Electrophilic Addition of Alkenes

Alkenes

Alkenes are molecules with a double covalent bond. There is a high electron density between the carbon atoms because of the double bond.

Reactions of alkenes

Alkenes react with several reagents in addition reactions.
The alkenes are nucleophiles because of the high electron density between the carbon atoms.
The mechanism is shown next for the reaction with hydrogen bromide.
The mechanism is called the electrophilic addition mechanism (because an electrophile is added).
They will react in a similar way with sulfuric acid, and bromine.

Electrophilic addition

Above shows the reaction with HBr.

It's the same mechanism for sulfuric acid

With bromine

The reaction can also be done with Br₂.
The partial charges are assigned to the bromine atoms because the high electron density of the double bond repels the bonding electrons and polarises the bond - this is shown in the mechanism.

Uses of Electrophilic Addition

Electrophilic addition reactions between alkenes and bromine as well as alkenes and sulfuric acid are useful.

With bromine

The reaction with bromine is used as a test for alkenes.
- Bromine water is a light orange colour and will be decolourised in the presence of an alkene (light orange → colourless).
This test works because bromine can add to alkenes via an electrophilic addition reaction.

With sulfuric acid

The reaction with sulfuric acid is used to produce alcohols.
- The sulfate ion is removed by nucleophilic substitution.

Asymmetric Electrophilic Addition

Asymmetric alkenes can have multiple products in electrophilic addition reactions.

Multiple products

If you have an asymmetric alkene, you can get multiple products.
- A reaction will favour one of the products over the other - we call this selectivity.
This is shown for the reaction of propene with HBr.

Intermediate stability

This selectivity is driven by carbocation intermediate stability:
- Tertiary carbocations > secondary carbocations > primary carbocations.
The more alkyl groups there are next to the positive charge, the more stable the intermediate is.
- Alkyl groups push electrons and so help to stabilise adjacent positive charge.

Which product when?

When considering which product is most likely, we must consider the intermediates formed.
2-bromopropane is the most likely product because the intermediate is a secondary carbocation, rather than a primary carbocation.
- This is because the secondary carbocation is more stable.
  - It has more alkyl groups pushing electrons onto the positive charge.
Both reactions will happen and you will get both products, but you will have one major and one minor.

1Principles of Science I

1.1Structure & Bonding

1.1.1Atomic Model

1.1.2Electron Shells, Sub-Shells & Orbitals

1.1.3Ionic Bonding

1.1.4Representing Ionic Bonds

1.1.5Covalent Bonding

1.1.6Representing Covalent Bonds

1.1.7Metallic Bonding

1.1.8Intermolecular Forces

1.1.9Intermolecular Forces 2

1.1.10End of Topic Test - Bonding

1.1.11Relative Masses

1.1.12The Mole

1.1.13Molar Calculations

1.1.14Molar Calculations 2

1.1.15Empirical & Molecular Formulae

1.1.16Balanced Equations

1.1.17Percentage Yield

1.1.18End of Topic Test - Amount of Substance

1.2Properties of Substances

1.2.1The Periodic Table

1.2.2Ionisation Energy

1.2.3Factors Affecting Ionisation Energies

1.2.4Trends of Ionisation

1.2.5Trends in the Periodic Table

1.2.6Polarity

1.2.7Metals & Non-Metals

1.2.8Alkali Metals

1.2.9Alkaline Earth Metals

1.2.10Reactivity of Alkaline Earth Metals

1.2.11Redox

1.2.12Transition Metals

1.2.13Redox Reactions of Transition Metals

1.3Cell Structure & Function

1.3.1Introduction to Cells

1.3.2Prokaryotes

1.3.3Organelles of Eukaryotic Cells

1.3.4Organelles of Eukaryotic Cells 2

1.3.5Organelles in Plant Cells

1.3.6Microscopy

1.3.7End of Topic Test - Cell Structure

1.4Cell Specialisation

1.4.1Cell Specialisation

1.4.2Blood Cells

1.4.3Plant Cells

1.4.4Gametes

1.5Tissue Structure & Function

1.5.1Human Gas Exchange

1.5.2Blood Vessels

1.5.3Atherosclerosis

1.5.4Skeletal Muscle

1.5.5Slow & Fast Twitch Fibres

1.5.6Neurones

1.5.7Speed of Transmission

1.5.8Action Potentials

1.5.9End of Topic Test - Neurones & Action Potentials

1.5.10Synapses

1.5.11Types of Synapse

1.5.12Medical Application

1.5.13End of Topic Test - Synapses

1.5.14Chemical Brain Imbalances

1.5.15Effect of Drugs on the Brain

1.6Working with Waves

1.6.1Progressive Waves

1.6.2Wave Speed & Phase Difference

1.6.3Longitudinal & Transverse Waves

1.6.4Stationary Waves

1.6.5Stationary Waves 2

1.6.6Applications of Stationary Waves

1.6.7Interference

1.6.8Diffraction

1.6.9Diffraction Gratings

1.6.10Application of Diffraction Gratings

1.7Waves in Communication

1.7.1Refraction at a Plane Surface

1.7.2Internal Reflection & Fibre Optics

1.7.3Applications of Total Internal Reflection

1.7.4Properties

1.7.5Gamma, X-Ray & UV Light

1.7.6Visible Light

1.7.7Infrared, Microwave & Radio Waves

1.7.8Intensity

1.7.9Digital & Analogue Signals

1.7.10Communication Channels

2Practical Scientific Procedures and Techniques

2.1Titration

2.1.1pH Curves & Titrations

2.1.2pH Curves & Titrations 2

2.1.3Buffer Solutions

2.2Colorimetry

2.2.1Measuring Rates

2.2.2Beer-Lambert Law

2.3Chromatography

2.3.1Overview of Chromatography

2.3.2Thin-Layer Chromatography

2.3.3Column Chromatography

2.3.4Gas Chromatography

3Science Investigation Skills

3.1Scientific Processes

3.1.1Aims, Hypotheses & Sampling

3.1.2Pilot Studies & Design

3.1.3Ethics

3.1.4Variables & Control

3.1.5Demand Characteristics & Investigator Effects

3.1.6Features of Science

3.1.7Scientific Report

3.1.8Scientific Report 2

3.2Data Handling & Analysis

3.2.1Types of Data

3.2.2Descriptive Statistics

3.2.3Presentation & Display of Data

3.3Enzymes in Action

3.3.1Overview of Protein Structure

3.3.2Enzymes

3.3.3Factors Affecting Enzyme Activity

3.3.4Enzyme-Controlled Reactions

3.4Diffusion

3.4.1Diffusion

3.5Plants & Their Environment

3.5.1Factors Affecting Plant Growth

3.5.2Measuring Number & Distribution of Species

3.6Energy Content in Fuels

3.6.1Fractions

3.6.2Burning Hydrocarbons

3.6.3Combustion

3.6.4Energy

3.6.5Energy at Home

3.6.6Calorimetry

3.7Electrical Circuits

3.7.1Circuit Diagrams & Components

3.7.2Diodes, LDRs & Thermistors

3.7.3Resistance

3.7.4Electrical Work

3.7.5Ohm's Law

3.7.6Domestic Uses of Electricity

3.7.7Fuses

4Principles of Science II

4.1Extracting Elements

4.1.1Atom Economy

4.2Relating Properties to use of Substances

4.2.1Group 2 Chemistry

4.2.2End of Topic Test - Group 2

4.2.3Electrolysis

4.2.4Electrolysis Examples

4.2.5Extracting Metals

4.2.6Transition Metals

4.2.7Variable Oxidation States

4.2.8Heterogeneous Catalysts

4.2.9Homogeneous Catalysts

4.3Organic Chemistry

4.3.1Naming Compounds

4.3.2Functional Groups

4.3.3Isomerism

4.3.4Hydrocarbons

4.3.5Structure of Alkanes

4.3.6Boiling Points of Alkanes

4.3.7Alkenes

4.3.8Curly Arrows & Mechanisms

4.3.9Cracking

4.3.10Combustion

4.3.11Free Radical Substitution of Alkanes

4.3.12Electrophilic Addition of Alkenes

4.4Energy Changes in Industry

4.4.1The Kelvin Scale

4.4.2Enthalpy Changes

4.4.3Calorimetry

4.4.4Bond Enthalpies

4.4.5Hess' Law

4.5The Circulatory System

4.5.1The Circulatory System

4.5.2Blood Vessels

4.5.3Blood Transfusion & the ABO Rhesus System

4.5.4The Heart

4.5.5The Cardiac Cycle

4.5.6Cardiac Output

4.5.7Coordination of Heart Action

4.5.8Heart Dissection

4.5.9Controlling Heart Rate

4.5.10Electrocardiograms

4.5.11Cardiovascular Disease

4.5.12Investigating Heart Rates

4.6Ventilation & Gas Exchange

4.6.1Human Gas Exchange

4.6.2Ventilation

4.6.3Measuring Gas Exchange

4.6.4Controlling Ventilation Rate

4.6.5Lung Disease

4.6.6Lung Disease Data

4.7Urinary System

4.7.1Kidneys & Control of Water Balance

4.7.2Kidneys & Osmoregulation

4.7.3Kidneys & Blood Pressure

4.7.4Urine

4.7.5Kidney Failure & Urinalysis

4.7.6Dialysis

4.7.7Transplants

4.8Cell Transport

4.8.1Cell Membrane Structure

4.8.2Diffusion

4.8.3Osmosis

4.8.4Active Transport

4.9Thermal Physics

4.9.1Power & Efficiency

4.9.2Work & Energy

4.9.3Conservation of Energy

4.9.4Pressure

4.9.5First Law of Thermodynamics

4.9.6Second Law of Thermodynamics

4.9.7Heat Engines, Heat Pumps & Refrigerators

4.9.8Non-Flow Processes

4.9.9p-V Diagrams

4.9.10Ideal Gases

4.9.11Ideal Gases 2

4.9.12Thermal Energy Transfer

4.9.13Thermal Energy Transfer Experiments

4.10Materials

4.10.1Density

4.10.2Stress & Strain

4.10.3Properties of Materials

4.10.4Elasticity

4.10.5Plasticity

4.10.6Energy in Materials

4.10.7Young Modulus

4.11Fluids

4.11.1Fluid Flow

4.11.2Viscosity

4.11.3Density

4.11.4Continuity Equation

4.11.5Bernoulli's Equation

4.11.6Non-Newtonian Fluids

5Contemporary Issues in Science

5.1Contemporary Issues in Science

5.1.1Sustainability

5.1.2Genetic Engineering

5.1.3Uses of Genetic Modification

5.1.4Stem Cell Therapy

5.1.5Cloning

5.1.6Cloning 2

5.1.7Nanotechnology

5.1.8Ecosystems

5.2Analysing Scientific Information

5.2.1Validity

5.2.2Peer Review

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