrogen Compounds

3.7.1Nature & Preparation of Amines 3.7.2Basicity & Nucleophilicity 3.7.3Amides 3.7.4Reactions of Amino Acids 3.7.5Amino Acids

3.8

Polymerisation

3.8.1Properties of Addition Polymers 3.8.2Condensation Polymerisation 3.8.3Effects of Side-Chains on Polymers 3.8.4Hydrolysis of Ester & Amide Groups 3.8.5Proteins 3.8.6DNA 3.8.7Adhesive & Conducting Polymers 3.8.8End of Topic Test - Amines & Proteins

3.9

Analytical Techniques

3.9.1Chromatography 3.9.2High-Performance Liquid Chromatography 3.9.3Gas Chromatography 3.9.4IR Spectroscopy 3.9.5Uses of IR Spectroscopy 3.9.6Mass Spectrometry 3.9.7Mass Spectrometry Analysis 3.9.8Nuclear Magnetic Resonance 3.9.9Carbon-13 NMR 3.9.10Proton NMR I 3.9.11Proton NMR II 3.9.12End of Topic Test - Analytical Techniques 3.9.13A-A* (AO2/3) - Analytical Techniques

3.10

Organic Synthesis

3.10.1Chirality & Drug Synthesis 3.10.2Organic Synthesis 3.10.3Examples of Synthetic Routes 3.10.4End of Topic Test - Organic Synthesis

Jump to other topics

1

Physical Chemistry

1.1

Atoms, Molecules & Stoichiometry

1.1.1Relative Masses 1.1.2The Mole 1.1.3Mass Spectrometry 1.1.4Empirical & Molecular Formulae 1.1.5Balanced Equations 1.1.6Molar Volume 1.1.7End of Topic Test - Amount of Substance

1.2

Atomic Structure

1.2.1Fundamental Particles 1.2.2Isotopes & Mass Number 1.2.3Electron Shells, Sub-Shells & Orbitals 1.2.4Electron Configuration 1.2.5Ionisation Energy 1.2.6Factors Affecting Ionisation Energies 1.2.7Trends of Ionisation 1.2.8Specific Impacts on Ionisation Energies 1.2.9Electron Affinity 1.2.10End of Topic Test - Atomic Structure 1.2.11A-A* (AO2/3) - Atomic Structure

1.3

Chemical Bonding

1.3.1Ionic Bonding 1.3.2Covalent & Dative Bonding 1.3.3Shapes of Molecules 1.3.4Intermolecular Forces 1.3.5Intermolecular Forces 2 1.3.6Electronegativity 1.3.7Bond Length, Bond Energy, & Bond Polarity 1.3.8Metallic Bonding 1.3.9Physical Properties 1.3.10End of Topic Test - Bonding 1.3.11A-A* (AO2/3) - Bonding

1.4

States of Matter

1.4.1Simple Covalent Molecules 1.4.2The Ideal Gas Equation 1.4.3States of Matter 1.4.4Particle Diagrams 1.4.5The Liquid State 1.4.6Giant Ionic Lattices 1.4.7Giant Metallic Lattices 1.4.8Giant Covalent Structures 1.4.9Graphene & Fullerene 1.4.10Recycling

1.5

Chemical Energetics

1.5.1Calorimetry 1.5.2Bond Enthalpies 1.5.3Enthalpy Changes 1.5.4Hess' Law 1.5.5Born-Haber Cycles 1.5.6Born-Haber Cycle Calculations 1.5.7Entropy 1.5.8Free Energy 1.5.9End of Topic Test - Energetics

1.6

Electrochemistry

1.6.1Electrochemical Cells 1.6.2Electrochemical Series 1.6.3Commercial Application 1.6.4Nernst Equation 1.6.5Redox

1.7

Equilibria

1.7.1Dynamic Equilibrium & Le Chatelier 1.7.2Kc 1.7.3Kp 1.7.4pH 1.7.5The Ionic Product of Water 1.7.6Weak Acids & Bases 1.7.7Introduction to Solubility Equilibria 1.7.8Solubility Equilibria Calculations 1.7.9Free Energy of Dissolution 1.7.10pH and Solubility 1.7.11Common-Ion Effect 1.7.12End of Topic Test - Kp & Electrochemistry 1.7.13A-A* (AO2/3) - Electrochemical Cells

1.8

Partition Coefficient

1.9

Reaction Kinetics

1.9.1Collision Theory 1.9.2Orders, Rate Constants & Equations 1.9.3Rate Graphs 1.9.4Rate Determining Step 1.9.5Maxwell-Boltzmann Distribution 1.9.6Catalysts 1.9.7Homogeneous Catalysts 1.9.8Heterogeneous Catalysts 1.9.9End of Topic Test - Kinetics 1.9.10End of Topic Test - Rate Equations 1.9.11A-A* (AO2/3) - Rate Equations

2

Inorganic Chemistry

2.1

The Periodic Table

2.1.1The Periodic Table 2.1.2Trends in the Periodic Table 2.1.3End of Topic Test - Periodicity & Trends 2.1.4Ceramics 2.1.5Period 3 Elements & Oxides 2.1.6Period 3 Oxides 2.1.7End of Topic Test - Period 3

2.2

Group 2

2.2.1Group 2 Chemistry

2.3

Group 17

2.3.1Introduction to Halogens 2.3.2Reactions of Halogens 2.3.3Chlorine & Chlorate(I)2.3.4End of Topic Test - Group 17 2.3.5A-A* (AO2/3) - Periodicity, Group 2 & 17

2.4

Transition Metals

2.4.1General Properties 2.4.2Titrations 2.4.3Shapes of Complex Ions 2.4.4Variable Oxidation States 2.4.5Ligands 2.4.6Colours of Ions 2.4.7Stereoisomerism of Complex Ions 2.4.8Cisplatin 2.4.9Ligand Substitutions & Kstab 2.4.10End of Topic Test - Transition Metals 2.4.11A-A* (AO2/3) - Transition Metals

2.5

Nitrogen & Sulfur

2.5.1Nitrogen & Ammonia 2.5.2Formulated vs Manure Fertilisers 2.5.3Nitrogen Containing Fertilisers 2.5.4Fertilizers & Eutrophication 2.5.5Common Atmospheric Pollutants & Their Properties 2.5.6Catalytic Converters 2.5.7Atmospheric Oxides

3

Organic Chemistry & Analysis

3.1

Introduction to Organic Chemistry

3.1.1Naming Conventions 3.1.2Mechanism 3.1.3Isomerism 3.1.4End of Topic Test - Introduction to Organic Chem

3.2

Hydrocarbons

3.2.1Fractional Distillation 3.2.2Cracking 3.2.3Combustion 3.2.4Chlorination 3.2.5End of Topic Test - Alkanes 3.2.6Introduction to Alkenes 3.2.7Reactions of Alkenes 3.2.8Polymerisation Reactions 3.2.9End of Topic Test - Alkenes 3.2.10Arenes 3.2.11Evidence for Structure of Arenes 3.2.12Reactions of Benzene 3.2.13End of Topic Test -Arenes

3.3

Halogen Derivatives

3.3.1Properties of Haloalkanes 3.3.2Substitution Reactions of Haloalkanes 3.3.3Environmental Impacts of Haloalkanes 3.3.4End of Topic Test - Halogenoalkanes

3.4

Hydroxy Compounds

3.4.1Types of Alcohol 3.4.2Oxidation 1 3.4.3Oxidation 2 3.4.4Elimination 3.4.5Acids & Esters 3.4.6Acyl Chlorides & Acylation 3.4.7Phenols & Their Reactions 3.4.8End of Topic Test - Alcohols

3.5

Carbonyl Compounds

3.5.1Carbonyls 3.5.2Hydrogen Bonding & Carbonyls 3.5.3Aldehydes & Ketones 3.5.4Tri-Iodomethane Reaction 3.5.5End of Topic Test -Carbonyls

3.6

Carboxylic Acids & Derivatives

3.6.1Properties of Carboxylic Acids 3.6.2Esters 3.6.3Acyl Chlorides 3.6.4End of Topic Test - Carboxylic Acids

3.7

Nitrogen Compounds

3.7.1Nature & Preparation of Amines 3.7.2Basicity & Nucleophilicity 3.7.3Amides 3.7.4Reactions of Amino Acids 3.7.5Amino Acids

3.8

Polymerisation

3.8.1Properties of Addition Polymers 3.8.2Condensation Polymerisation 3.8.3Effects of Side-Chains on Polymers 3.8.4Hydrolysis of Ester & Amide Groups 3.8.5Proteins 3.8.6DNA 3.8.7Adhesive & Conducting Polymers 3.8.8End of Topic Test - Amines & Proteins

3.9

Analytical Techniques

3.9.1Chromatography 3.9.2High-Performance Liquid Chromatography 3.9.3Gas Chromatography 3.9.4IR Spectroscopy 3.9.5Uses of IR Spectroscopy 3.9.6Mass Spectrometry 3.9.7Mass Spectrometry Analysis 3.9.8Nuclear Magnetic Resonance 3.9.9Carbon-13 NMR 3.9.10Proton NMR I 3.9.11Proton NMR II 3.9.12End of Topic Test - Analytical Techniques 3.9.13A-A* (AO2/3) - Analytical Techniques

3.10

Organic Synthesis

3.10.1Chirality & Drug Synthesis 3.10.2Organic Synthesis 3.10.3Examples of Synthetic Routes 3.10.4End of Topic Test - Organic Synthesis

Practice questions on Acyl Chlorides & Acylation

Can you answer these? Test yourself with free interactive practice on Seneca — used by over 10 million students.

1
Acyl chlorides are produced by reacting sulphur dichloride oxide and a carboxylic acid.<br>What gases are produced as by-products in the reaction?Multiple choice
2
Which of these are true about the formation of acyl chlorides?True / false
3
Examples of compounds that are acylated:Fill in the list
4
Nucleophilic addition-elimination reactions can produce:Fill in the list
5
The nucleophile for addition-elimination reaction can be:Fill in the list

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Acids & Esters

Phenols & Their Reactions