handedness in Molecules

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Presentation transcript:

handedness in Molecules 7.4 CHIRALITY: handedness in Molecules Many molecules exist in “right-handed” and “left-handed forms

Mirror Images

A MIRROR IMAGE IS A REFLECTION

Your left hand is a “mirror image” of your right hand

Some mirror images are ‘superimposable’

Some mirror images are not superimposable (‘nonsuperimposable’) Nonsuperimposable mirror images have ‘right –handed’ and ‘left-handed’ forms… stereoisomers.

Molecules have mirror images too.

‘kye-rality’ like reality Chirality Pronounced ‘kye-rality’ like reality

IN A MOLECULE… a “chiral center” A carbon that is tetrahedral (sp3) and has four different groups attached is called... a “chiral center”

Another name is …. stereocenter H F Cl Br

A molecule with one stereocenter is ‘chiral’. B r F H C l

It’s mirror images are not superimposable F H C l C l H B r F rotate H F B r C l this molecule is chiral non-superimposable mirror images note that the fluorine and bromine are interchanged in the mirror image do interchanges in class

Practice with models Make a molecule with a stereocenter Make it’s mirror image Try to superimpose them Are they the same or different molecules? Interchange two of the atoms. Now try to superimpose them.

PLANES OF SYMMETRY

A SYMMETRIC OBJECT HAS A PLANE OF SYMMETRY - ALSO CALLED A MIRROR PLANE plane of symmetry mirror plane

IF AN OBJECT HAS A PLANE OF SYMMETRY, ITS MIRROR IMAGE WILL BE IDENTICAL

IDENTICAL MIRROR IMAGES WILL SUPERIMPOSE (MATCH EXACTLY WHEN PLACED ON TOP OF EACH OTHER) IF AN OBJECT HAS AN IDENTICAL MIRROR IMAGE IT’S………. ‘ACHIRAL’

CHIRAL An object without symmetry is no symmetry The mirror image of a chiral object is different and will not superimpose on the original object.

WHICH OBJECTS ARE SYMMETRIC ? WHICH OBJECTS ARE ACHIRAL ? (mirror image is identical) sym (outside) achiral achiral sym achiral sym achiral sym

F F C l C l B r B r C l C l ACHIRAL TWO IDENTICAL GROUPS RENDERS A The plane of the paper is a plane of symmetry F F C l C l B r B r C l C l TWO IDENTICAL GROUPS RENDERS A TETRAHEDRAL CARBON ACHIRAL

F F C l C l B r C l B r C l TWO VIEWS OF THE PLANE OF SYMMETRY side view edge view

ACHIRAL A CARBON ATOM WITH THREE SIMILAR GROUPS IS ALSO ACHIRAL ….. Cl Br

plane of symmetry C l C l C l C l B r C l B r C l side view edge view

The whole secret of the study of nature lies in learning how to use ones eye. George Sand, author