Relative Reactivity of Anilines :: essays research papers

Relative Reactivity of AnilinesAbstract Various Anilines were tested with Br2/HBr solution, the merchandises were crystalise and thaw points attained to verify relative reactivity. My assignment, 2,4-Dibromoanisol, was prepared in a yield of 52% with a melting point of 55-58 C . reactionMechanismProcedure Anisole (0.35mL, 0.0378mol) was obtained and set(p) in a pre-weighed 25 mL circular bottom flask, along with 2.5 mL of glacial acetic paneling and a magnetic stir bar. Then the reaction apparatus was assembled, the prohibitionist tube was charged with conc. sodium bi sulfate, the 25 mL round bottom was attached to the apparatus, and 5 mL of Br2/HBr mixture was obtained and fit(p) in the round bottom. The reaction took place for 20 minutes. An orange liquid was obtained and placed in a 125 mL Erlenmeyer flask along with 25 mL of water and 2.5 mL of conc. Sodium bisulfate soln. The solution was then placed in an ice bath to precipitate and then the solid crop was filter in a Buchner funnel. These crystals were then re-dissolved minimum amount of virulent solvent (heptane) and recrystallized. Once a dry product was obtained, a melting point was established (2,4-Dibromoanisol mp 55-58 C) and percent yield was established (52%). Results by a melting point reading, it was determined that the product obtained was 2,4-Dibromoanisol mp 55-58 C. The products obtained by my partners, were determined to be (p-bromoacetanilide mp 160-165 C) and (2,4,6 tribromoaniline, mp of 108-110 C) respectively. Discussion and Conclusions Interpreting these results convey concluded that relative reactivity of these three anilines in order of to the highest degree re dynamical to least reactive go Aniline Anisole Acetanilide. Aniline, has an NH2 , the most active substituent , and adds to any ortho/para position available on the ring. This data is corroborate with the product obtained, (2,4,6 tribromoaniline, mp of 108-110 C). As for anisole, it has a strongly activating sort out attached, OMe an alkoxy group, and it added in two of the three available spots, both ortho. The results conclude (2,4-Dibromoanisol mp 55-58 C ). Acetanilide has a strong activating group attached, acylamino group, tho this group is large and the ortho positions are somewhat hindered so the majority of the product obtained added at the para position, results conclude (p-bromoacetanilide mp 160-165 C). Since all the substituents attached to the remindful rings were activators the only products able to be obtained were ortho/para products.