Nucleophilic Aromatic Substitution of 2,4-Dinitrochlorobenze
Experiment #1
Nucleophilic Aromatic Substitution of 2,4-dinitrochlorobenze
Name: Anouk Deck-Leger
Student I.D: 9380868
Date performed: September 13th, 2010
Due Date: September 20th, 2010
Introduction:
The company DNCB produces large amounts of 2,4-dinitrochlorobenzene and they sell this product to treat against warts and severe and chronic hair loss. It can also be used as an alternative treatment for HIV.
The supervisor notices an excess amount of m-aminobenzoic acid stored away which is currently not being used for anything. This reactant can be used in certain reactions to produce valuable solutions for ophthalmologists. This product is going to waste, and our objective is to see if we can obtain a usable end product when reacting m-aminobenzoic acid with 2,4-dinitrochlorobenzene. In order for this reaction to take place, we must verify that we can obtain a product through the following nucleophilic aromatic substitution reaction:
When electron withdrawing groups are present on a benzene ring, the ring can more easily undergo a nucleophilic attack. In this reaction we are dealing with a halogen (Cl) placed on the benzene ring, and when the electron withdrawing group is present either in ortho or para positions the nucleophilic attack will attack with more ease than if the EWG is positioned on meta carbon or when there are no EWG's present at all.
Both reactants, the m-aminobenzoic acid and the 1-chloro-2,4-dinitrobenzene, were mixed together and were dissolved using dimethylformamide. The resultant solution was heated, mixed with deionized H2O and vacuum filtrated in order to separate our formed product form the solvent. This technique was further repeated after our product was washed with heated ethanol. The final product was m-(2,4-dinitroanilino) benzoic acid. The reaction mechanism for the overall reaction in question is as follows:
Results & Observations:
Mass of 2,4-dinitrochlorobenzene = 1.012g
Mass of m-aminobenzoic acid =
Nucleophilic Aromatic Substitution of 2,4-dinitrochlorobenze
Name: Anouk Deck-Leger
Student I.D: 9380868
Date performed: September 13th, 2010
Due Date: September 20th, 2010
Introduction:
The company DNCB produces large amounts of 2,4-dinitrochlorobenzene and they sell this product to treat against warts and severe and chronic hair loss. It can also be used as an alternative treatment for HIV.
The supervisor notices an excess amount of m-aminobenzoic acid stored away which is currently not being used for anything. This reactant can be used in certain reactions to produce valuable solutions for ophthalmologists. This product is going to waste, and our objective is to see if we can obtain a usable end product when reacting m-aminobenzoic acid with 2,4-dinitrochlorobenzene. In order for this reaction to take place, we must verify that we can obtain a product through the following nucleophilic aromatic substitution reaction:
When electron withdrawing groups are present on a benzene ring, the ring can more easily undergo a nucleophilic attack. In this reaction we are dealing with a halogen (Cl) placed on the benzene ring, and when the electron withdrawing group is present either in ortho or para positions the nucleophilic attack will attack with more ease than if the EWG is positioned on meta carbon or when there are no EWG's present at all.
Both reactants, the m-aminobenzoic acid and the 1-chloro-2,4-dinitrobenzene, were mixed together and were dissolved using dimethylformamide. The resultant solution was heated, mixed with deionized H2O and vacuum filtrated in order to separate our formed product form the solvent. This technique was further repeated after our product was washed with heated ethanol. The final product was m-(2,4-dinitroanilino) benzoic acid. The reaction mechanism for the overall reaction in question is as follows:
Results & Observations:
Mass of 2,4-dinitrochlorobenzene = 1.012g
Mass of m-aminobenzoic acid =
References: 1)Introduction to Spectroscopy, 3rd Edition, Pavia, Lampman Kriz and Vyvyan,Brooks/Cole, 2009. 2)Robidoux, Muchall, Rogers. “Experiment 1: Nucleophilic aromatic substitution of 2,4-dinitrochlorobenzene” Organic Chemistry III Laboratory manual. Concordia university, July 2009, pages L-15 to L-19. 3)Nucleophilic Substitution, Elimination & Addition Reactions of Benzene Derivatives http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/benzrx2.htm, accessed Sept 20th, 2010 -------------------------------------------- [ 1 ]. Organic Chemistry III CHEM 324 Laboratory Manual, Robidoux, Muchall & Rogers. [ 2 ]. Wiki media http://en.wikipedia.org/wiki/Nucleophilic_aromatic_substitution