Organic Synthesis (AQA A Level Chemistry): Revision Note

Exam code: 7405

Stewart Hird

Written by: Stewart Hird

Reviewed by: Philippa Platt

Updated on

Organic synthesis

  • A wide range of organic products can be made from just a few starting compounds, given the right reagents and conditions

  • Understanding how different organic functional groups interconvert is key to designing synthetic routes

  • The main functional groups you need to know are:

    • Alkanes

    • Alkenes

    • Halogenoalkanes

    • Alcohols

    • Carbonyls (aldehydes & ketones)

    • Carboxylic acids and derivatives

    • Amines

    • Nitriles

    • Arenes

Aliphatic reaction pathways

  • The key transformations between these functional groups are summarised in the diagram and table below:

Flowchart of organic chemistry reactions showing conversions between alkanes, haloalkanes, alcohols, ketones, carboxylic acids, esters, and more.
Main reaction pathways in aliphatic chemistry

Aliphatic reactions table

Reaction

Reagent

Conditions

Mechanism

Reaction type

1

Halogen

UV light

Free radical

Substitution

2

Conc. NH3

Heat, under pressure

Nucleophilic

Substitution

3

Dilute HCl

Room temperature

Acid–base

4

Halogenoalkane

Heat

Nucleophilic

Substitution

5

Halogenoalkane

Heat

Nucleophilic

Substitution

6

Halogenoalkane

Heat

Nucleophilic

Substitution

7

NaOH in ethanol

Heat

Elimination

Elimination

8

Hydrogen halide

Room temperature

Electrophilic

Addition

9

NaOH (aq)

Heat under reflux

Nucleophilic

Substitution

10

KCN in ethanol

Heat under reflux

Nucleophilic

Substitution

11

LiAlH4 in dry ether

Heat

Reduction

12

Halogen

Room temperature

Electrophilic

Addition

13

Steam + H2SO4

Heat

Hydration

14

Al2O3 or Conc. acid

Heat

Elimination

Dehydration / Elimination

15

NaOH (aq)

Heat under reflux

Nucleophilic

Substitution

16

K2Cr2O7 / H2SO4

Heat

Oxidation

17

NaBH4 (aq)

Heat

Reduction

18

K2Cr2O7 / H2SO4

Heat

Oxidation

19

NaBH4 (aq)

Heat

Reduction

20

Dilute HCl

Heat

Hydrolysis

21

K2Cr2O7 / H2SO4

Heat under reflux

Oxidation

22

LiAlH4 in dry ether

Heat

Reduction

23

Alcohol, H2SO4

Heat

Esterification / Condensation

24

Alcohol

Room temperature

Nucleophilic

Addition–elimination / Acylation

25

NaOH (aq)

Room temperature

Acid–base

26

H2O

Room temperature

Hydrolysis

27

Amines

Room temperature

Nucleophilic

Addition–elimination / Acylation

Aromatic reaction pathways

  • The most important reactions of aromatic compounds are summarised below:

Chemical reaction flowchart showing transformations starting from benzene, with intermediates like benzaldehyde, nitrobenzene, and final products like azo dye.
Key reaction pathways in aromatic chemistry

Aromatic reactions table

Reaction

Reagent

Conditions

Mechanism

Reaction Type

1

Ethanoyl chloride + AlCl3

Heat

Electrophilic

Substitution

2

Chloroethane + AlCl3

Heat

Electrophilic

Substitution

3

Chlorine

UV

Free radical

Substitution

4

Chloromethane + AlCl3

Heat

Electrophilic

Substitution

5

Conc. HNO3 + H2SO4

25–60°C

Electrophilic

Substitution

6

Conc. HNO3 + H2SO4

25–60°C

Electrophilic

Substitution

7

Sn + conc. HCl

Heat

Reduction

8

NaNO2 / HCl

Below 10°C

Diazotisation

9

Phenol

Heat

Coupling

Choosing a reaction pathway

  • Chemists often have several possible ways to make a target molecule

    • The best route balances efficiency, safety, and sustainability

Diagram illustrating the twelve principles of green chemistry, including accident prevention, waste prevention, atom economy, less hazardous synthesis.
The twelve principles of green chemistry
  • Choosing a route with fewer steps reduces waste and energy use

    • This is better for the environment and more cost-effective

  • Reactions with high atom economy are preferred

    • They maximise the use of starting materials

  • Safer solvents and less hazardous reagents are also key considerations

Designing a reaction pathway

  • Designing a reaction pathway involves planning a sequence of reactions to convert a starting molecule into a target molecule

  • Synthetic routes are designed to form this compound as efficiently as possible from the given starting material

  • Begin by drawing the structures of both the starting molecule and the target molecule

  • Compare the number of carbon atoms in each compound

    • If the target molecule contains more carbon atoms, the carbon chain may need to be extended

    • One method is to introduce a nitrile group (–CN) via nucleophilic substitution, which increases the carbon chain length by one carbon atom

  • Next, identify the functional groups present in the starting compound and determine which reactions it can undergo

    • Then consider which functional groups are present in the target molecule and how they can be formed

  • Look for possible intermediate compounds that could link the starting material to the target molecule

    • Match functional groups carefully and specify the appropriate reagents and conditions for each step in the pathway

Examiner Tips and Tricks

You could be asked to design a synthesis with up to four steps.

Worked Example

Suggest how the following syntheses could be carried out:

  1. Chloroethane to ethanoic acid

  2. Ethene to 1-aminopropane

Answer 1:

Chemical reaction pathway from CH3CH2Cl to CH3COOH via CH3CH2OH using NaOH and K2Cr2O7 with H2SO4 under heat and reflux.

 

Answer 2:

Chemical reaction pathway from ethene to propylamine, involving reactions with HCl, KCN, and LiAlH4, highlighting intermediate compounds and conditions.

Examiner Tips and Tricks

Being able to combine these reactions in multi-step syntheses is a key exam skill. Practise working backwards from target molecules

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Stewart Hird

Author: Stewart Hird

Expertise: Chemistry Content Creator

Stewart has been an enthusiastic GCSE, IGCSE, A Level and IB teacher for more than 30 years in the UK as well as overseas, and has also been an examiner for IB and A Level. As a long-standing Head of Science, Stewart brings a wealth of experience to creating Topic Questions and revision materials for Save My Exams. Stewart specialises in Chemistry, but has also taught Physics and Environmental Systems and Societies.

Philippa Platt

Reviewer: Philippa Platt

Expertise: Chemistry Content Creator

Philippa has worked as a GCSE and A level chemistry teacher and tutor for over thirteen years. She studied chemistry and sport science at Loughborough University graduating in 2007 having also completed her PGCE in science. Throughout her time as a teacher she was incharge of a boarding house for five years and coached many teams in a variety of sports. When not producing resources with the chemistry team, Philippa enjoys being active outside with her young family and is a very keen gardener