1) Introduction

The opposite of chiral is achiral. Achiral objects are superimposable with their mirror images. For example, two pieces of paper are achiral. In contrast, chiral molecules, like our hands, are non superimposable mirror images of each other. Try to line up your left hand perfectly with your right hand, so that the palms are both facing in the same directions. Spend about a minute doing Do you see that they cannot line up exactly? The same thing applies to some molecules this.

A Chiral molecule has a mirror image that cannot line up with it perfectly- the mirror images are non superimposable. The mirror images are called enantiomers. But why are chiral molecules so interesting? A chiral molecule and its enantiomer have the same chemical and physical properties(boiling point, melting point,polarity, density etc...). It turns out that many of our biological molecules such as our DNA, amino acids and sugars, are chiral molecules. It is pretty interesting that our hands seem to serve the same purpose but most people are only able to use one of their hands to write. Similarily this is true with chiral biological molecules and interactions. Just like your left hand will not fit propery in your right glove, one of the enantiomers of a molecule may not work the same way in your body. This must mean that enantiomers have properties that make them unique to their mirror images. One of these properties is that they cannot have a plane of symmetry or an internal mirror plane. So, a chiral molecule cannot be divided in two miror image halves. Another property of chiral molecules is optical activity.

Optical Activity
As mentioned before, chiral molecules are very similar to each other since they have the same components to them. The only thing that obviously differs is their arrangement in space. As a result of this similarity, it is very hard to

distinguish chiral molecules from each other when we try to compare their properties such as boiling points, melting points and densities. However, we can differentiate them by their optical activity. When a plane-polarized light is passed through one of the 2 enantiomers of a chiral molecule that molecule rotates light in a certain direction. When the same plane polarized light is passed through the other enantiomer, that enantionmer rotates light by the same amount but in the opposite If one enantiomer rotates the light counterclockwise, the other would rotate it direction. clockwise.

Because chiral molecules are able to rotate the plane of polarization differently by interacting with the electric field differently, they are said to be optically active. In general molecules that rotate light in differen directions are called optical isomers.

Dextrorotatory (+ enantiomer) rotates the plane polarized light clockwise (when viewing towards the light source) Levorotatory (- enantiomer) rotates the plane polarized light counterclockwise

Circular Dichroism
Another property of chiral molecules is called circular dichroism (CD). This pertains to their differential absorption of left and right circularly polarized light. When left and right circularly polarized light passes through chiral molecules, the absorption coefficients differ so that the change in absorption coefficients does not equal zero.

where A is the difference between absorbance of left circularly polarized (LCP) and right circularly polarized (RCP) light (this is what is usually measured). Where [J] = molar concentration of the sample and l is the path length. The CD signals of chiral molecules can give important information and this information can be used for visible and ultraviolet spectroscopy. Every chiral molecule shows a particular CD spectrum. By looking at the distinctive spectra of molecules such as proteins and DNA, we can obtain useful information about their secondary structures and see how they differ. An example of a CD spectrum comparing the differences between A-DNA and B-DNA.

HUCKELS RULE, GET IT FROM PAGE

722 ORGANIC CHEM BOOK

ILL EFFEC TS OF BTEX TO HUMAN HEALTH AND THE ENVIRONMENT

5)
Benzene, toluene, ethylbenzene, xylenes (as BTEX)
The substance BTEX is a group of chemicals, which is quantified by one analytical method. For details concerning benzene see the substance description for benzene. Toluene, ethylbenzene and xylene, which includes three structurally related isomers are colourless liquids, immiscible with water but miscible with organic solvents. They have a characteristic strong odour and are highly flammable. Use Toluene is primarily used as a solvent and in blending petrol. It is a constituent of crude oil and is also produced during the process of making gasoline and other fuels from crude oil, in making coke from coal, and as a by-product in the manufacture of styrene. It is used in paints, paint thinners, fingernail polish, lacquers, adhesives, and rubber and in some printing and leather tanning processes. It is also used in the production of other chemicals. Ethylbenzene is predominantly used as a chemical intermediate in the manufacture of styrene monomer. It is used as a component of solvents, as a diluent in paints and lacquers and as a solvent in the rubber and chemical industries. Currently, mixed xylenes are primarily used for blending into petrol. The remainder is used in a variety of solvent applications, as well as to produce the individual isomers of xylene. Xylene based solvents are widely used in the paint and printing ink industries, for polyester fibre, film and fabricated items and perfumes, pesticide formulations, pharmaceuticals and adhesives. It is also used for household products such as aerosol paints and lacquers. Xylene is also used as a cleaning agent, and as a thinner for paint and varnishes. Individual isomers of xylene are used in the manufacture of certain plastics. Major emissions Toluene, ethylbenzene and xylenes can enter the environment during manufacture or use of these substances or products containing them. Due to the high volatility of BTEX compounds, emissions are expected to occur principally to air. Impacts on human health and environment Excessive exposure to toluene may impair hearing and cause health effects on the brain (neurological), and the unborn child; while for ethylbenzene the brain, eye, lung and skin are of principal concern. Excessive exposure to xylene isomers may cause health effects on the brain, digestive system, ear, eye, heart, kidney, liver, lung, skin, nose, reproductive system, throat and the unborn child. The BTEX compounds are categorised as Volatile Organic Compounds (VOCs) that may contribute to the formation of ground-level ozone and photochemical smog, which can cause damage to plants and materials as well as pose human health concerns. BTEX compounds are considered harmful to aquatic organisms. Benzene, toluene and ethylbenzene are all priority substances under the Existing Substances Regulation 793/93. Risk Assessment Reports have been completed on toluene and benzene and can be downloaded from http://ecb.jrc.it/existing-chemicals/.