Bromination Lab Report

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Bromination is a type of electrophilic aromatic substitution reaction where one hydrogen atom of benzene or benzene derivative is replaced by bromine due to an electrophilic attack on the benzene ring. The purpose of this experiment is to undergo bromination reaction of acetanilide and aniline to form 4-bromoacetanilide and 2,4,6-tribromoaniline respectively. Since -NHCOCH3 of acetanilide and -NH2 of aniline are electron donating groups, they are ortho/para directors due to resonance stabilized structure. Even though the electron donating groups activate the benzene ring, their reactivities are different and result in the formation of different products during bromination. In acetanilide, the lone pair of the nitrogen is delocalized into the…show more content…
Then percent yield was calculated to be 67.57%. The isolation of less product resulted from using less amount of acetanilide than 0.07g at the beginning of the experiment. In addition, the melting point of the product was measured to be 164.8-168.50c, which is in the range of the normal melting point of 4-bromoacentailide, 165-1690c. This confirmed the formation of 4-bromoacetanilide from the bromination of acetanilide. From the bromination of 0.05g aniline, 0.156g of the product was collected. The percent yield was calculated to be 88.1%. Some amount of the product was lost when transferring the product from the Buchner funnel to the balance to measure its mass. To ensure the formation of the desired product, melting point of the product was measured to be 119.8-121.90c, which is in the range of the normal melting point of 2,4,6-tribromoanilne, 120-1220c. Thus, the product was indeed…show more content…
In this experiment, it was possible to produce the major products from bromination of acetanilide and aniline. 0.075g of 4-bromoacetanilide and 0.156g of 2,4,6-tribromoanilne were collected from bromination of 0.07g acetanilide and 0.05g aniline with the percent yield of 67.57% and 88.1% respectively. At the end of the experiment, to prove the formation of the major products, melting point of the products were measured. The melting point of the product from the bromination of acetanilide was 164.8-168.50c, which is in the range of the melting point of 4-bromoacetanilide, 165-1690c, as reported on the Chemical Book, CAS Database List (chemicalbook.com). The melting point of the product from the bromination of aniline was 119.8-121.90c, which is in the range of the melting point of 2,4,6-tribromoaniline, 120-1220c, as indicated on PubChem, Open Chemistry Database (pubchem.ncbi.nlm.nih.gov). This verified the formation of the major products. Overall, one can say that the experiment was

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