Substitution Reactions

Halogenoalkanes

A halogenoalkane is a halogenated alkane. This means that one (or more) of the hydrogen atoms in an alkane has been replaced by a halogen atom.

Names of halogenoalkanes

The names of halogenoalkanes use the halogen names at the start.
- E.g. Fluoromethane.
- E.g. Chloromethane.
- E.g. Bromomethane.
- E.g. Iodomethane.

Properties of halogenoalkanes

Halogenoalkanes are polar molecules and contain polar bonds.
The polar bonds are important in their reactions.
Because halogens are more electronegative than carbon, the carbon atoms carry a partial positive charge and the halogen atoms carry a partial negative charge.
Halogenoalkanes undergo substitution reactions with ammonia, hydroxide ions, and cyanide ions.

Nucleophiles and electrophiles

A nucleophile is a molecule that is attracted to a nucleus.
- Nuclei have positive charges, so nucleophiles tend to be negatively charged.
- Molecules with lone pairs are also nucleophilic.
An electrophile is a molecule that is attracted to a pair of electrons.
- Electrons have negative charges, so electrophiles tend to be positively charged.

Nucleophilic Substitution

Halogenoalkanes react with nucleophiles in a nucleophilic substitution reaction. This mechanism is a one-step process.

Nucleophilic substitution

The mechanism for nucleophilic substitution with hydroxide ions is shown above.
- This makes an alcohol.

With ammonia

Nucleophilic substitution can be used to make amines. This is shown above.

With cyanide ions

Nucleophilic substitution can be used to make nitriles. This is shown above.

Reactivity

The reactivity of halogenoalkanes decreases in the order I>Br>Cl>F.
This is because the C-I bond is weakest and the C-F bond is strongest.
For the halogenoalkane to react, the C-X bond must break (X means any halogen).
This means that the activation energy is highest for a halogenoalkane with a carbon-fluorine bond and the reaction is therefore slowest.

1Physical Chemistry

1.1Atomic Structure

1.1.1Fundamental Particles

1.1.2Isotopes & Mass Number

1.1.3Mass Spectrometry

1.1.4Electron Shells, Sub-Shells & Orbitals

1.1.5Electron Configuration

1.1.6Ionisation Energy

1.1.7Factors Affecting Ionisation Energies

1.1.8Trends of Ionisation

1.1.9Specific Impacts on Ionisation Energies

1.1.10End of Topic Test - Atomic Structure

1.1.11A-A* (AO3/4) - Atomic Structure

1.2Amount of Substance

1.2.1Relative Masses

1.2.2The Mole

1.2.3The Ideal Gas Equation

1.2.4Empirical & Molecular Formulae

1.2.5Balanced Equations

1.2.6Percentage Yield

1.2.7A-A* (AO3/4) - Percentage Yield

1.2.8Atom Economy

1.2.9End of Topic Test - Amount of Substance

1.2.10A-A* (AO3/4) - Substances & Yield

1.3Bonding

1.3.1Ionic Bonding

1.3.2Covalent & Dative Bonding

1.3.3Carbon Structures

1.3.4Metallic Bonding

1.3.5Physical Properties

1.3.6Shapes of Molecules

1.3.7Polarity

1.3.8Intermolecular Forces

1.3.9Intermolecular Forces 2

1.3.10End of Topic Test - Bonding

1.3.11Exam-Style Question - Shape of Molecules

1.3.12A-A* (AO3/4) - Bonding

1.4Energetics

1.4.1Enthalpy Changes

1.4.2Calorimetry

1.4.3Hess' Law

1.4.4Bond Enthalpies

1.4.5End of Topic Test - Energetics

1.5Kinetics

1.5.1Collision Theory

1.5.2Maxwell-Boltzmann Distribution

1.5.3Increasing Rates

1.5.4End of Topic Test - Kinetics

1.6Equilibria

1.6.1Le Chatelier

1.6.2Equilibrium Constants

1.6.3A-A* (AO3/4) - Energetics, Kinetics, Equilibria

1.6.4End of Topic Test - Equilibria

1.7Redox

1.7.1Redox

1.7.2End of Topic Test - Redox

2Physical Chemistry 2 (A2 Only)

2.1Thermodynamics (A2 Only)

2.1.1Born-Haber Cycles (A2 Only)

2.1.2Born-Haber Cycle Calculations (A2 Only)

2.1.3Entropy (A2 Only)

2.1.4Free Energy (A2 Only)

2.1.5End of Topic Test - Thermodynamics

2.1.6A-A* (AO3/4) - Thermodynamics

2.2Rate Equations (A2 Only)

2.2.1Rate Equations (A2 Only)

2.2.2Rate Equations 2 (A2 Only)

2.2.3The Arrhenius Equation (A2 Only)

2.2.4Experimental Methods for Rates (A2 Only)

2.2.5End of Topic Test - Rate Equations

2.2.6Exam-Style Question - Rates

2.2.7A-A* (AO3/4) - Rate Equations

2.3The Equilibrium Constant Kp (A2 Only)

2.3.1Properties of Kp (A2 Only)

2.4Electrochemical Cells (A2 Only)

2.4.1Electrochemical Cells (A2 Only)

2.4.2Electrochemical Series (A2 Only)

2.4.3Commercial Application (A2 Only)

2.4.4End of Topic Test - Kp & Electrochemistry

2.4.5A-A* (AO3/4) - Electrochemical Cells

2.5Acids & Bases (A2 Only)

2.5.1Brønsted-Lowry Acids & Bases (A2 Only)

2.5.2pH (A2 Only)

2.5.3The Ionic Product of Water (A2 Only)

2.5.4Weak Acids & Bases (A2 Only)

2.5.5pH Curves & Titrations (A2 Only)

2.5.6pH Curves & Titrations 2 (A2 Only)

2.5.7Buffer Solutions (A2 Only)

2.5.8End of Topic Test - Acids & Bases

2.5.9Exam-Style Question - Weak Acids

2.5.10A-A* (AO3/4) - Acids & Bases

3Inorganic Chemistry

3.1Periodicity & Trends

3.1.1The Periodic Table

3.1.2Trends in the Periodic Table

3.1.3End of Topic Test - Periodicity & Trends

3.2Group 2

3.2.1Group 2 Chemistry

3.2.2End of Topic Test - Group 2

3.3Group 7

3.3.1Introduction to Halogens

3.3.2Reactions of Halogens

3.3.3Chlorine & Chlorate(I)

3.3.4End of Topic Test - Group 7

3.3.5Exam-Style Question - Group 7

3.3.6A-A* (AO3/4) - Periodicity, Group 2 & 7

4Inorganic Chemistry 2 (A2 Only)

4.1Period 3 (A2 Only)

4.1.1Period 3 Elements & Oxides (A2 Only)

4.1.2Period 3 Oxides (A2 Only)

4.1.3End of Topic Test - Period 3

4.2Transition Metals (A2 Only)

4.2.1General Properties (A2 Only)

4.2.2Substitution Reactions (A2 Only)

4.2.3Shapes of Complex Ions (A2 Only)

4.2.4Colours of Ions (A2 Only)

4.2.5Variable Oxidation States (A2 Only)

4.2.6Titrations (A2 Only)

4.2.7Homogeneous Catalysts (A2 Only)

4.2.8Heterogeneous Catalysts (A2 Only)

4.2.9End of Topic Test - Transition Metals

4.2.10A-A* (AO3/4) - Transition Metals

4.3Reactions of Ions in Aqueous Solutions (A2 Only)

4.3.1Acidity (A2 Only)

4.3.2Identification (A2 Only)

4.3.3End of Topic Test - Reactions of Ions in Solution

5Organic Chemistry 1

5.1Introduction

5.1.1Naming Conventions

5.1.2Mechanism

5.1.3Isomerism

5.1.4End of Topic Test - Introduction to Organic Chem

5.2Alkanes

5.2.1Fractional Distillation

5.2.2Cracking

5.2.3Combustion

5.2.4Chlorination

5.2.5End of Topic Test - Alkanes

5.3Halogenoalkanes

5.3.1Substitution Reactions

5.3.2Elimination Reactions

5.3.3Ozone Depletion

5.3.4End of Topic Test - Halogenoalkanes

5.4Alkenes

5.4.1Introduction to Alkenes

5.4.2Reactions of Alkenes

5.4.3Polymerisation Reactions

5.4.4Properties of Polymers

5.4.5End of Topic Test - Alkenes

5.5Alcohols

5.5.1Production of Alcohols

5.5.2Oxidation of Alcohols

5.5.3Oxidation of Alcohols - 2

5.5.4Elimination Reactions

5.5.5End of Topic Test - Alcohols

5.5.6Exam-Style Question - Alcohols

5.6Organic Analysis

5.6.1Reactions

5.6.2Reactions 2

5.6.3Mass Spectrometry

5.6.4Infrared Spectroscopy

5.6.5End of Topic Test - Organic Analysis

5.7A-A* (AO3/4) - Organic 1

5.7.1A-A* (AO3/4) - Organic 1

6Organic Chemistry 2 (A2 Only)

6.1Optical Isomerism (A2 Only)

6.1.1Optical Isomerism (A2 Only)

6.1.2End of Topic Test - Optical Isomerism

6.2Aldehydes & Ketones (A2 Only)

6.2.1Aldehydes & Ketones (A2 Only)

6.2.2End of Topic Test - Aldehydes & Ketones

6.3Carboxylic Acids & Esters (A2 Only)

6.3.1Acids & Esters (A2 Only)

6.3.2Acylation (A2 Only)

6.3.3End of Topic Test - Carboxylic Acids & Esters

6.4Aromatic Chemistry (A2 Only)

6.4.1Structure & Reactivity (A2 Only)

6.4.2Reactions of Benzene (A2 Only)

6.4.3End of Topic Test - Aromatic Chemistry

6.5Amines (A2 Only)

6.5.1Nature & Preparation of Amines (A2 Only)

6.5.2Basicity & Nucleophilicity (A2 Only)

6.5.3End of Topic Test - Amines

6.6Polymers (A2 Only)

6.6.1Condensation Polymers (A2 Only)

6.6.2Biodegradability (A2 Only)

6.7Biological Organic (A2 Only)

6.7.1Amino Acids (A2 Only)

6.7.2Proteins (A2 Only)

6.7.3DNA (A2 Only)

6.7.4Anti-Cancer Drugs (A2 Only)

6.7.5End of Topic Test - Biological Organic

6.8Organic Synthesis (A2 Only)

6.8.1Organic Synthesis (A2 Only)

6.8.2Examples of Synthetic Routes (A2 Only)

6.8.3End of Topic Test - Polymers & Organic Synthesis

6.9NMR Spectroscopy (A2 Only)

6.9.1Understanding NMR (A2 Only)

6.9.2Carbon-13 NMR (A2 Only)

6.9.3Hydrogen-1 NMR (A2 Only)

6.9.4Hydrogen-1 NMR 2 (A2 Only)

6.9.5End of Topic Test - NMR

6.10Chromatography (A2 Only)

6.10.1Overview of Chromatography (A2 Only)

6.10.2Thin-Layer Chromatography (A2 Only)

6.10.3Column Chromatography (A2 Only)

6.10.4Gas Chromatography (A2 Only)

6.10.5End of Topic Test - Chromatography

6.11A-A* (AO3/4) - Organic 2

6.11.1A-A* (AO3/4) - Organic 2

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