Diazonium Salt Reactions (Part - 26) - Organic Compounds containing Nitrogen, Chemistry Video Lecture - Class 12

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fear from exam let's talk about some of
the chemical reactions that are shown by
this diazonium shorts the first is the
reaction involving displacement of
nitrogen so if I have my salt here they
are reaction where my n2 is displaced so
examples for such kind of reactions are
replacement by a light or cyanide ions
replacement off into my iodine the
placement of in two by a fluoride ion
the placement of into by hydrogen
replacement by hydroxyl groups
replacement by no.2 you'll also have
some reactions where the dice group
that's into loop is retained and that is
called coupling in the action so we will
understand this kind of reaction one set
of reaction where and togepi's displays
one set of reaction where and to room is
retained at lian to is a nitrogen it
escapes out easily so you'll see motion
reactions into group is this place
alright so if we see this placement of
n2 if you see diazonium which i have
here in 2 plus that suppose CL - this is
a very good living room very good you
know it can easily be substituted by my
CL minus BR minus ID CN - Washburn's
because n2 escapes from the mixture as a
gas this n2 will escape from the mixture
as gas so let's talk about this
replacement by halide or cyanide so
halide is my CL minus BR - I -
insanity is my scene winds correct so
typical reaction is a I am my er in two
plus X minus this is my typical general
formula my diazonium salt aromatic
barium salt so if i react this guy with
cucl and some HCL but I get as a RCL
then into gas so the CL minus is
replacing this whole into X into goes
off and X minus s it was pleased with CL
but react this with CBR and HBR I will
get aromatic this one this is Bravo
benzene MIT in gas goes off similarly if
I want a cyanide one I'll react this
with see you see in and KC in but I will
get is and to go so when X minus s is
pleased with CML you get ya CN to gasp
oh so correct so here if you see what
I'm using is Cu with one charge is one
here Cu one fight and halogen acid and
this reaction is called San Mae reaction
this reaction is got sangmi a reaction
other option is what you can do is you
can use see you in HCl this will also
give you AR CL into gas and Cu excess or
just copper with let suppose HBR you
will get AR BR with nitrogen gas and Cu
X so here we are using halogen assets in
the presence of copper powder here I was
using copper with one oxidation number
here I'm using just copper powder this
reaction is called Gutterman reaction to
reaction sanwei reaction is better than
gamma
Gutterman reaction but there are two
different reactions to form to displace
nitrogen by halide or cyanide
let's see replacement by iodine tell me
one thing if I am benzene ring if I want
to introduce some iodine here something
like this how easy it is it is not that
easy
correct I can't introduce iodine just
like that in the benzene directly so
here what we do will use dyes named salt
for example if I have n 2 CL this
benzene dyes nutrilite know if I react
with the key I what I will get is this
plus obviously I'll get some KCl and
nitrogen gas the point I'm trying to
prove here is with diazonium salt it's
very easy to introduce iodine to Betty
similarly you'll see that other
compounds also it's very easy to
introduce attention benzene because of
diazonium salt here but we saw that
iodine we could easily introduce
same thing if I want to introduce in
this benzene fluorine it's really
difficult do it directly so here also
what we can do is we can take this
diazonium salt and react with HB f 4
that is fluoro boric acid what will
happen is this will form a + 2 + BF 4 -
again this is also a my died is named
sword from this I can get ya ba 3 also
comes out and nitrogen goes off the only
thing you will do is you to eat this so
I can easily get a fluorine now waiting
so these dyes ellipsoids helps to get
flowing in iodine this kind of atoms on
busy the next is the replacement by H so
if you see if you use mind reducing
agent like hypo phosphorous acid
or if none this will reduce diazonium
salts to greens and they'll oxidized to
phosphoric acid and Ethan a large key
for example I'll show you this is my tie
is indium salt if I use hypo phosphorus
as in this at 3 p o2 with some water
what would happen I will get normal
benzene right with the HP input just to
avoid any confusion because this is
replace by etch nitrogen comes up in s3
3 or 4 they themselves oxidized to
phosphoric acid to this s 3 p o3 and
some ratios
similarly you can use ethanol do the
same example I'm doing using ethanol to
oxidize this so to reduce this so what
will happen is this will become my non
benzene nitrogen comes up and this
ethanol will become neat that you know
obviously yes he'll also will come up
right so this is my displacement of
nitrogen my hydrogen we see there was a
nitrogen into CL it godness plays with
hydrogen you to use just mind reducing
agent this is very unstable - producing
it any will do here
the next is displacement of nitrogen by
hydroxyl group so if you increase the
temperature of this diazonium salt you
have this dies new salt
increase this temperature and you have
to react with water as me just mixing
water increase the temperature to maybe
283 Kelvin not at high almost room
temperature just increase to around
embrasure what happen is this salt get
hydrolyzed to phenol into gas comes up
and H and C will react to form s here
this is what you get pen on pretty easy
reaction since this part is unstable you
just have to warm this with water you
get C we see the whole end to see a
little place with watch the next we'll
see is will replace this into CL or n2x
with an o2 right Drago correct so in
this we use diazonium fluoro buried only
so this when you heat with across any
no.2 in presence of copper you heat this
you get something like this
my it remains the elation example so
let's start with then 2 CL first alright
first I'll make dye is a new hydro die
isn't even flora bore it because that is
what is required so I'll react this with
HB a for we have seen reaction this is
flora boric acid so what you will get
here is into bf4 - once I have diazonium
floor abhorrent I can react with any
no.2 copper and some amount of heat but
you get as
- nitrogen beans goes off and you get na
bf4 correct
so the typical reaction mechanism but
you want to displace this with night
no.2 please note you have to use Toro
Borat only so first year to convert to
go for it
as I told there is a reaction where we
retain daizo mu and this reaction is got
coupling the action I'll show you why
it's called coupling reaction so here my
Trojan is retained in the final product
right so here what happened is this
diazonium salt we have died this william
salt we get that reacts with other
electron rich electron rich aromatic
compound and the yield of product they
have the form law of this battle and
they are colored they also use for
dyeing because they are colored so my
dyes news all react with electron rich
aromatic compound it forms compound with
gel formula of yeah in double bond in ER
- this is a compound if you see nitrogen
is retained here right into is retained
and they are colored they are also used
for dye for example this is my benzene
dye as William chloride correct
react with phenol so this h and the CL
will react and form a CL and the final
product which you get out of this is
this and it is orange color life
it's called para hydroxy as o benzene
let's take some more example again I
will take benzene die as soon am
chloride you react with this time
manually you know so you take this
hydrogen here this hydrogen and this
chlorine will react this product this is
yellow color dye correct this is called
para amino benzene so my a phenomenal
gives orange color dye and Miami
annealing gives yellow color dye with
benzene diazonium salt let's talk about
the importance of this biennium salt as
a as we have seen also they are used as
good intermediates or introduction of
fluorine chlorine bromine iodine cyanide
oho inaudible with aromatic ring
sometimes it is difficult to introduce
these atoms directly to aromatic ring so
these diazonium salt are very good
intermediates for introduction of
fluorine chlorine bromine cyanide Oh a
ch2 groups in this correct because
sometimes to introduce this groups is
really difficult but these diazonium
salts helps us to achieve that
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