1.

Describe the physical and chemical characteristic of phenol, give

the therapeutic uses and toxic effects of using phenol in the medical
industry.

Physical and Chemical Properties

Phenols are the organic compounds that have a benzene ring bonded to a
hydroxyl group. They are also called as carbolic acids. Phenols are colorless liquids
or crystalline solids but become colored due to slow oxidation with air. They exhibit
unique physical and chemical properties that are mainly due to the presence of a
hydroxyl group.

Phenols generally have higher boiling points in comparison to other hydrocarbons

with equal molecular masses. The main reason behind this is the presence of
intermolecular hydrogen bonding between hydroxyl groups of phenol molecules. In
general, the boiling point of phenols increases with increase in the number of carbon
atoms. The hydroxyl group determines the solubility of phenol in water. The hydroxyl
group in phenol is responsible for the formation of intermolecular hydrogen bonding.
Thus, hydrogen bonds form between water and phenol molecules which make
phenol soluble in water. Phenols react with active metals such as sodium, potassium
etc. and give the corresponding phenoxide. These reactions of phenols indicate its
acidic nature. In phenol, the sp2 hybridized carbon of the benzene ring attached
directly to the hydroxyl group acts as an electron withdrawing group. Thus, it
decreases the electron density of oxygen. Due to the delocalization of negative
charge in the benzene ring, phenoxide ions are more stable than alkoxide ions.
Therefore, we can say phenols are more acidic than alcohols. Electrophilic
substitution reactions, the presence of OH group on benzene increases the
electron density on the benzene ring making it more susceptible to attack by an
electrophile. The reactions involving benzene ring are electrophilic substitution
reaction. The presence of OH group makes the ortho and para carbon of benzene
more electron rich than meta position. The OH group is called o ‒, p ‒ directing
group. Esters of phenol gives phenolic ketones on rearrangement in the presence
of anhydrous AlCl3. This reaction is called fries rearrangement.

Uses of phenol

Phenol is an antiseptic and disinfectant. It is active against a wide range of

micro-organisms including some fungi and viruses, but is only slowly effective
against spores. Phenol has been used to disinfect skin and to relieve itching.
Phenol is also used as an oral analgesic or anesthetic in products such as
Chloraseptic to treat pharyngitis. Additionally, phenol and its related compounds
are used in surgical ingrown toenail treatment, a process termed phenolization.
Research indicates that parental exposure to phenol and its related compounds
are positively associated with spontaneous abortion.

Toxic Effects of Using Phenol

Phenol is toxic with a probable oral lethal dose to humans of 50-500 mg/kg. Some
individuals may be hypersensitive with lethality or serious effects at very low
exposures. Rapid absorption and severe systemic toxicity can occur after any
route of exposure including skin. Death and severe toxicity are usually due to
effects on the CNS, heart, blood vessels, lung, and kidneys. However, toxic
manifestations may vary somewhat with the route. Observed effects from acute
exposure may include: shock, delirium, coma, pulmonary distress, phenolic breath,
scanty/dark urine, and death. Protracted or chronic exposure usually results in
major damage to the liver, kidneys and eyes. Pigmentary changes of the skin have
been noted. Consumption of water contaminated with phenol resulted in diarrhea,
mouth sores, burning of the mouth, and dark urine. Phenol is highly caustic to
tissues. Skin exposure results in pain, then numbness, blanching, severe burns,
and eschar formation. Ingestion leads to burning of throat and severe
gastrointestinal inflammation. Inhalation can result in pulmonary irritation and
edema.

Physical Properties of Alcohol, Phenols and Ethers: Concepts, Video, Q&A. (2019,
September 17). Retrieved from
https://www.toppr.com/guides/chemistry/alcohols-phenols-and-ethers/physical-
properties-of-alcohols-phenols-and-ethers/.

Phenol. (n.d.). Retrieved from https://www.drugbank.ca/drugs/DB03255.

(n.d.). Retrieved from https://toxnet.nlm.nih.gov/cgi-

bin/sis/search/a?dbs+hsdb:@term+@DOCNO+113.