nitration of methyl benzoate
DESCRIPTION
Nitration of Methyl Benzoate. Multistep Synthesis. 50%. 50%. C. B. A. Yield =. 25%. Ortho Meta Para. Ortho. Meta. Para. Number Ring. 6. 2. 3. 5. 4. Nucleophilic Aliphatic Substitution. Electrophilic Aromatic Substitution. ARENE SUBSTITUTION. E +. + H +. - PowerPoint PPT PresentationTRANSCRIPT
(CH3)3COH (CH3)3CClHCl
Nucleophilic Aliphatic Substitution
NO2
++
H NO2
Electrophilic Aromatic Substitution
CH3NO2
H
CH3NO2
H+
+ +
CH3
NO2
H
CH3
NO2
H
CH3
NO2
H
CH3
NO2H
CH3
NO2H
+
+
+
+ ++
ORTHO
META
PARA
Compare o, m, p
Z
Meta Directors and DEACTIVATING
ElectronWithdrawing Group
Meta Product
Electron Withdrawing Groups
1. Dissolve methyl benzoate in H2SO4
2. Mix HNO3 and H2SO4 at 0oC
3. Add HNO3 / H2SO4
dropwise to methyl benzoate at 0oC
Procedure