Chemistry PU2A SFMS 2012 Page 2
: from latin meaning "across" - as intransatlantic).In the other, the two chlorine atoms are locked on thesame side of the double bond. This is known as the
: from latin meaning "on this side")The most likely example of geometric isomerism youwill meet at an introductory level is but-2-ene. In onecase, the CH
groups are on opposite sides of thedouble bond, and in the other case they are on thesame side.
The importance of drawing geometric isomersproperly
It's very easy to miss geometric isomers in exams if you take short-cuts in drawing the structural formulae.For example, it is very tempting to draw but-2-ene asCH
If you write it like this, you will almost certainly missthe fact that there are geometric isomers. If there iseven the slightest hint in a question that isomersmight be involved,
draw compoundscontaining carbon-carbon double bonds showing thecorrect bond angles (120°) around the carbon atomsat the ends of the bond. In other words, use theformat shown in the last diagrams above.
How to recognise the possibility of geometricisomerism
You obviously need to have restricted rotationsomewhere in the molecule. Compounds containing acarbon-carbon double bond have this restrictedrotation. (Other sorts of compounds may haverestricted rotation as well, but we are concentrating onthe case you are most likely to meet when you firstcome across geometric isomers.) If you have acarbon-carbon double bond, you need to thinkcarefully about the possibility of geometric isomers.
What needs to be attached to the carbon-carbon double bond?
Think about this case: Although we've swapped the right-hand groupsaround, these are still the same molecule. To get fromone to the other, all you would have to do is to turnthe whole model over.You
have geometric isomers if there are twogroups the same on one end of the bond - in thiscase, the two pink groups on the left-hand end.So . . . there must be two different groups on the left-hand carbon and two different groups on the right-hand one. The cases we've been exploring earlier arelike this:But you could make things even more different andstill have geometric isomers: