Nitration of Methyl Benzoate

Nitration of Methyl Benzoate

Purpose:

The purpose of this experiment is to synthesize methyl nitrobenzene from methyl benzoate, concentrated nitric acid, and concentrated sulfuric acid via an electrophilic aromatic substitution reaction.

Introduction

Nitration is an example of electrophilic aromatic substitution, and in this experiment the goal was to successful add a nitro group to methyl benzoate using nitric acid and sulfuric acid as a reagents, and vacuum filtration and centrifugation for isolation. Electrophilic aromatic substitutions are reactions in which a hydrogen atom on an aromatic ring is replaced by an electrophile. Methyl 3-nitrobenzoate will be synthesized by nitrating methyl benzoate.

Reaction Mechanism:

Physical Data

Vial + methyl benzoate = 18.385g Nitric Acid M.W. = 63.01g/mol

Crude Solid = 1.04 g Amount Used = 2mL

Methanol (from volume) = 0.78 mL Boiling Point =

Melting Point =

Recrystallized Solid = 1g Refractive Index =

Melting Point = 75°C Density =

Methyl Benzoate M.W. = 136.16g/mol Sulfuric Acid M.W. = 98.09g/mol

Amount Used = 3g Amount Used = 6 mL

Boiling Point = Boiling Point =

Melting Point = Melting Point =

Refractive Index = Refractive Index =

Density = Density =

Methyl m-Nitrobenzoate M.W. = 181.15g/mol Methanol M.W. = 32.04g/mol

Boiling Point = Amount Used =

Melting Point = Boiling Point =

Refractive Index = Melting Point =

Density = Refractive Index =

Density = 1.33141

Procedure

Nitration of Methyl Benzoate

Prepare an ice bath using a 150 mL beaker. Pour about 6 mL of concentrated sulfuric acid into a 50 mL beaker and place the beaker in the ice bath. Allow it to remain for 10 minutes where it should cool to ice temperature.

Obtain a vial containing a sample of methyl benzoate. Weigh the sample.