Electrophilic Aromatic Substitution Lab Report

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The purpose of this experiment is to examine the reactivity of different compounds. To accomplish this, different types of benzene (aniline, acetanilide, phenol, or anisole) will be brominated.  The reactivity and activation strength will determine of the compound is polyhalogenated, or monohalogenated. In this experiment it is to be predicted in which order the reaction substitution(s) will occur and the reactivity order of each of the benzene compounds.  The product will then be analyzed and identified by recrystalling and comparing the melting point of isolated product to literature values. Electrophilic aromatic substitution (EAS) is the introduction of a functional group to a benzene ring. In the reaction, a …show more content…

The hypothesis expected that aniline and phenol would be tri-substituted, and anisole an acetanilide would be mono-substituted and have a bromine in the para position, because the para position is favored over the ortho position because of sterics. Results after the experiment were: phenol > aniline > acetanilide. Anisole was not applicable because the experiment was not ran during class and that data was not provided. The results for aniline were one group claiming 2,6 dibromoaniline and two groups claiming 2,4 dibromoanaline. 2,4 dibromoanaline seems more probable because it is preferred to have substituents spaced out on an aromatic ring, for less tension between substrates. The conclusion with phenol was that it was trisubstituted 2,4,6 tribromophenol. Although there are two melting points, it is the same product that was being analyzed, because only one group could correctly brominate phenol. The temperature difference is attributed to two different mel-temps being used, causing two different temperatures. The results for acetanilide, were that all three groups concluded that 4-bromoacetanailde was the product. This is predictable because acetanailde is a bulky substrate. Compounds favor that bulky substituents only attach in the para

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