Phenols A phenol has a hydroxyl group bonded directly to a carbon that is part of an aromatic ring.
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
Chemical Properties 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
Lucas Test Used to distinguish between a primary, secondary and tertiary alcohol.
Chromic Acid Test Used to distinguish primary and secondary alcohols from tertiary alcohols. Phenols produce a brown tarry mass when combined with chromic acid.
Iodoform Test This test is used to distinguish alcohols with the partial structure R-CH 3 CH(OH) from other alcohols. Phenols also react.
Acidity of Phenol Phenols are acidic and dissolve in a basic solution. Alcohols are not acidic and will not dissolve in a basic solution.
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.
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!!
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