A phenol
is one of a number of chemically active compounds which are found
throughout nature, especially in plants. Their molecules each include a
hydroxyl functional group (OH) bonded to the ring of an aromatic compound
— a molecule that includes at least one ring of carbon atoms. Phenols
exhibit a wide range of properties; some are heralded for their health
benefits, while others are deadly poisons. Some have important
industrial uses as drugs or food additives. The word phenol may also refer to carbolic acid (C6H5OH), the simplest of this group of chemicals.
Phenol
is the simplest member of a family of compounds in which an -OH group
is attached directly to a benzene ring. Phenol itself is the only one of
the family that you are likely to need to know about for UK A level
purposes.
There is an interaction between the delocalised
electrons in the benzene ring and one of the lone pairs on the oxygen
atom. This has an important effect on both the properties of the ring
and of the -OH group.
Pure phenol is a white crystalline solid,
smelling of disinfectant. It has to be handled with great care because
it causes immediate white blistering to the skin. The crystals are often
rather wet and discoloured.
Phenol is so inexpensive that it
attracts many small-scale uses. It once was widely used as an
antiseptic, especially as carbolic soap, from the early 1900s through
the 1970s. It is a component of industrial paint strippers used in the
aviation industry for the removal of epoxy, polyurethane and other
chemically resistant coatings. Phenol derivatives are also used in the
preparation of cosmetics including sunscreens, hair colorings, and skin
lightening preparations. Concentrated phenol liquids are commonly used
in the surgical treatment of ingrown toenails to prevent a section of
the toenail from growing back. This process is called phenolization.
When
phenol donates a hydrogen ion to water, the electron pair remaining on
the oxygen atom becomes delocalized, meaning that it becomes
redistributed into the phenyl ring and cannot be assigned with certainty
to any one pair of atoms. This effect is possible because of the π
bonds in the phenyl ring (bonds that form between overlapping
unhybridized p-orbitals). In cyclohexanol, on the other hand, all of the
carbons in the ring structure share single bonds and there are no π
bonds, so the negative charge on the oxygen does not become delocalized
if the hydrogen is donated to water.
In a phenol extraction, the acidity of the whole mixture is important to effectively extract the DNA and RNA. Chemists recommend that the phenol
should have a pH higher than 7 so that the water layer can successfully
gather the DNA. At a pH of 4.5, which is already considered acidic, the
RNA can already be gathered by the water phase. To change the phenol’s acidity or alkalinity, some chemicals are added, such as the compound tris or N-ethylmorpholine.
Edit by http://www.hiseachem.com
No comments:
Post a Comment