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Synthesis of a Bromonitro aniline

Synthesis of a Bromonitro aniline - Synthesis of a...

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Synthesis of a Bromonitroaniline David Grauer Jimin Kim Tuesday Lab
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Purpose: We wanted to synthesize Bromonitroaniline from aniline. We also sought to determine the predominant isomer formed using melting point analysis. Procedure: Starting with aniline, we produced an acetanilide, then attached bromine, and finally nitrated the bromoacetanilide with nitric and sulfuric acid. The acetate was removed to give the bromoacetaniline. Observations: Masses: Product B = 506 mg, Product C = 215 mg. (forgot to mass product A) Melting Point Data (Benzoic Acid, 120-122.5ºC): Compound Melting Point (ºC) 2 (solid, white powder) 109.5-111 A (orange solid, dentritic crystals) 159-162 B (yellow solid, dendritic crystals) 103-106 C (orange solid, dendritic crystals) 109.5-110 TLC Data Below
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Discussion: 1. (ppm = 3.6, S, H=2), (ppm = 6.7, D, Jbd=7.91, H=2), (ppm = 6.78, T, Jcd= 7.25, H = 1), (ppm = 7.18, T, Jbc=7.91, Jcd = 7.25, H=2). 2. a. MP = 109.5-111ºC. This is slightly lower than the CRC Handbook’s value of 114.3ºC. b. (ppm = 2.15, S, H=3) , (ppm = 7.1, T, Jbc= 7.25, H=1), (ppm = 7.2, T, Jcd = 7.91, Jcb = 7.25, H=2), (ppm = 7.5, D, Jbc = 7.25, H=2), (ppm = 8.5, S, H=1) 3. a. MP = 159-162ºC. This is the para isomer. The literature (CRC) MP is 168ºC (p), 87.5 (m), and 99 (o). b. (ppm = 2.1, S, H=3), (ppm = 7.34, D, Jcb = 8.57, H=2), (ppm = 7.43, D, Jcb = 9.23, H=2), (ppm = 8.7, S, H=1) c. Although A did not travel very far (Rf = .05), there was only a single spot, so it was pure. d. I neglected to weigh Product A, so I am unable to report a percent yield. It was assumed that the reaction was quite efficient given that not much PyHBr 3 was used. This was justified by the fact that there was not much PyHB 3 left over (the solution was not very orange). 4. a. MP = 103-106ºC. According to the literature, I isolated 4-bromo-2- nitroacteanilide which has a MP of 104ºC. The other possible isomer has a MP of 132ºC.
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b. (ppm = 2.3, S, H=3), (ppm = 7.73, D of D, Jbc = 2.64, Jbd = 6.59, H=1),
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