Nucleophilic Aromatic Substitution of 2,4-Dinitrochlorobenze Essay

1766 Words Oct 6th, 2010 8 Pages
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
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
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FT-IR spectrum
The major peaks are C=O, O-H, N-H, C=C, and NO2.1
A peak between 1660 and 1820 cm-1 (presence of C-O) and a broad peak between 2400 and 3400cm-1 (presence of O-H) indicates the presence of carboxylic acid (COOH).
In this graph there is a peak at 3248 cm-1 (C-O) and a peak at 1589 cm-1 (O-H) which confirms the presence of carboxylic acid.
To confirm the presence of amides, a medium absorption near 3400 cm-1 should be observed which is the case in this graph.
Absorptions in the region of 1450 to 1600 cm-1 often designate an aromatic ring and when consulting the C-H region we can confirm its aromatic since the peak is to the left of the 3000 cm-1.
Nitro groups give two strong absorptions at 1530-1600 cm-1 and 1300-1390 cm-1.

H NMR spectrum
Nuclei tend to be deshielded by groups which withdraw electron density. Deshielded nuclei resonate at higher δ values, whereas shielded nuclei resonate at lower δ values.Examples of electron withdrawing substituents are -OH, -OCOR, -OR, -NO2 and halogens.

We began this experiment by weighing out the known values of mass for 1-chloro-2,4-dinitrobenzene and m-aminobenzoic acid which was 1.012g and 0.686g respectively. These values were calculated before the experiement based on the mole ratios of the balanced equation in question. Here the reaction was a 1:1 ratio so we were able to determine the theoretical mass of our product, m-(2,4-dinitroanilino)