14.2 Reactions of Alcohols
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What types of reactions can alcohols undergo?
COMBUSTION OXIDATION SUBSTITUTION DEHYDRATION
What is the general equation for combustion of an alcohol?
Alcohol + Oxygen ⟶ Carbon Dioxide + Water
Under what conditions does combustion occur?
high temperature
Is combustion exothermic or endothermic?
exothermic
Under what condition do alcohols become oxidised?
acidified potassium dichromate solution K2Cr2O7 (aq) + H2SO4 (aq)
What is the oxidising agent in oxidation of alcohols/aldehydes?
acidified potassium dichromate ions
During oxidation, are potassium dichromate ions oxidised or reduced?
reduced
What is the colour change during oxidation of alcohols and the formation of what ion is responsible for this colour change?
orange to green Cr3+
What is the general equation for oxidation of PRIMARY ALCOHOLS?
PARTIAL: Primary alcohol + [O] ⟶ Aldehyde + Water COMPLETE: Primary alcohol + 2[O] ⟶ Carboxylic acid + Water
What organic product is formed when a PRIMARY alcohol undergoes oxidation under GENTLE HEATING + EXCESS ALCOHOL?
aldehyde
What organic product is formed when a PRIMARY alcohol undergoes oxidation under REFLUX + EXCESS OXIDISING AGENT?
carboxylic acid
What conditions are used in PARTIAL OXIDATION of PRIMARY alcohols?
GENTLE HEATING EXCESS ALCOHOL - less complete oxidation (∵ not enough oxidising agent to fully oxidise) ALDEHYDE DISTILLED OUT - prevents further oxidation into carboxylic acid
What conditions are used in COMPLETE OXIDATION of PRIMARY alcohols?
REFLUX EXCESS OXIDISING AGENT - make sure all alcohol molecules fully oxidised
What organic product is formed when a SECONDARY alcohol undergoes oxidation?
ketone
What conditions are used in the oxidation of SECONDARY alcohols?
reflux - ensure reaction is complete
What organic product is formed when a TERTIARY alcohol undergoes oxidation?
TERTIARY ALCOHOLS CANNOT UNDERGO OXIDATION REACTIONS
Under reflux: Primary alcohols oxidise to _____. Secondary alcohols oxidise to _____.
carboxylic acids ketones
What compound can be used as a test for the presence of a carboxylic acid?
METAL CARBONATE CO2 gas released since acid + metal carbonate ⟶ salt + water + carbon dioxide
(Carboxylic) acid + metal carbonate ⟶
salt + water + carbon dioxide
oxidising a primary alcohol ⟶ aldehyde, what is the change in number of hydrogens and oxygens?
loses 2 hydrogens (oxygen added takes these 2 hydrogens to form water) Overall no change in oxygen.
the [O] oxygen being added to alcohols causes the formation of what inorganic molecule? (except aldehyde -> carboxylic acid)
water O takes 2 hydrogens from the alcohol molecule.
What is the general equation for dehydration of an alcohol?
Alcohol ⟶ Alkene + Water
What are the conditions for dehydration of an alcohol?
PHOSPHORIC ACID catalyst, H3PO4 REFLUX
What is a dehydration reaction?
2 hydrogens + 1 oxygen removed from saturated molecule forming unsaturated molecule + water