Alcohols
Classifying alcohols
Alcohol homologous series
Physical properties
Reactions of alcohols
-OH functional group (hydroxyl group)
Hydroxyl group: physical/ chemical properties of alcohols
CH3OH (methanol):
high performance fuel (efficient combustion)
Chemical feedstock- starting material in industrial syntheses
Adhesive
Solvent
C2H5OH (ethanol):
alcoholic drinks
Fuel
Solvent
Feedstock
Naming alcohols:
Suffix: -ol
Position of OH functional group
e.g. 2-methylbutan-2,3-diol
Volatility and boiling points: Alcohols have lower volatility than alkanes because:
Liquid: hydrogen bonds hold alcohol molecules together
(must be broken change into gas) more energy required overcome hydrogen bonds than london forces
Water solubility:
Alcohols more water soluble than alkanes because: alkanes are non-polar cannot form hydrogen bonds in H2O
Methanol/ ethanol: soluble in water- hydrogen bonds form between polar O-H group alcohol and H20 molecules
Solubility decreases = carbon atoms increase (influence OH group decreases)
Alkanes: non-polar bonds because electronegativity of hydrogen and carbon are very similar = NON-POLAR (intermolecular forces: LONDON FORCES)
Alcohols: polar O-H bond because difference electronegativity oxygen and hydrogen atoms = POLAR (intermolecular forces: london forces and HYDROGEN BONDS between polar O-H groups
Primary/ Secondary/ Tertiary: number hydrogen atoms and alkyl groups attached carbon atom that contains OH functional group
Primary alcohols:
E.g. methanol/ ethanol
-OH group attached carbon atom attached 2 hydrogen atoms/ 1 alkyl group
Secondary alcohols:
E.g. propan-2-ol/ pentan-3-ol
-OH group attached carbon atom attached 1 hydrogen atom/ 2 alkyl groups
Tertiary alcohols:
E.g. 2-methylpropan-2-ol/ 2-methylbutan-2-ol
-OH group attached carbon atom attached NO hydrogen atoms/ 3 alkyl groups
Combustion of alcohols
React with O2 produce: CO2/ H2O Exothermic reaction: release energy as heat
Carbon atoms increase quantity released per mole increases
Oxidation of alcohols:
Oxidising agent- K2Cr2O7/H2SO4
Color change: orange (Cr2O72-) to green (Cr3+)
Oxidation of primary alcohols:
Aldehydes/ carboxylic acids (aldehydes oxidised to carboxylic acids)
Aldehydes
Gentle heating of primary alcohols with acidified potassium dichromate (VI)
Aldehyde distilled out of reaction mixture (prevents further reaction with oxidising agent)
Dichromate (VI) ions change color orange to green
Carboxylic acids
Primary alcohol heated strongly under reflux with excess acidified potassium dichromate (VI) (excess ensure alcohol oxidised)
Heated under reflux ensure aldehyde formed initially undergoes oxidation to carboxylic acid
Aldehyde: distillation remove aldehyde from reaction mixture
Carboxylic acid: heat alcohol under reflux
Oxidation of secondary alcohols:
Ketones (cannot further oxidise using acidified dichromate (VI) ions
Heated under reflux with acidified dichromate (VI) iions
Dichromate (VI) ions change color orange to green
Suffix: -ONE
Suffix: -AL
Suffix: -OIC ACID
Oxidation of tertiary alcohols:
Do not undergo oxidation reactions
Acidified dichromate (VI) remains orange
Dehydration of alcohols:
Dehydration: reaction which water molecule removed from starting material
Alcohol heated under reflux in presence acid catalyst e.g. conc. H2SO4/ conc. H2PO4
Product: alkene
Elimination reaction
Substitution of alcohols:
Alcohols + hydrogen halides form haloalkanes
Heated under reflux with H2SO4 and sodium halide a hydrogen bromide formed in situ (in place)
HBr reacts alcohol produce haloalkane