(2,4,82,38) Reaction Mechanism of Nitration11

REACTION MECHANISM OF NITRATION
GROUP MEMBERS
 2017-CH-02
 2017-CH-04
 2017-CH-38
 2017-CH-82
 NITRATION:
Nitration is a general class of chemical process for the introduction of a nitro group into an organic
chemical compound. More loosely the term also is applied incorrectly to the different process of forming
nitrate esters between alcohols and nitric acid, as occurs in the synthesis of nitroglycerin.
 GENERAL MECHANISM OF NITRATION

In general, nitration is the process of adding a nitro group to an organic substrate. The most common
form of nitration is adding the nitro group to an aromatic ring system. The nitration reaction
mechanism involves: Formation of the nitronium ion by the action of nitric and sulfuric acids
 NITRATION MECHANISM OF ALKANES:

Another reaction of commercial importance is the nitration of alkanes to give nitroparaffins. Such
reactions usually are carried out in the vapor phase at elevated temperatures using nitric acid
(HNO3HNO3) or nitrogen tetroxide (N2O4N2O4) as the nitrating agent:
All available evidence points to a radical mechanism for nitration, but many aspects of the reaction are
not fully understood. Mixtures are obtained; nitration of propane gives not only 1- and 2-nitropropanes
but nitroethane and nitromethane:
In commercial practice, the yield and product distribution in nitration of alkanes is controlled as far as
possible by the judicious addition of catalysts (e.g., oxygen and halogens), which are believed to raise
the concentration of alkyl radicals. The products are separated from the mixtures by fractional
distillation
https://chem.libretexts.org/Textbook_Maps/Organic_Chemistry/Book
%3A_Basic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)/04._Alkanes
/4.6%3A_Nitration_of_Alkanes
 NITRATION MECHANISM OF ALKENES AND ALKYNES:
https://www.google.com/url?
sa=i&source=images&cd=&cad=rja&uact=8&ved=2ahUKEwinwLTz1JTfAhVXU30KHb
XrD_EQjRx6BAgBEAU&url=https%3A%2F%2Ffanyv88.com%3A443%2Fhttp%2Fchemistryallclass.blogspot.com
%2F2015%2F08%2Fpreparation-of-
alkane.html&psig=AOvVaw0NFd0gWSesLbyZdwMEGXY_&ust=1544510555333362
 NITRATION OF TOULENE:
https://www.google.com/url?
sa=i&source=images&cd=&cad=rja&uact=8&ved=2ahUKEwj4-
NrU1JTfAhXLbisKHSS1BSgQjRx6BAgBEAU&url=https%3A%2F
%2Fwww.masterorganicchemistry.com%2F2017%2F11%2F09%2Felectrophilic-
aromatic-substitution-the-mechanism
%2F&psig=AOvVaw0NFd0gWSesLbyZdwMEGXY_&ust=1544510555333362
 NITRATION MECHANISM OF BENZENE:

The electrophilic substitution reaction between benzene and nitric acid
The facts
Benzene is treated with a mixture of concentrated nitric acid and concentrated sulphuric acid at a
temperature not exceeding 50°C. As temperature increases there is a greater chance of getting more
than one nitro group, -NO2, substituted onto the ring.
Nitrobenzene is formed.
or:
The concentrated sulphuric acid is acting as a catalyst.
The formation of the electrophile

The electrophile is the "nitronium ion" or the "nitryl cation", NO2+. This is formed by reaction between
the nitric acid and the sulphuric acid.
 The electrophilic substitution mechanism
Stage one
Stage two
https://www.chemguide.co.uk/mechanisms/elsub
/nitration.html
 NITRATION MECHANISM OF PHENOL:
Phenols upon treatment with dilute nitric acid undergo nitration at low temperature (298 K) to give a
mixture of ortho and para nitrophenols. The mixture formed is further separated into ortho and para
nitrophenols by steam distillation on the basis of their volatility. Due to intramolecular and
intermolecular hydrogen bonding, ortho nitrophenols are lesser volatile in comparison to para
nitrophenols which involves only intermolecular hydrogen bonding.
When phenol is treated with concentrated nitric acid, the nitration results in the formation of 2, 4, 6-
trinitrophenol (commonly called picric acid).
https://byjus.com/chemistry/phenol-electrophilic-substitution/
 NITRATION MECHANISM OF ACETANIEE:
LIDE: Here is the mechanism for the nitration of acetanilide to form p-nitro
acetanilide
http://uipspuchd.blogspot.com/2013/03/nitration-of-acetanilide-p.html
o IMPORTANCE OF NITRATION:
 IN INDUSTRY
Aromatic nitration has long been an important process in industrial chemistry for nitro-aromatic
products are widely used as explosives, solvents, pharmaceuticals and intermediates in the
manufacture of synthetic dyestuffs and other chemicals. The nitrating agent most commonly used
industrially for aromatic mononitrations is an aqueous mixture of nitric and sulphuric acids, typically
15 mole % HNO3, 30 mole % H2SO4 and 55 mole % H2O. The organic substrate, together with the
nitro product, forms a separate phase from the aqueous mixed acid and so mass transfer is involved
simultaneously with chemical reaction. The reaction mixture should be well stirred, therefore, to
minimize the mass transfer resistances, although these may never be completely overcome. The
mixed acid generally gives the wanted nitro product more quickly, at a lower temperature and with
less loss through higher oxidation reactions than when nitric acid alone is used.
https://pubs.acs.org/doi/abs/10.1021/bk-1976-0022.ch008
 IN FERTILIZERS
The most common form of nitration is that of C-nitration, particularly of aromatic compounds. It is also
possible to carry out derivatizations of oxygen and nitrogen functionalities using nitration chemistry. For
e.g. the formation of nitrate esters is well documented and nitroglycerine (used as vasodilator in the
treatment of acute angine, as well as being one of the most famous explosives in the world) is
manufactured by the nitration of glycerin using a traditional mixed acid reaction N-nitration is usually
followed by rearrangement of the nitramine intermediate formed by reaction of amine substrate with
nitronium ion.
http://www.iptonline.com/articles/public/IPTSEVEN132NP.pdf

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REACTION MECHANISM OF NITRATION

 GENERAL MECHANISM OF NITRATION

 NITRATION MECHANISM OF ALKANES:

 NITRATION MECHANISM OF ALKENES AND ALKYNES:

 NITRATION MECHANISM OF BENZENE:

The concentrated sulphuric acid is acting as a catalyst.

The formation of the electrophile

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