Planning Reaction Schemes (Edexcel IAL Chemistry)
Reaction Schemes
Spec point —
20.3
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A large number of organic products are made from a few starting compounds using appropriate reagents and conditions
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Knowing how organic functional groups are related to each other is key to the synthesis of a given molecule
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The main functional groups you need to know are
- Alkanes
- Alkenes
- Haloalkanes
- Nitriles
- Amines
- Alcohols
- Carbonyls (aldehydes & ketones)
- Hydroxynitriles
- Carboxylic acids
- Esters
- Acyl chlorides
- Primary and secondary amides
Aliphatic Reaction Pathways
- The key interconversions between functional groups are summarised here:
Aliphatic Reactions Table
| Reactant | Product | Reagents | Reaction |
|---|---|---|---|
| Alkene | Haloalkane | X2 / HX | Electrophilic addition |
| Alkene | Alcohol | Steam + H2SO4 / heat | Hydration |
| Alkene | Alkane | Hydrogen + Ni catalyst / 150 oC | Electrophilic addition / hydrogenation |
| Alcohol | Alkene | Al2O3 or conc. H2SO4 / heat | Elimination / dehydration |
| Alcohol | Haloalkane | NaX + H2SO4 / reflux | Nucleophilic substitution |
| Haloalkane | Alcohol | NaOH (aq) / reflux | Nucleophilic substitution |
| Alkane | Haloalkane | Halogen / UV light | Free radical substitution |
| Primary alcohol | Aldehyde | K2Cr2O7 / H2SO4 / distil | Oxidation |
| Secondary alcohol | Ketone | K2Cr2O7 / H2SO4 / Heat | Oxidation |
| Primary alcohol | Carboxylic acid | K2Cr2O7 / H2SO4 / reflux | Oxidation |
| Aldehyde | Primary alcohol | NaBH4 / H2O | Reduction / nucleophilic addition |
| Ketone | Secondary alcohol | NaBH4 / H2O | Reduction / nucleophilic addition |
| Haloalkane | Nitrile | Aqueous ethanolic KCN / Heat | Nucleophilic substitution |
| Halogenoalkane | Amine | NH3 / ethanol | Nucleophilic substitution |
| Nitrile | Carboxylic acid | H2O / HCl | Hydrolysis |
| Aldehyde | Hydroxynitrile | NaCN / H+ | Nuclophilic addition |
| Alcohol | Ester | Carboxylic acid / H2SO4 | Esterification |
| Carboxylic acid | Ester | Alcohol / H2SO4 | Esterification |
| Ester | Carboxylate salt and alcohol | NaOH (aq) | Alkaline hydrolysis |
| Ester | Carboxylic acid | Dilute acid | Acid hydrolysis |
| Carboxylic acid | Acyl chloride | SOCl2 | Chlorination |
| Acyl chloride | Carboxylic acid | H2O | Hydrolysis |
| Acyl chloride | Primary amide | NH3 | Nucleophilic addition elimination |
| Acyl chloride | Secondary amide | Primary amine | Nucleophilic addition elimination |
Aromatic Reaction Pathways
- The key aromatic reactions are summarised here:
Aromatic Reactions Table
| Reactant | Product | Reagents | Reaction |
|---|---|---|---|
| Benzene | Methylbenzene / toluene | CH3Cl / AlCl3 | Alkylation / Electrophilic substitution |
| Benzene | Bromobenzene | Br2 / FeBr3 | Bromination / Electrophilic substitution |
| Benzene | Chlorobenzene | Cl2 / AlCl3 | Chlorination / Electrophilic substitution |
| Benzene | Nitrobenzene | HNO3 / H2SO4 | Nitration / Electrophilic substitution |
| Nitrobenzene | Aminobenzene / phenylamine / aniline | Sn / HCl | Reduction |
| Aminobenzene | 2,4,6-tribromoaminobenzene / 2,4,6-tribromoaniline | Bromine | Electrophilic substitution |
| Benzene | Phenylethanone | CH3COCl / AlCl3 | Acylation / Electrophilic substitution |
| Phenylethanone | 1-phenylethanol | NaBH4 | Reduction |
Designing a Reaction Pathway
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The given molecule is usually called the target molecule and chemists try to design a synthesis as efficiently as possible
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Designing a reaction pathway starts by drawing the structures of the target molecule and the starting molecule
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Determine if they have the same number of carbon atoms
- If you need to lengthen the carbon chain you will need to put on a nitrile group by nucleophilic substitution
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Work out all the compounds that can be made from the starting molecule and all the molecules that can be made into the target molecule
- Match the groups they have in common and work out the reagents and conditions needed
Worked Example Suggest how the following syntheses could be carried out:
a) Chloroethane to ethanoic acid
b) Ethene to 1-aminopropane
Answer 1
Answer 2
Exam Hint You could be required to design a synthesis with up to four steps
Part of this process can include identifying appropriate control measures to reduce risk, based on data about hazards
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