A

little note on Directors, EWG, EDG, Deactivators &Activators What we need to remember is that a Director, whatever it may be (ortho, para, meta) is located ON the molecule undergoing this EAS reaction Note: when this refers to a/the substituent that is the director it should be located on the molecule undergoing EAS before the carbocation is formed, there can be multiple steps in a synthesis one should consider the directors at all points.
If you want practice with this see number 14 on page 219 of the think book

This substituent (s) on the benzene ring being present directs the incoming electrophile to some position on the nucleophillic benzene that produces the most stable carbocation and therefore the reaction yields the most products with the corresponding arrangement. This is a nice picture depicting the EAS reaction with a good 3D view ( see citation below!)

All activators or electron donating groups are ortho/para directors: Here is an example
this is a good example because it shows how the substituent located on the benzene ring before the EAS reaction or the acceptance of the nucleophile occurs (CH3 determines the positioning (the nitro group is a meta director usually but in this case it acts as the electrophile on the nucleophillic aromatic ring!)

BUT! Not all ortho/para directors are Activators:

Halogens are the exception due to their available electron pairs, which can participate in resonance in the carbocation form Think about it this way, the carbocation stability will overall determine the position, which the incoming electrophile is most likely to take. (This is going to be repeated.) Remember what we always say in class, which ends in consider the carbocation stability this is THAT part where we consider the stability of the carbocation and how this will affect the ratio and arrangement of products Considering this now we can see that although the deactivating groups often (not always) cause carbocation instability in the ortho and para positions, the counter example of the halogens shows us that the deactivating nature of these substitutents is in regards to the nucleophillicty, or likeliness to undergo substitution of the aromatic ring but doesnt always make the formed carbocation unstable so a deactivator or electron withdrawing group, might make EAS more difficult initially but it doesnt mean that the deactivator definitively yields meta products. Lets use the halogens to exemplify this I found this picture at this link

www.uncw.edu/chem/.../Electrophilic%20Aromatic%20SubstitutionA.ppt

 Then lets look at the kinetics of this reaction:

As you can see this deactivator while making it harder for the EAS to happen compared to if the halogen was replaced by an activator or H like on benzene, the ortho para positioning still is preferred due to the stability of the carbocation Another consideration The halogens also provide resonance stabilization Due to the availability of their lone pairs rather than simply inductive stabilization (like a CH3) that some groups might be limited to

The Meta Position

Note: remember that not all deactivators are Meta directors; we must consider how these deactivators or electron withdrawing groups effect the carbocation But for those groups that do cause the Meta position to be more preferable this is why first lets examine this picture:

Why is the Meta position preferable and when

The reason that the Meta position is better for the some of these deactivators or electron withdrawing groups is because these particular EWG or deactivators have a partial or full formal charge on the atom that is directly attached to the aromatic ring. What does this cause? Well this places a resonance contributor of the carbocation form in the ortho/para positions directly adjacent to the positive charge on this group as like charges repel this increases instability and therefore isnt beneficial for the carbocation which is the selfish part as I would call it in this reaction, and therefore the meta position avoids this and is the major product. See the figure above again and apply this concept:

Another perspective (not my words, found this at)

"Instead of looking at the charges in the -complex, look at the approach of the electrophile E+. Resonance structures put a + charge in the ortho and para positions. The + charge hinders the approach of the positively charged E+." - Not my words citation to come, trying to find the link as I downloaded the document
This shows a couple things, the meta position allows us to avoid the formation of the carbocation adjacent to another positive charge and the approach of the electrophile (if positive) is easier as well

Here is a chart of some other groups with similar qualities

All pictures are taken from this tutorial from Rutgers University unless otherwise state this is the site you can download the tutorial about this subject, and all EAS reactions

crab.rutgers.edu/~burke/organic/Ch1 7Su08.doc