Reaction Schemes
- A large number of organic products are made from a few starting compounds using appropriate reagents and conditions
- Knowing how organic functional groups are related to each other is key to the synthesis of a given molecule
- 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
- The given molecule is usually called the target molecule and chemists try to design a synthesis as efficiently as possible
- Designing a reaction pathway starts by drawing the structures of the target molecule and the starting molecule
- 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
- 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
Examiner Tip
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