BenZene Ractions Dr Md Ashraful Alam Assistant Professor Department of Pharmaceutical Sciences.
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Transcript of BenZene Ractions Dr Md Ashraful Alam Assistant Professor Department of Pharmaceutical Sciences.
![Page 1: BenZene Ractions Dr Md Ashraful Alam Assistant Professor Department of Pharmaceutical Sciences.](https://reader036.fdocuments.in/reader036/viewer/2022062804/5697bf7d1a28abf838c84e1f/html5/thumbnails/1.jpg)
BenZene Ractions
Dr Md Ashraful Alam
Assistant Professor
Department of Pharmaceutical Sciences
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• Benzene does not undergo electrophilic addition
• It undergoes electrophilic aromatic substitution maintaining the aromatic core
• Electrophilic aromatic substitution replaces a proton on benzene with a.nother electrophile
2
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3
electrophilic aromatic substitution
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Electrophilic Aromatic Substitution
HE
E
HE
+ H-base:base
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Ortho-Para and Meta Directing Substituents
• When substituted benzenes undergo further substituents, the substituent group present in the benzene derivative will influence electrophilic substitution in 2 ways which are:
i) Reactivity
ii)Orientation
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EFFECTS OF SUBSTITUENTS ON THE REACTIVITY OF ELECTROPHILIC
AROMATIC SUBSTITUTION• Substituent group present in the benzene ring can
influence the rate of reaction of further substitutions.
• Electron-donating groups make the ring more reactive (called activating groups) thus influence the reaction become faster.
• Electron-withdrawing groups make the ring less reactive (called deactivating groups) thus influence the reaction become slower.
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• A substituents group already in the ring influences the position of further electrophilic substitution whether at ortho, meta or para position.
• Ortho-para directors: the groups that tend to direct electrophilic substitution to the C2 and C4 positions.
• Meta directors: the groups that tend to direct electrophilic substitution to the C3 position.
EFFECTS OF SUBSTITUENTS ON THE ORIENTATION OF ELECTROPHILIC
AROMATIC SUBSTITUTION
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Effetcs of substituent groups on the benzene ring
Activating groups (electron donating)
Deactivating groups
(electron-withdrawing)
-NH2 -R
-OH
-OR
-NHCOCH3
-F
-Cl
-Br
-I
ortho-para directors ortho-para directors
meta directors
C
O
R
C
O
OH
C
O
OR
SO3H
C N
NO2
NR3
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Disubstituted Benzenes : Orientation
Orientation Effects of Substituents in Electrophilic Aromatic Substitution :
Ortho , para directors Meta directors
-OH, -OR-NH2, -NHR, -NR2-C6H5-CH3, -R (alkyl)-F, -Cl, -Br, -I
-NO2-SO3H-COOH, -COOR-CHO, -COR-CN
OH OH
NO2
NO2
nitration
NO2
NO2
nitration+
OH
NO2o-Nitrophenol p-Nitrophenol
53 47
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10
Substituent Effects in Aromatic Rings • Substituents can cause a compound to be (much)
more or (much) less reactive than benzene• Substituents affect the orientation of the reaction
– the positional relationship is controlled– ortho- and para-directing activators, ortho- and para-
directing deactivators, and meta-directing deactivators
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11
Activators/Deactivators
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Specific Electrophilic Aromatic : Substitution Reactions
X2 , FeX3
Halogenation
X
+ HX (X=Cl, Br)
RCl, AlCl 3
Alkylation
R
+ ClH
HONO2 , H2SO4
Nitration
NO2
+ OH2
SO3 , H2SO4
Sulfonation
SO3H
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EAS Reactions of Benzene
Br
NO2
SO3H
CR
O
Cl
IR
CHO
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• Benzene’s electrons participate as a Lewis base in reactions with Lewis acids
– Lewis acid: electron pair acceptor
– Lewis base: electron pair donor
• The product is formed by loss of a proton, which is replaced by a halogen
14
Bromination / Chlorination
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H BrBr2, FeBr3
+ HBr
H ClCl2, FeCl3
+ HCl
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Bromination Mechanism
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Nitration
HNO3, H2SO4NO2
+ H2O
HNO3 + H2SO4 NO2+ + H2O + HSO4
-
Formation of electrophile
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Nitration Mechanism
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Nitration of Toluene
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Sulfonation is Reversible
HSO3, H2SO4
SO3Hfuming sulfuric acid
S
O
OO H OSO3H
SO3H
HOSO3H
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Desulfonation
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Friedel-Crafts Acylation
RCCl, AlCl3
O C
O
R+ HCl
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1st, Formaton of Electrophile
C
O
R Cl AlCl3
+ -
RC
O
R C O AlCl4
acylium ion
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Acylation Mechanism
C
O
R
C
O
RH Cl AlCl3
CR
O
+ HCl
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Intermediate is Resonance-Stabilized
C
O
RH
C
O
RH
C
O
RH
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An Acylation
CH3
CH3
CH3CH2CH2CH2CCl
O
TiCl4 in CH2Cl2
CCH2CH2CH2CH3
OCH3
CH3
+ HCl
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Friedel-Crafts Alkylationmany more limitations
RX, AlCl3R
+ HCl
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Mechanism
CH3 C
CH3
CH3
Cl AlCl3 C
CH3
CH3
CH3
t-butyl carbocation
AlCl4
CH3 C
CH3
CH3
(CH3)3C
H
(CH3)3C (CH3)3C
resonance stabilized intermediate
Cl AlCl3 (CH3)3C
+ HCl(+ AlCl3)
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Carbocation Generated From Alkene
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Unexpected Product?
CH3CH2CH2CH2Cl, AlCl 3
CH2CH2CH2CH3
CHCH2CH3
CH3
minor product
major product
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Carbocations Rearrange…
CH3CH2CH2CH2 Cl AlCl3 CH3CH2CHCH2
H
CH3CH2CHCH3
hydride shift
2o
1o
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1o RX Typically Undergoes Shift
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Side Chain Reactions
O
H2, Pd/C
in ethanol
1) Reduction of Aromatic Ketones
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Straight-chain Alkylation can be Accomplished in 2 steps:
Acylation, then Reduction
CH2CH2CH3
CCH2CH3
O
CH3CH2CH2Cl
AlCl3 minor
CH(CH3)2
+
CH3CH2CCl
AlCl3
O
major
H2, Pd/C
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2) Oxidation of Alkyl SubstituentsCH3
KMnO4, H2O
COH
O
KMnO4
H2O
CO2H
CH3
CH(CH3)2
KMnO4, H2OCO2H
CO2H
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3) Benzylic Bromination with NBS
H
NBS, CCl4, h
Br
NBr
O
O
NBS
benzylic hydrogen
N-Bromosuccinimide
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4) Alkali Fusion of Sulfonic Acids
phenol
SO3H1) NaOH, 300 C
2) H3O+
OHo
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5) Reduction of Nitro Groups
NO21) SnCl2, HCl2) NaOH
or H2 on Pt
NH2
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Directing Effects
EDG EWG
electron donating groups electron withdrawing groups activate ring deactivate ring
atom attached isusually sp3
atom attached isusually sp or sp2
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ortho/para-Directing Activating Groups
OCH3 OCH3 OCH3 OCH3
OCH3
+
- -
-
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Nitration of Anisole
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Nitration Affords ortho and para Products
OCH3
HNO3, H2SO4
OCH3
NO2
OCH3
NO2
+
ortho para
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Activating ortho/para directors
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meta-Directing Deactivating Groups
CH
O
CH
O
CH
O
CH
O
CH
O
+
+ +
-
ortho and para positions
are deactivated toward
EAS
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Electron-Withdrawing Nitro Group Directs meta
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meta Directors
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Comparison
CH3
CF3
Br2, FeBr3
ortho meta para
Brominated product
63 3 34
6 91 3
ortho meta para
rel. rate
25
0.000025
rate rel. to benzene
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More Limitations with Friedel Crafts Reactions
Cl
Ring must be at least as activated (reactive) as
NO2 ClCCH3, AlCl3
O
No Reaction
Cl
CH2CH3
+ orthoCH3CH2Cl, TiCl4
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Substituent Summary
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Halogens are the AnomolyDeactivators and o,p-Directors
Br
CH3CH2Cl
AlCl3
Br
CH2CH3
CH2CH3
Br
+
rel. rate = 0.5
Inductively withdrawing, hence deactivatingResonance donation causes o,p directing
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Reactions of Rings With Two or More Substituents
NO2
OCH3 OCH3
NO2
ClCl2, FeCl3
Activating Group Controls Reaction
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The (More) Activated Ring Reacts
CO
OH2SO4
SO3
CO
O
SO3H
deactivated activated(+ some ortho)
*
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Mixtures with Conflicting Directing Effects
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Provide the Reagents
NH2
C(CH3)3
Br
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Must Acylate FirstNH2
ClCCH2CH2CH2CH3
O
AlCl3
O meta director
HNO3
H2SO4
O
NO2
H2, Pt/C
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Sulfonic Acid Blocks para Position C(CH3)3
Br
H(CH3)3CBr
AlCl3
C(CH3)3
SO3, H2SO4
SO3H
C(CH3)3
Br2, FeBr3
C(CH3)3
SO3H
Br
H3O+
blocks para
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Give the Reagents
CO2H
O
CH3Cl
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Provide the Reagents
CH2CH3
OHBr
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CH2CH3
OHBr
1) ClCCH3, AlCl3
O
2) SO3, H2SO4
3) Br2, FeBr3
4) H2 Pd/C5) NaOH, 300 C
o
6) H3O+
O O
SO3H
O
SO3HBr SO3HBr
1)
2) 3) 4)
5,6)
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Provide the Reagents
HO2C
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HO2C1)
Cl
AlCl3
2) Cl
O AlCl33) KMnO4, H2O
4) H2, Pd/C
5) NBS, h6) NaOCH3 in CH3OH, heat
(E2 elim of HBr)
1)
O
2)
O
HO2C3)
HO2C
HO2C
Br
4)
5)
6) workup w/ H3O+
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65
Reactions of Benzene