Experiment 9 examined the relative rates of electrophilic aromatic substitution. The experiment arranged compounds in order of increasing reactivity towards bromine in acetic acid. The results did not fully agree with theory possibly due to inconsistent amounts of reactants. Predictions were made for the order of reactivity for different compounds towards chlorination based on electron donating and withdrawing groups. The effect of solvent was explained as acetic acid allowing for better collisions between bromine and acetanilide due to similar intermolecular forces.
Experiment 9 examined the relative rates of electrophilic aromatic substitution. The experiment arranged compounds in order of increasing reactivity towards bromine in acetic acid. The results did not fully agree with theory possibly due to inconsistent amounts of reactants. Predictions were made for the order of reactivity for different compounds towards chlorination based on electron donating and withdrawing groups. The effect of solvent was explained as acetic acid allowing for better collisions between bromine and acetanilide due to similar intermolecular forces.
Experiment 9 examined the relative rates of electrophilic aromatic substitution. The experiment arranged compounds in order of increasing reactivity towards bromine in acetic acid. The results did not fully agree with theory possibly due to inconsistent amounts of reactants. Predictions were made for the order of reactivity for different compounds towards chlorination based on electron donating and withdrawing groups. The effect of solvent was explained as acetic acid allowing for better collisions between bromine and acetanilide due to similar intermolecular forces.
RELATIVE RATES OF ELECTROPHILIC AROMATIC SUBSTITUTION
QUESTIONS: 1. Arrange the compounds used in the experiment in order of increasing reactivity towards Br2 in CH3COOH. Explain. 2. Do your experimental results agree with the theoretical data? If not, what are the possible sources of error? 3. Predict the order of reactivity of the following compounds towards chlorination from the least reactive to the most reactive: A. Toluene, nitrobenzene, anisole, and methylbenzoate B. benzene, acetophenone, bromobenzene, and benzyl alcohol C. styrene, benzaldehyde, aniline, and iodobenzene 4. Explain the effect of solvent in the reaction of acetanilide and Br 2 in Part B. ANSWERS TO QUESTIONS: 1. The arrangement will be: nitrophenol < chlorobenzene < benzene < acetanilide< phenol < aniline because the compound having stronger EDGs (electron-donating groups) react faster while compounds with EWGs (electron-withdrawing groups) react slower. 2. The results do not agree with the theoretical data. Some possible sources of error may include inconsistent proportion of amounts of the reactants in the test tubes in the experiment. 3. a. methyl benzoate < bromobenzene < benzene < anisole b. acetophenone < iodobenzene < benzene < benzyl alcohol c. benzaldehyde < iodobenzene < styrene < aniline 4. Both Bromine and acetanilide are more soluble in the solvent acetic acid than in cyclohexane because compounds with more similar IMFA tend to have faster reaction rates as it has a better collision rate between the particles. Therefore, acetic acid is a better solvent in the reaction of acetanilide and Br 2.