Classification and Identification of Alcohols and Phenols

Alcohols may be classified as either primary, secondary or tertiary depending on the number of carbon-containing groups attached to the carbon- bearing hydroxyl group. Types of Alcohols

Examples of Alcohols

A phenol has a hydroxyl group bonded directly to a carbon that is part of an aromatic ring. Phenols

Properties of Alcohols and Phenols Alcohols and phenols are polar because of the hydroxyl group The polar side and hydrogen bonding allows them to dissolve in water The non-polar side allows them to dissolve in certain organic solvents Alcohols are not acidic Phenols are acidic Properties of Alcohols and Phenols

A series of tests can be used to distinguish between alcohol types and phenols: Solubility pH Lucas Test Chromic Acid Test Iodoform Test Iron(III)chloride Test Chemical Properties

Used to distinguish between a primary, secondary and tertiary alcohol. Lucas Test

Used to distinguish primary and secondary alcohols from tertiary alcohols. Phenols produce a brown tarry mass when combined with chromic acid. Chromic Acid Test

This test is used to distinguish alcohols with the partial structure R-CH3CH(OH) from other alcohols. Phenols also react. Iodoform Test

Phenols are acidic and dissolve in a basic solution Phenols are acidic and dissolve in a basic solution. Alcohols are not acidic and will not dissolve in a basic solution. Acidity of Phenol

Iron(III) Chloride Test This test distinguishes between alcohols and phenols. The resulting color change can vary from green to purple. Alcohols produce no color change. Iron(III) Chloride Test

Caution! Chromic acid is very corrosive. Phenols are toxic, avoid skin contact. Your instructor will dispense all of the chromic acid as well as police the hazardous waste. DO NOT THROW ANY CHEMICALS DOWN THE DRAIN!!! EACH HAS AN APPROPRIATE WASTE CONTAINER IN THE HOOD!! Caution!

Potential Health Effects Inhalation: difficulty breathing, sore throat, coughing, dizziness, dullness, headache, drowsiness, sneezing, wheezing, central nervous system depression, narcosis, unconsciousness, choking, inflammation of the upper respiratory system, pulmonary edema, circulatory failure, coma, increased sweating, pulmonary edema, reduced body temperature, euphoria, cyanosis, tissue necrosis, convulsion, chemical pneumonitis and death Ingestion: sore throat, narcosis, abdominal pain, nausea, headache, dizziness, diarrhea, kidney damage, liver damage, hearing damage, burns and inflammation of the mouth, throat, esophagus and stomach, brown stains around the mouth, low blood pressure, tachycardia, vomiting , muscular weakness, increased sweating and death Skin contact: sensitization, irritant, redness, pain, drying, cracking, defatting of the skin ulcers, rash and can be absorbed through the skin Eye contact: stinging, tearing, redness, pain of the eyes, blurred vision, corneal damage and blindness Tumorigens, mutagens, carcinogens and reproductive effectors Potential Health Effects