Notes0630 - Experiment 7: Synthesis of p-Nitroaniline from...

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Experiment 7: Synthesis of p-Nitroaniline from Aniline Synthetic Scheme: NH 2 NHCCH 3 O NHCCH 3 O NO 2 NH 2 NO 2 CH 3 COCCH 3 O O CH 3 CONa O HNO 3 H 2 SO 4 1) HCl, H 2 O, heat 2) NH 4 OH, H 2 O Aniline Acetanilide p-Nitroacetanilide p-Nitroaniline Acylation Nitration Hydrolysis A) Acylation of Aniline (Protection) Protecting groups - A sensitive functional group is protected by transforming it to a derivative that withstands the reaction conditions while another part of the molecule (unprotected) will undergo the desired transformation. NH 2 NH 3 OSOH O O H OSOH O O NH 2 strong activator ortho, para director NH 3 + strong deactivator meta director 35
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Basic NHCCH 3 moderate activator ortho, para director O NH 2 NHCCH 3 O CH 3 COCCH 3 O O CH 3 CONa O Aniline Acetanilide Acylation Mechanism: NH 2 CH 3 COCCH 3 O O OCCH 3 O CH 3 C O NH 2 NHCCH 3 O H NHCCH 3 O CH 3 CO O B) Nitration of Acetanilide Nitration p-Nitroacetanilide Acetanilide H 2 SO 4 HNO 3 NHCCH 3 O NO 2 NHCCH 3 O NHCCH
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This note was uploaded on 06/24/2009 for the course CHEM chem 2364 taught by Professor Davila during the Spring '09 term at LSU.

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Notes0630 - Experiment 7: Synthesis of p-Nitroaniline from...

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