Effect of Substituent groups
on Benzene
Prof Dr Akkaladevi Muralidhar Rao
M.Pharm,PhD
St.Mary’s College Of Pharmacy
Secunderabad
H 2 SO 4
H 2 SO 4
CH 3
H 2 SO 4
NO 2
?
?
Can you guess ?
Which reaction is fast and why?
Possible products ?
Benzene
Nitro benzene
A
B
C
• Reaction A : Benzene reacts completely within
20 to 30 minutes and single product
• Reaction B: Toluene reacts within 1 minute
• Reaction C: Nitrobenzene reacts within 2
hours.
• elecrophilic substitution reactions -Typical
reactions of benzene
• What about alkenes?
• Ortho and para director
• Meta director
Effect of Group
• Any Group attached to a benzene ring affects
the reactivity of the ring
• Determines the orientation of the substitution
• Attack by electrophilic reagent -
how readily the attack occurs?
where it occurs ?
Activating group
(O and P directors)
Deactivating groups
(M directors)
CH3
OCH3
OH
NH2
Reaction is fast
Release electrons to the ring by
resonance and make it electron
rich
NO2
COOH
CN
Reaction is slow
Removes electrons from the ring
by resonance and make it
electron deficient
EXCEPTIONS
HALOGENS ARE DEACTIVATING GROUPS BUT
O & P DIRECTORS
F Cl Br I

effect of substituent groups

  • 1.
    Effect of Substituentgroups on Benzene Prof Dr Akkaladevi Muralidhar Rao M.Pharm,PhD St.Mary’s College Of Pharmacy Secunderabad
  • 2.
    H 2 SO4 H 2 SO 4 CH 3 H 2 SO 4 NO 2 ? ? Can you guess ? Which reaction is fast and why? Possible products ? Benzene Nitro benzene A B C
  • 3.
    • Reaction A: Benzene reacts completely within 20 to 30 minutes and single product • Reaction B: Toluene reacts within 1 minute • Reaction C: Nitrobenzene reacts within 2 hours.
  • 4.
    • elecrophilic substitutionreactions -Typical reactions of benzene • What about alkenes?
  • 6.
    • Ortho andpara director • Meta director
  • 7.
    Effect of Group •Any Group attached to a benzene ring affects the reactivity of the ring • Determines the orientation of the substitution • Attack by electrophilic reagent - how readily the attack occurs? where it occurs ?
  • 8.
    Activating group (O andP directors) Deactivating groups (M directors) CH3 OCH3 OH NH2 Reaction is fast Release electrons to the ring by resonance and make it electron rich NO2 COOH CN Reaction is slow Removes electrons from the ring by resonance and make it electron deficient
  • 9.
    EXCEPTIONS HALOGENS ARE DEACTIVATINGGROUPS BUT O & P DIRECTORS F Cl Br I