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Ch 5.3 multiple bonds and delocalization

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our next section of of

our studies is going to be the origins

of multi-bonds and you saw a quick

preview of this but it's worth mentioning

mentioning

again so let's take a look at this

ethene molecule where we have a c double bonded

bonded

c on here so we already know based on

our v

valence bond theory that we should have

a sigma bond and

a pi bond and now that we have hybridization

hybridization

we can say that the hybridization for

the carbon atom

has three electron domains so you need

three atomic orbitals to actually form

the hybridization

so both of these carbon atoms are going

to be sp2

hybridized carbon atoms

and as a reminder where did these sp

hybridize orbitals

so we look at the 2p orbitals remember

we can only form hybrid orbitals from

the valence electrons

on here so you have your 2s your 2p we took

took

these three to hybridize to form

our sp2 hybridized orbital

and we're left over here with another p orbital

orbital

so that p orbital remember our pi

bonds are usually formed by p orbitals

so this actually forms

our pi bond on here

so each one of those carbons

has a p orbital

the atomic orbitals or above the bonds

that can form some sort of bonding

kind of interaction on here

so as a reminder your sp2 hybridized orbitals

orbitals

so your sp2 form

all of your sigma bonds on here

and then your pi bonds are formed by the leftover

leftover

p orbitals in the carbon atom

and that can be extended to the triple bond

bond

so we go back to this kind of molecule

over here that we saw earlier we have sp

hybridized so what we did with that sp

is we took

our 2p orbitals and our 2s and we took

these two and find

the uh these

sp hybridized and then we still have our

two p orbitals

so in this kind of a picture we can have this

this

kind of bonding in here this is our sp

so the yellow ones are our sp

hybridized orbitals then our two left

over p orbitals

can actually form our pi bonds

so we end up getting electron density above

above

and below and also another set

perpendicular to it so this is also behind

behind

that over there with the blue atomic orbitals

orbitals

so this is what really is powerful about valence

valence

bond theory is that we can get an actual picture

picture

of what the bonding actually looks like

and we can describe the bonding as

a series of sigma bonds and pi bonds

what this will also allow us to do is to understand

understand

something else a little bit more

complicated and what we can also understand

understand

is this concept of delocalization

on here so this is actually the lewis

structure of the benzene model

model and it's very flawed because we

have to draw two different lewis structures

structures

to kind of explain what is actually

going on

in here because in reality what we have

is some sort of molecule

that we can express kind of like this

where we have electron density

that is in a circular kind of fashion

so all of these atomic orbital are these

uh carbon atoms

are all sp2 hybridized which means that

there is a p

orbital to form those pi interactions

and then all the carbon atoms will have

some sort of p

orbital that is available for bonding

and this creates the ring of electron density

density

the benzene ring

so to give you a better picture of this

what we can do is we can go to this

website kentube3d.com

and we can look at the benzene orbitals

on here

so here's a picture of the benzene

orbitals on here

so uh in the picture in the upper right

hand corner you can see the sp2

hybridized forms all the sigma bonds

on here so we can go ahead and first

think about all the sp2

hybridized orbitals and they form these

kind of orange kind of orbitals on here

so that works really great and then what

we have left over

are our remaining p orbitals that are

drawn above and below

and what we end up getting is a ring of

electron density

and this is what we call delocalized

electrons and that's really important

for this benzene molecule

so we end up getting these p orbitals

that can form this ring like of

electron density on here

and then if we actually show the

resulting bonding orbital

on here we see that we end up getting a

whole bunch of pi

interactions above and below

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