ORGANIC CHEM LAB
ORGANIC CHEM LAB CHEM 2364
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This 2 page Class Notes was uploaded by Malcolm Glover on Tuesday October 13, 2015. The Class Notes belongs to CHEM 2364 at Louisiana State University taught by Staff in Fall. Since its upload, it has received 18 views. For similar materials see /class/223113/chem-2364-louisiana-state-university in Chemistry at Louisiana State University.
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Date Created: 10/13/15
Chem 2364 Synthesis ofp nitroaniline pnitroaniline is an important chemical for the synthesis of dyes Its synthesis involves an electrophilic aromatic substitution EAS This type of reaction is very important in synthetic organic chemistry An electrophile and an aromatic ring are the principal actors a catalyst is o en needed When an EAS is performed on benzene it s relatively easy to predict the product However when the aromatic ring has substituents different isomers can be obtained As a general rule if the substituent is an electron donating group EDG it will favor EAS and will orient it to the o and 2 positions On the other hand if the susbtituent is an electron withdrawing group EWG it will hinder EAS If more than one substituent is present the one that wants EAS the most is the one that will govern the reaction For example if the aromatic ring has an EDG and an EWG the one that will govern orientation is the EDG because it favors the reaction Le wants the reaction to occur In the case of the synthesis of p nitroaniline one could think that since the amino NH2 group is already an EDG a simple EAS with the appropriate electrophile would give the product However the electrophile needs acid to be generated and this protonates the amino group The protonation of the amino group yields an ammonium group NH3 which is an EWG For this reason is that the reaction is carried out in three steps lst Protection of the amino group synthesis of acetanilide 2quotd EAS between the protected amino group and nitronium ion synthesis of p nitroacetanilide 3rd Deprotection ofthe amino group 39 J 39 39J 39 of quot quot39 gt p quot quot39 The protection of the amino group with acetic anhydride yields acetanilide which is still an activating group but since it s neutral it does not get protonated Protection 7 o Nye 13 g ed dwr Chem 2364 EAS nitration o O 9 OzN QNHCO S OH gt OzN CgH O S OH o 1 ll Electroph e NHCOCH3 gt 63 a NHCOCH3 CNHCOCH3 CNHCOCH3 NHCOCHa NHCOCH3 E 363 E j E j o N N N 90 OH N N o oe o iquotoe o oe 09 0e 0 oe o NHCOCH3 N e OO ES
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