5.5.2

Oxidation of Alcohols

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Ketones and Aldehydes

Ketones and aldehydes are functional groups that can be produced by the oxidation of alcohols.

Ketones

Ketones

  • When you oxidise a secondary alcohol, the molecule you get is called a ketone.
    • Ketones have a carbon double bonded to an oxygen atom, and two other single carbon-carbon bonds.
    • The simplest ketone, propanone (acetone), is shown here.
Naming ketones

Naming ketones

  • We use the general name:
    • Alkan-X-one:
      • Propanone.
      • Butanone.
      • Pentan-2-one or pentan-3-one.
  • The numbers are used on longer alkanes to show on which carbon the ketone group lies.
Aldehydes

Aldehydes

  • You can oxidise a primary alcohol to an aldehyde.
    • An aldehyde has a carbon-oxygen double bond and at least one carbon-hydrogen bond.
    • The simplest aldehyde, methanal (formaldehyde), is shown here.
Naming aldehydes

Naming aldehydes

  • We use the general name:
    • Alkanal:
      • Propanal.
      • Butanal.
      • Pentanal.
  • Here, there is no need for any numbers as the aldehyde group must lie on one of the end carbons.
Carboxylic acids

Carboxylic acids

  • You can oxidise an aldehyde to a carboxylic acid.
    • You cannot oxidise a ketone to a carboxylic acid.
    • The simplest acid, methanoic acid (formic acid), is shown here.

Oxidation of Alcohols

There are different kinds of alcohols, and as always in chemistry, they all have slightly different reactions.

Oxidation

Oxidation

  • Each of the kinds of alcohol can be oxidised to different extents.
  • The rule is that you can break carbon-hydrogen bonds, but not a carbon-carbon bond.
    • Primary alcohols can be oxidised twice.
    • Secondary alcohols can be oxidised once.
    • Tertiary alcohols cannot be oxidised.
  • The usual oxidising agent, for all, is acidified potassium dichromate(VI).
Primary alcohols

Primary alcohols

  • Two possible oxidation reactions for primary alcohols:
    • They can be oxidised to aldehydes.
    • If you change the experimental conditions, you can also oxidise them to carboxylic acids.
Secondary alcohols

Secondary alcohols

  • One possible oxidation reaction for secondary alcohols:
    • You can oxidise them to a ketone.
      • You cannot oxidise it further without breaking carbon-carbon bonds.
Tertiary alcohols

Tertiary alcohols

  • You can’t oxidise a tertiary alcohol at all!
    • Tertiary alcohols have three carbon groups bonded to the alcohol carbon.
    • The only way to add more oxygen involves breaking carbon-carbon bonds.
Jump to other topics
1

Physical Chemistry

1.1

Atomic Structure

1.1.1Fundamental Particles1.1.2Isotopes & Mass Number1.1.3Mass Spectrometry1.1.4Electron Shells, Sub-Shells & Orbitals1.1.5Electron Configuration1.1.6Ionisation Energy1.1.7Factors Affecting Ionisation Energies1.1.8Trends of Ionisation1.1.9Specific Impacts on Ionisation Energies1.1.10End of Topic Test - Atomic Structure1.1.11A-A* (AO3/4) - Atomic Structure
1.2

Amount of Substance

1.2.1Relative Masses1.2.2The Mole1.2.3The Ideal Gas Equation1.2.4Empirical & Molecular Formulae1.2.5Balanced Equations1.2.6Percentage Yield1.2.7A-A* (AO3/4) - Percentage Yield1.2.8Atom Economy1.2.9End of Topic Test - Amount of Substance1.2.10A-A* (AO3/4) - Substances & Yield1.2.11Diagnostic Misconceptions - Moles
1.3

Bonding

1.3.1Ionic Bonding1.3.2Covalent & Dative Bonding1.3.3Carbon Structures1.3.4Metallic Bonding1.3.5Physical Properties1.3.6Shapes of Molecules1.3.7Polarity1.3.8Intermolecular Forces1.3.9Intermolecular Forces 21.3.10End of Topic Test - Bonding1.3.11Exam-Style Question - Shape of Molecules1.3.12A-A* (AO3/4) - Bonding1.3.13Diagnostic Misconceptions - Ions1.3.14Diagnostic Misconceptions - Ionic & Covalent1.3.15Diagnostic Misconceptions - Phase Change1.3.16Diagnostic Misconceptions - Boiling1.3.17Diagnostic Misconceptions - Polar Bonds
1.4

Energetics

1.4.1Enthalpy Changes1.4.2Bond Breaking and Making1.4.3Enthalpy Changes: Standard Conditions1.4.4Calorimetry1.4.5Hess' Law1.4.6Bond Enthalpies1.4.7End of Topic Test - Energetics1.4.8Diagnostic Misconceptions - Calorimetry
1.5

Kinetics

1.5.1Collision Theory1.5.2Maxwell-Boltzmann Distribution1.5.3Increasing Rates1.5.4End of Topic Test - Kinetics
1.6

Equilibria

1.6.1Le Chatelier1.6.2Equilibrium Constants1.6.3A-A* (AO3/4) - Energetics, Kinetics, Equilibria1.6.4End of Topic Test - Equilibria1.6.5Diagnostic Misconceptions - Solids
1.7

Redox

1.7.1Redox1.7.2End of Topic Test - Redox
2

Physical Chemistry 2 (A2 Only)

2.1

Thermodynamics (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 - Thermodynamics2.1.6A-A* (AO3/4) - Thermodynamics
2.2

Rate 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 Equations2.2.6Exam-Style Question - Rates2.2.7A-A* (AO3/4) - Rate Equations
2.3

The Equilibrium Constant Kp (A2 Only)

2.3.1Properties of Kp (A2 Only)
2.4

Electrochemical 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 & Electrochemistry2.4.5A-A* (AO3/4) - Electrochemical Cells2.4.6Diagnostic Misconceptions - Salt Bridges2.4.7Diagnostic Misconceptions - Electrode, Electrolyte
2.5

Acids & 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 & Bases2.5.9Exam-Style Question - Weak Acids2.5.10A-A* (AO3/4) - Acids & Bases2.5.11Diagnostic Misconceptions - Ammonia is an Alkali2.5.12Diagnostic Misconceptions - Water's Neutrality2.5.13Diagnostic Misconceptions - Concentrate & Strength
3

Inorganic Chemistry

3.1

Periodicity & Trends

3.1.1The Periodic Table3.1.2Trends in the Periodic Table3.1.3End of Topic Test - Periodicity & Trends3.1.4Diagnostic Misconceptions - Atomic Radius
3.2

Group 2

3.2.1Group 2 Chemistry3.2.2End of Topic Test - Group 2
3.3

Group 7

3.3.1Introduction to Halogens3.3.2Reactions of Halogens3.3.3Chlorine & Chlorate(I)3.3.4End of Topic Test - Group 73.3.5Exam-Style Question - Group 73.3.6A-A* (AO3/4) - Periodicity, Group 2 & 7
4

Inorganic Chemistry 2 (A2 Only)

4.1

Period 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
4.2

Transition 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 Metals4.2.10A-A* (AO3/4) - Transition Metals
4.3

Reactions 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
5

Organic Chemistry 1

5.1

Introduction

5.1.1Naming Conventions5.1.2Mechanism5.1.3Isomerism5.1.4End of Topic Test - Introduction to Organic Chem
5.2

Alkanes

5.2.1Fractional Distillation5.2.2Cracking5.2.3Combustion5.2.4Chlorination5.2.5End of Topic Test - Alkanes
5.3

Halogenoalkanes

5.3.1Substitution Reactions5.3.2Elimination Reactions5.3.3Ozone Depletion5.3.4End of Topic Test - Halogenoalkanes
5.4

Alkenes

5.4.1Introduction to Alkenes5.4.2Reactions of Alkenes5.4.3Polymerisation Reactions5.4.4Properties of Polymers5.4.5End of Topic Test - Alkenes
5.5

Alcohols

5.5.1Production of Alcohols5.5.2Oxidation of Alcohols5.5.3Oxidation of Alcohols - 25.5.4Elimination Reactions5.5.5End of Topic Test - Alcohols5.5.6Exam-Style Question - Alcohols
5.6

Organic Analysis

5.6.1Reactions5.6.2Reactions 25.6.3Mass Spectrometry5.6.4Infrared Spectroscopy5.6.5End of Topic Test - Organic Analysis
5.7

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

5.7.1A-A* (AO3/4) - Organic 1
6

Organic Chemistry 2 (A2 Only)

6.1

Optical Isomerism (A2 Only)

6.1.1Optical Isomerism (A2 Only)6.1.2End of Topic Test - Optical Isomerism
6.2

Aldehydes & Ketones (A2 Only)

6.2.1Aldehydes & Ketones (A2 Only)6.2.2End of Topic Test - Aldehydes & Ketones
6.3

Carboxylic Acids & Esters (A2 Only)

6.3.1Acids & Esters (A2 Only)6.3.2Acylation (A2 Only)6.3.3End of Topic Test - Carboxylic Acids & Esters
6.4

Aromatic Chemistry (A2 Only)

6.4.1Structure & Reactivity (A2 Only)6.4.2Reactions of Benzene (A2 Only)6.4.3End of Topic Test - Aromatic Chemistry
6.5

Amines (A2 Only)

6.5.1Nature & Preparation of Amines (A2 Only)6.5.2Basicity & Nucleophilicity (A2 Only)6.5.3End of Topic Test - Amines
6.6

Polymers (A2 Only)

6.6.1Condensation Polymers (A2 Only)6.6.2Biodegradability (A2 Only)
6.7

Biological 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
6.8

Organic 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
6.9

NMR 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
6.10

Chromatography (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
6.11

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

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

Practice questions on Oxidation of Alcohols

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  1. 1
    What is the molecule CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>COCH<sub>3</sub> called?Multiple choice
  2. 2
    What type of alcohol is oxidised to form an aldehyde?Multiple choice
  3. 3
    Which of the following can be oxidised to a carboxylic acid?Multiple choice
  4. 4
    How many oxidations can a secondary alcohol undergo?Multiple choice
  5. 5
    An aldehyde comes from the oxidation of which of the following?Multiple choice
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Production of Alcohols

Oxidation of Alcohols - 2