Why is phenol a stronger acid than ethanol, and what do substituents do to acid strength? Then the reactions of alcohols: substitution, dehydration, esterification and oxidation, and the tests that tell the classes apart. The course ends with phenol, including the Kolbe and Reimer-Tiemann reactions.
3 lessons, about 1 h 20 min3 simulations10 problems3 practice questionsPython in every lesson
Alcohols and phenols both lose the hydrogen of OH as a proton, and both are weak acids. Phenol is about a million times stronger than ethanol because its anion spreads the negative charge over the ring. Groups that pull electrons, such as NO, raise the acidity further. Groups that push electrons lower it.
An alcohol can lose its OH (substitution and dehydration), form an ester, or be oxidised. The class of the alcohol decides how fast it reacts with the Lucas reagent, how easily it dehydrates and what the oxidising agent makes. These differences are the basis of the tests that tell primary, secondary and tertiary alcohols apart.
Phenol is made industrially from cumene, and in the laboratory from a diazonium salt or by fusing a sulphonic acid with alkali. Its OH group makes the ring very reactive. Bromine water gives a white tribromophenol at once. The Kolbe and Reimer-Tiemann reactions put a COOH or CHO group at the ortho position.
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