5.6.1
Reactions
Testing Alcohols
Testing Alcohols
We can test alcohols to decide whether they are primary, secondary or tertiary.
The test
The test
- We must warm the alcohol and then add acidified potassium dichromate (V).
- Primary: turns green.
- Secondary: turns green.
- Tertiary: nothing happens.
The problem
The problem
- The issue with this test is that it gives the same result for primary and secondary alcohols.
- A rough way to differentiate between the two is that, generally, primary alcohols will react faster - the green colour will form quicker.
- But this is unreliable.
Overcoming the problem
Overcoming the problem
- A better way to differentiate is by testing the products of the first test.
- In the first test, the acidified potassium dichromate (V) oxidises:
- Primary alcohols to aldehydes.
- Secondary alcohols to ketones.
- So we can carry out an aldehyde/ketone test to determine which alcohol was initially present.
- The aldehyde/ketone test uses either Fehling's solution or Tollen's reagent - it has been covered before.
Aldehyde or Ketone
Aldehyde or Ketone
We can determine whether a chemical is either an aldehyde or a ketone through two possible tests.
Aldehydes and ketones
Aldehydes and ketones
- Aldehydes and ketones have very similar functional groups and so are hard to tell apart.
- The one feature they have that is different is their oxidising ability.
- So we can use oxidising agents to identify which is present.
Oxidising ability
Oxidising ability
- Aldehydes can be oxidised further (twice) to carboxylic acids.
- This is because they still have a C-H bond that can be broken for oxidation.
- Ketones cannot be further oxidised (only once).
- You would have to break a C-C bond.
Fehling's solution
Fehling's solution
- Our first test is Fehling’s solution.
- It contains Cu2+ and is deep blue.
- When you add an aldehyde, the Cu2+ oxidises the aldehyde and is reduced to Cu+.
- This causes a colour change from deep blue to brick red.
- With a ketone, you get no colour change because it can’t be oxidised.
Tollen's reagent
Tollen's reagent
- Tollen’s reagent contains the diamine silver 1+ ion: [Ag(NH3)2]+.
- This is a clear solution.
- This reagent also oxidises an aldehyde, but will do nothing to a ketone.
- When it oxidises an aldehyde, it is reduced to solid silver and is said to form a ‘silver mirror’ on the surface of the test tube.
Overall test results
Overall test results
- Fehling's solution:
- Aldehyde: Deep blue → brick red.
- Ketone: Remains deep blue.
- Tollen's reagent:
- Aldehyde: Clear → silver mirror.
- Ketone: Remains clear.
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
1.3Bonding
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
1.5Kinetics
1.6Equilibria
2Physical Chemistry 2 (A2 Only)
2.1Thermodynamics (A2 Only)
2.2Rate Equations (A2 Only)
2.3The Equilibrium Constant Kp (A2 Only)
2.4Electrochemical Cells (A2 Only)
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
4Inorganic Chemistry 2 (A2 Only)
4.1Period 3 (A2 Only)
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)
5Organic Chemistry 1
5.1Introduction
5.2Alkanes
5.3Halogenoalkanes
5.4Alkenes
5.5Alcohols
5.6Organic Analysis
5.7A-A* (AO3/4) - Organic 1
6Organic Chemistry 2 (A2 Only)
6.1Optical Isomerism (A2 Only)
6.2Aldehydes & Ketones (A2 Only)
6.3Carboxylic Acids & Esters (A2 Only)
6.4Aromatic Chemistry (A2 Only)
6.5Amines (A2 Only)
6.6Polymers (A2 Only)
6.7Biological Organic (A2 Only)
6.8Organic Synthesis (A2 Only)
6.9NMR Spectroscopy (A2 Only)
6.10Chromatography (A2 Only)
6.11A-A* (AO3/4) - Organic 2
Jump to other topics
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
1.3Bonding
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
1.5Kinetics
1.6Equilibria
2Physical Chemistry 2 (A2 Only)
2.1Thermodynamics (A2 Only)
2.2Rate Equations (A2 Only)
2.3The Equilibrium Constant Kp (A2 Only)
2.4Electrochemical Cells (A2 Only)
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
4Inorganic Chemistry 2 (A2 Only)
4.1Period 3 (A2 Only)
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)
5Organic Chemistry 1
5.1Introduction
5.2Alkanes
5.3Halogenoalkanes
5.4Alkenes
5.5Alcohols
5.6Organic Analysis
5.7A-A* (AO3/4) - Organic 1
6Organic Chemistry 2 (A2 Only)
6.1Optical Isomerism (A2 Only)
6.2Aldehydes & Ketones (A2 Only)
6.3Carboxylic Acids & Esters (A2 Only)
6.4Aromatic Chemistry (A2 Only)
6.5Amines (A2 Only)
6.6Polymers (A2 Only)
6.7Biological Organic (A2 Only)
6.8Organic Synthesis (A2 Only)
6.9NMR Spectroscopy (A2 Only)
6.10Chromatography (A2 Only)
6.11A-A* (AO3/4) - Organic 2
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