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Mechanism of Methyl Benzoate Nitration

The document describes the nitration of methyl benzoate using nitric acid and sulfuric acid. The main product is the meta-nitrated derivative (50% yield). Side products include the ortho- and para-nitrated isomers (each with a yield of 25%). The procedure involves dissolving methyl benzoate in sulfuric acid and slowly adding a mixture of nitric and sulfuric acids while cooling to 0°C. The reaction mixture is then allowed to warm to room temperature before being poured onto ice. The product is filtered, washed, recrystallized from methanol, dried, weighed, and had its melting point determined.

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279 views29 pages

Mechanism of Methyl Benzoate Nitration

The document describes the nitration of methyl benzoate using nitric acid and sulfuric acid. The main product is the meta-nitrated derivative (50% yield). Side products include the ortho- and para-nitrated isomers (each with a yield of 25%). The procedure involves dissolving methyl benzoate in sulfuric acid and slowly adding a mixture of nitric and sulfuric acids while cooling to 0°C. The reaction mixture is then allowed to warm to room temperature before being poured onto ice. The product is filtered, washed, recrystallized from methanol, dried, weighed, and had its melting point determined.

Uploaded by

syedmuhammadtarique
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPT, PDF, TXT or read online on Scribd

Nitration of Methyl Benzoate

COOH COOCH3
CH3OH

H2SO4

COOCH3 COOCH3
HNO3, H2SO4

NO2
Multistep Synthesis

50% 50%
A B C

Yield = 25%
Ortho Meta Para

X Ortho

Meta
Para
Number Ring

6 X 2

5 3

4
Nucleophilic Aliphatic Substitution
HCl
(CH3)3COH (CH3)3CCl

Electrophilic Aromatic Substitution


H NO2
+
NO2 +
ARENE SUBSTITUTION

E
E+
+ H+

The electrophile REPLACES H +


Mechanism

H E-Y
Mechanism
H E-Y

H E H E H E
+ +

+
E

+ H+
Charge o and p
Energy Diagram
Nitration of Benzene
NO2
HNO3
H2SO4

Nitrobenzene
Nitration Reagent

HONO2 + 2 H2SO4 NO2+ + H3O+ + 2 HSO4-

Nitronium Ion
Nitration Mechanism
H H NO2
NO2+
+

NO2

+ H+
Multiple Substituents
G

G G

Second Group. Where go? How fast?


Nitration of Toluene
CH3
HNO3

CH3 CH3 CH3

NO2

NO2
NO2
63% 3% 34%
ORTHO Compare
CH
o, m, p CH3
3
NO2 NO2
+ H H
+ +
META CH3 CH3 CH3

+ +
NO2 NO2 NO2
H H
+ H

PARA CH3 CH3

+
+ +
H H NO2
NO2
Electron Donating Groups
Favor: ORTHO and PARA.

Electron
Donating G
Ortho

Para
Nitration of
trifluoromethylbenzene
CF3
HNO3

H2SO4

CF3 CF3
CF3

NO2
NO2
NO2

6% 91% 3%
Electron Withdrawing Groups

CF3 + charge
here bad
Ortho Compare o, m, p CF3
CF3 CF3
H H H
+
NO2 NO2
+ NO2 +

Meta
CF3 CF3
+ +
H H

+ NO2 NO2

Para
+
+ +
Electron Withdrawing Groups
Meta Directors and DEACTIVATING
Electron
Withdrawing Z
Group

Meta Product
Ortho-Para Directors
-NH2 Very Activating
-NHR
-OH
-OR
O
-NHCR
O
-OCR
Ortho-Para Directors

-R Activating

-Ar Activating

-Halogens Deactivating
Meta Directors
O
-SO3H
-CR
O -NO2
-COH
-CN
Main Reaction
COOCH3 COOCH3
HNO3, H2SO4
meta
NO2

Side Products
COOCH3 COOCH3
COOCH3
NO2

O2N NO2
NO2
Procedure
1. Dissolve methyl
benzoate in H2SO4

2. Mix HNO3 and


H2SO4 at 0oC

3. Add HNO3 / H2SO4


dropwise to methyl
benzoate at 0oC
Procedure
4. Let stand at room
temperature 10
minutes

5. Pour onto ice


Filter
Wash

Recrystallize from
methanol

Dry

Weigh

m.p.

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