What happens if the original haloalkane has chirality?
• AND what is the optical activity of the product? • If the haloalkane has three different R groups on the carbon of the C-Hal bond, i.e. RR’R”CX, then there are four different groups bonded to the carbon of the C-Hal bond. Therefore the molecule is chiral and can exhibit optical isomerism (non-super imposable mirror image forms). If the initial halogenoalkane is an optical isomer, the stereochemical consequences depend on which mechanism by which the halogenoalkane reacts. The results can be very complex and their full explanation goes beyond this level. However there are two product formation trends. • • (Apologies for repeating diagrams but it helps to appreciate these stereochemical points) • In the SN1 carbocation mechanism (e.g. mechanism 1 above), the three bonds of the R groups of the carbocation formed in step (1), are in a trigonal planar arrangement >C-. This means the nucleophile (e.g. OH- or H2O) can attack the carbocation with equal probability on each side. This results
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- What happens if the original haloalkane has chirality?
