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Nitration of Acetanilide - Nitration of Acetanilide Michael...

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Nitration of Acetanilide Michael Lester, Raymond Oldham, Audrey Paulzak CH 238 – QZ
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Introduction In order to form nitroanaline, the substituted benzene ring of acetanilide must undergo nitration and then be hydrolyzed. Many aromatic rings can be reacted with electrophilic reagents by substitution, and can nitrated directly, but aniline must be nitrated indirectly because it is very easily oxidized 1 . The goal of this experiment is to determine, through melting point analysis, what position the directing group adopts in the major product of nitroaniline. Balanced Chemical Equation C 8 H 9 NO + HNO 3 + 2H 2 SO 4 C 8 H 8 N 2 O 3 + H 3 O + + 2 HSO 4 - C 8 H 8 N 2 O 3 + H 2 O C 6 H 6 N 2 O 2 + C 2 H 4 O 2
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Mechanism N H O CH 3 + O N + O N H O CH 3 N + O O - H + H Cl N H 2 + O CH 3 N + O O - H NH 2 N + O O - + NH 2 N + O - O May also add nitronium in ortho position. N H O CH 3 N + O O - + O + H H H N H O + CH 3 H N + O O - + O H 2 + Cl -
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N H OH O + CH 3 H H N + O - O + O H H N H OH CH 3 O H N + O - O O + OH H H N H 2 + OH CH 3 O H N + O O - NH 2 N + O - O + C H 3 OH O + H NH 3 + N + O O - C H 3 OH O + N + N + O O - H H H + N + N + O O - H H H O H - NH 3 + N + O - O + O H 2 NH 4 + O H -
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Table of Reagents Amt. Used Molecular Weight (g/mol) Melting Point (°C) Density (g/mL) Acetanilide 0.502 g 135.17 113-115 Concentrated H2SO4 0.275 mL 98.08 1.84 Concentrated HNO3 0.275 mL 63.01 1.42 o -Nitroaniline 138.13 73-76 m -Nitroaniline 138.13 112-114 p -Nitroaniline 138.13 149-151 HCl 2.5 mL 36.46 -26 0.69 Ammonium Hydroxide 2.5 mL 17.03 Safety Information - Concentrated sulfuric and nitric acids are corrosive and can cause severe burns. Clean up spills quickly with lots of water, and pour any waste down the drain after diluting with plenty of water.
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