Introduction to Organic Chemistry Essay

Amines are confuseds composed of newton atoms presence alkyl or redolent compounds. Amines undergo interesting responses, wiz of which is with the reply with nitrous acid producing an azo spot. In this get word, the investigate cogitate on synthesizing an observing the physical properties of Sudan-1. Sudan-1 is of the roughly gross tints found in waxes, oils and in some feed ing lossients specifically curry and chilli powder.Furthermore, this study aimed to understand the mechanism behind the synthesis of 1-phenylazo-2-naphtol. To be subject to synthesize Sudan-1, preparation of phenyldiazonium chloride dissolvent and - naphthol solution were do. Ingrain dyeing was also done in this audition. The synthesis of Sudan-1 has a two-step reception diazotization and coupling replys. Diazotization is the governance of diazonium season, meanwhile, the coupling reaction took place when an worked up aromatic compound, -naphtol was reacted with the diazonium salt, ben zene diazonium chloride, to variance the azo compound cognize as the 1-phenylazo-2-naphthol. As a result, an orange-red effectuate was formed after series of reaction. Hence, all the said objectives in this experiment were achieved.Amines are compounds that are composed of a nitrogen atom bea bring forward alkyl or aromatic assorts. They are basic and nucleophilic because of their lone pair. They choke both in plants and animals. Amines pay offs some of the virtually interesting effects and of the common reaction of aminewith nitrous acid producing a dye4. Alizarin, for example is a red dye extracted from madder root used by Egyptians and Persians. However, in this experiment, it aimed to produce a dye commonly known as Sudan-1. Sudan-1 is a lysochrome with the chemic formula 1-phenylazo-2-naphthol. It is a powdered substance with an orange-red people of colour.This azo dye is most commonly found in waxes, oils, and also in some food coloring ingredients curry powder and c hili powder. However, the presence of Sudan-1 in most foods now is currently being banned because it has been classified to be carcinogenic. This experiment focused on synthesizing of 1-phenylazo-2-naphthol which is a two-step reaction. The first reaction is the reaction of aniline with nitrous acid, which is called diazotization and second, the reaction of diazonium salt and beta-naphtol to form azo dye which is the coupling reaction.Figure 1 Diazotization reception of Aniline to Produce a Diazonium Salt Figure 1 Diazotization Reaction of Aniline to Produce a Diazonium Salt In diazotization reaction, there is a formation of diazonium salts. This reaction is do possible when a old aromatic amine is treated with nitrous acid. Then in coupling reaction, the electrophilic substitution reaction of a diazonium salt with an activated aromatic ring formed a azo compound specifically an azo dye.3 The main objective of this study was to be able to synthesize Sudan-1. Also, it aimed to cha racterize the azo dye with its most distinguishing physical properties. Furthermore, this experiment also aimed to understand the mechanism behind the synthesis of Sudan-1.Figure 2 Coupling Reaction of Benzene Diazonium Chloride with -Naphthol Figure 2 Coupling Reaction of Benzene Diazonium Chloride with -Naphthol Aniline was reacted NaNO2 crystals under acidic condition using HCl in a cold temperature. The solution was done in a in truth cold temperature because the phenyldiazonium intermediate easily decomposes back to its aniline counterpart at a slightly high temperature hence the temperature of the solution was maintained in an ice bath beneath 5C.Rock salt whitethorn also be added to the ice bath to maintain the temperature. However, in this experiment, no rock salts were added instead constant monitoring of the temperature was done. -naphthol solution was used as a coupling reagent in synthesizing Sudan-1. In preparing -naphthol solution, -naphthol was dissolved in 5% of a queous NaOH and was also cooled in an ice bath under 5C, this was to avoid the decomposition of the compounds. The main reaction that occurred in the preparation of phenyldiazonium chloride solution was diazotization reaction. Diazotization is the reaction between a primary aromatic amine and nitrous acid at cold temperatures to diazonium salt compound.2 Figure 1 beneath is the reaction exhibited by the phenyldiazonium chloride solution.As this experiment aimed to synthesize Sudan-1, two stairs are done. The first step would be the reaction of a primary aromatic amine to produce a diazonium salt as seen in Figure 1. The second step, then, is the reaction of the diazonium salt with a strongly activated aromatic syste,l known as coupling reactions. Azo coupling is the reaction between a diazonium compound and aniline, phenol or other aromatic compound which produces an azo compound.5 In this experiment -naphthol couples with the diazonium salt. Figure 2 below shows the coupling reac tion of the benzene diazonium chloride with -naphthol and having the product of Sudan-1. Furthermore, judge 3 below is the summary of reactions of the synthesis of Sudan-1 in this experiment. Figure 3 Summary of Reactions in Synthesizing Sudan-1Figure 3 Summary of Reactions in Synthesizing Sudan-1In this experiment, a interpenetrate paper was used to undergo ingrain dyeing. Ingrain dyeing is an irreversible chemical reaction of the diazonium salt solution and the activating aromatic solution. An orange-red sift paper was produced after such procedure. The presence of orange-red color in extend indicates the presence of the azo dye (see appendix for the orange-red filter paper produced). The Sudan dye is synthesized right in the spaces between the filter paper such that they are permanently trapped inside the fiber spaces of the filter paper.2 later on miscellany the phenyldiazonium chloride solution with the -naphthol solution, an orange-red paste-like solution was formed. Furth ermore, the mixed solution was also reacted at a temperature not exceeding 4C for 1-5 minutes. Afterwards, the mixture was also filtered was washed with several portions of water to filter the product, Sudan-1.Recrystallization was also done when the filtrate was pissed off bath after dissolving it with 95% hot ethanol. AS a result, orange-red crystals were formed which is the Sudan-1 product. The crystal appeared to be orange-red in color due to the N=N connect present in Sudan-1. The N=N is trusty for the absorption oflight thus reflecting a color which is orange-red. The structure of Sudan-1 is shown in Figure 4 below showing the N=N bond of the compound. The N=N is known as the chromophores which are responsible for the color. The OH meeting attached in the structure is also responsible for enhancing the orange-red color. The OH functional group is known as the auxochrome, which modifies the ability of the chromophore to absorb the light.1Figure 4 body structure of Sudan-1A zo-compounds, compounds with general formula Ar-N+=N-Ar-, are coupling products from the reaction of diazonium salts with amines. The general reaction pattern for Sudan synthesis first undergoes diazotization reaction and then coupling reaction with highly activated aromatic compounds. In this experiment, the diazotization reaction of aniline with NaNO2 and HCl yielded a diazonium salt, benzene diazonium chloride. Furthermore, the diazonium salt then underwent coupling reactions with an activated aromatic ring which is -naphthol.The coupling reaction yielded an azo compound which is most commonly known as the Sudan-1 with an IUPAC name of 1-phenylazo-2-naphthol. As a result of the reactions in this experiment, an orange-red color of solution was produced. This experiment aimed to understand the reactions that underwent to synthesize Sudan-1 as a result, figure 3 was the summary of reactions. As a physical result, orange-red colored crystals were produced representing the azo compoun d, Sudan-1. However, some minor errors go forth not be ignored in this experiment.Some errors like human errors might have affected the results in yielding a pure azo compound. One human error, would be the measuring of the reagents used to yield the said product. Also, the misreading of some measurements may have also affected the results of this experiment. Also, some impurities in the chemicals used will also not be ignore, since this impurities may have led to a not so visible side reactions in the said experiment. After being said and done, all the said objectives in this experiment were met.