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Resonance and Isomers Activity
Follow the direc�ons below for each of the following structures on a separate piece of paper.
1. Redraw the structure adding in all of the electrons to the O, N and to any atom that has a formal charge. (It also
might be helpful to draw in all of the hydrogen atoms. This will allow you to see how many bonds each of the
carbon atoms already has. Remember none of these elements can exceed the octet rule.
2. Using arrows to show the movement of electrons, draw as many resonance structures as you can. Be sure to
show the formal charge on EACH structure.
3. Circle the most contribu�ng structure. (It might be the star�ng structure.)
Type 1: Atoms with C = O bonds and C = N bonds. When there is a bond like this the pi electrons can move to the more
electronega�ve element. This would be the first structure. It is o�en not a major (or even a minor) contributor, but it is
a good star�ng point and it does help to see these.
b.
a.
d.
c.
e.
Type 2: Vinylic anions (nega�ve charges on atoms next to atoms in a double bond) are another common situa�on that
you may see in structures that leads to resonance. Pay aten�on to how many bonds each atoms has! If they already
have an octet, pi electrons must move to allow the lone pair from the nega�ve charge to make a new pi bond.
f.
g.
Type 3: Vinylic ca�ons are similar to the type above, but these usually mean that they are missing electrons, so nearby pi
electrons can move toward these.
h.
j.
i.
k.
Type 4: Vinylic lone pairs are similar to the vinylic anions. Move the lone pairs in and the double bond will become a
lone pair on a different atom.
m.
n.
l.
Use any of the types above to draw at least 4 different resonance structures for the following molecule.
Isomers are compounds that have the same molecular formula but a different bonding patern. Some�mes it can be
difficult to tell if a compound is an isomer or not. Here is some prac�ce. Determine if each pair of compounds are
iden�cal, Isomers, or neither (different formula).
a.
b.
c.
d.
e.
f.
g.
h.
i.
j.
k.
l.
m.
Chemical Structure
Chemical Structure
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