Reaction Mechanism: Definition

REACTION MECHANISM
Definition:
Actual changes undergone by reacting molecules to reach the product state or
sometimes people talk about chemical steps necessary for one molecule to be
transformed to another.
So essentially if you're thinking of going from say destination A to destination B, you
can even think of traveling by road to one destination to another, reaction mechanism
essentially is something similar where your two destinations are your reactant and your
product and the road essentially is your reaction mechanism.
Now, what you would see is one can propose what you would call a most probable
mechanism but it is not definitely possible to say with 100% confidence that this is the
only mechanism for the reaction.
Again, just like I told you for the earlier example of going from destination A to B, you
can take one road to reach from A to B, but that might not be the only road. You might
have different roads which take you from A to B. So you can say with 100% confidence
that this might be the fastest road to reach from A to B but what you cannot say with
100% confidence is this is the only road to reach from A to B.
Classification of Organic Reactions: (Polar, Radical and Concerted)
1. Polar mechanism:
In a polar mechanism just like the name suggests, you have two intermediates which are
charged so one would be positively charged and the other would be negatively charged
and they would come together to give your product.
For intermediates terms like nucleophile, electrophile, Lewis base, Lewis acid, donor,
acceptor is used.
Essentially, what all that means is you have some electron rich species and some
electron deficient species. So since we are talking about organic reactions which
essentially involve carbon, if I were to look at carbon and another species now if X right,
now if X is carbon so if you are thinking of C-C what you see is both of these atoms
would take the electrons of the bond in a similar fashion to each other.
So now if you have two atoms- C, X where X has a greater tendency to pull electrons to
itself, now what will happen is X will end up having a large electron density over itself
and carbon will have less electron density with itself.
So even with a neutral molecule what you end up generating is a small positive charge
and a small negative charge. Alright? Which is very essential for polar reactions.
So there are three effects i.e. inductive effect, resonance effect and hyperconjugation.
(1). Inductive effect:
Inductive effect it is essentially the phenomenon of withdrawing electrons through
sigma bonds and here comes a very important concept of electronegativity. So If X is an
electronegative atom, what electronegative means is that X has a greater tendency to
pull electrons towards itself from this bond. Now as it pulls electrons what you end up
getting is you end up getting a δ- or a small negative charge and a δ+ which is a small
positive charge on the carbon.
Imagine if you have two friends standing next to each other and you have a bag of
chocolates the stronger one would end up pulling it pulling more of the chocolates
towards themselves. So similarly here, instead of chocolates we are talking about
electrons. So if X is more electronegative it will tend to grab more electrons towards
itself and as you know electrons are negatively charged hence you get a δ-, now so that
you can compare like two friends I said one is stronger to compare which is more
electronegative there is a scale called as Pauling scale and what Pauling scale does is it
ranks atoms based on their electronegativity.
Now I have shown you a table here and this concept is called as group electronegativity.
(2). Resonance effect:

So now that we have some idea of the inductive effect, another effect, now in this effect,
the lone pairs play a very important role. This effect is called as resonance effect. So
resonance effect is where you have multiple Lewis structures for the same compound.
Movement of electrons:
So one way or the convention to show movement of electrons is what is called as arrow
or electron pushing. This depicts movements of electrons or electron pairs. This is very
useful in writing multiple Lewis structures in a very systematic way. So the arrow
pushing or electron pushing depicts movement of electrons in a way such that you go
from an electron rich species which is your source, and to the sink which is electron
poor.
Rules for resonance:

1. Only electrons move around. All nuclei in the same position.
Remember the net charge of the structures remains the same.
2. Some structures are more favorable and contribute more.
The structure would be more favorable because you have a negative charge on an
electronegative atom, whereas here you have a positive charge on an electronegative
atom. So it will be a very minor contributor.
3. All atoms should be in one plane.
4. Remember the octet rule while writing the structures.
Exercise:
Draw plausible resonance structure for the following molecule? Which resonance
structure will contribute more?
Solution:
If I were to push electrons I had also taught you how to push electrons. So now there
are
these lone pairs on the nitrogen, so if I were to push electrons, I can push it this way and
now
because here I have too many electrons, I would push it again to the oxygen. So one
resonance
structure would be, so I have put a new pi bond here.
2. Radical mechanism:
In the radical mechanism you do not have charged intermediates, what you have is
radicals which would come together to give you your product.
3. Concerted reactions:
In these reactions all the bonding changes occur at the same time. So essentially there
are no intermediates involved in these reactions.

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REACTION MECHANISM

(2). Resonance effect:

Rules for resonance:

4. Remember the octet rule while writing the structures.

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