nitration of phenol mechanism

/R5 14 0 R /Subtype/Image Phenol reacts 1000 times faster than benzene. This means that the ortho and para benzenonium ions must be much less unstable that the meta one. (�� /Type/Encoding >> Nitration takes place almost exclusively on ortho-para positions. /Subtype/Form 0000002719 00000 n That experimental fact suggests that benzene reaction pathway has to be the highest. With concentrated nitric acid. �� � w !1AQaq"2�B���� #3R�br� endobj 39 0 obj << /Linearized 1 /O 41 /H [ 864 266 ] /L 35851 /E 7294 /N 7 /T 34953 >> endobj xref 39 19 0000000016 00000 n The electron lone pairs of oxygen delocalizes towards the ring and increases electron density at ortho and para positions. 10 0 obj /Length 65 The results of studying this mechanism at the G3(MP2)//B3-CEP level pointed to the occurrence of a /ColorSpace/DeviceRGB << 0000002519 00000 n (�� Two different mechanisms have been proposed for the nitration of tyrosine. The oxygen is thus able to further delocalize the positive charge by sharing its electron lone pairs. Therefore, the resonance hybrid is described with four resonance forms. 0000003893 00000 n c) and could there be any other biproducts in this reaction. p� The OH group activates the aromatic ring in SEAr and lowers the activation energy. endobj ���� Adobe d �� C Selective and eco-friendly nitration of phenols. Entry Substrates Products Time(h) Yields(%)a 1 Phenol o-nitro phenol 6 75 2 4-nitro phenol 2,4-dinitro phenol 6 98 3 4-bromo phenol (�� (�� (�� stream (�� (�� Experimentally, the ratio ortho-para is 40:58 but there are two equivalent ortho positions. 0000004558 00000 n This means that the ortho and para benzenonium ions must be much less unstable that the meta one. For this purpose, 6.2 eq of [Msim]Cl and 2 eq of NaNO2 were reacted with 1 eq of p-methoxyphenol. (�� Nitration of phenol as a special case has been studied using various nitrating agents under different conditions [4-22]. (�� Reaction: Phenol + HNO3 --> 2-nitrophenol + 4-nitrophenol. >> (�� /Height 619 3) Direction of substitution 0000001817 00000 n 0000004764 00000 n G3(MP2)//B3-CEP theory was applied to study the mechanism of phenol nitration in the gas phase, as promoted by the electrophile NO2 (+). /FormType 1 Therefore, the para position reacts 58/20 times as fast as the ortho, i.e. /Resources<< The resonace forms of each ion give us the answer. Therefore, the resonance hybrid is described with only three resonance forms and is more unstable than the preceding cases. ��(�� /ExtGState 11 0 R (�� (�� >> $, !$4.763.22:ASF:=N>22HbINVX]^]8EfmeZlS[]Y�� C**Y;2;YYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYY�� k�" �� 0000000864 00000 n (�� $4�%�&'()*56789:CDEFGHIJSTUVWXYZcdefghijstuvwxyz�������������������������������������������������������������������������� ? (�� This means that the ortho and para benzenonium ions must be much less unstable that the meta one. (�� The intermediate bezenonium ion is more stable when the OH is attached to it. The energy diagram of phenol nitration is qualitatively similar to benzene's. The OH group activates the aromatic ring in SEAr and lowers the activation energy. 0000000727 00000 n >> 0000002321 00000 n The positive charge delocalizes along the ortho and para positions. (�� Phenol reacts faster than benzene. (�� 0000003468 00000 n /Filter/FlateDecode (�����f=:;�qI��0�۰��ד�:̷�v��Z�ڍ���i��\��"Fg�I@Ģ�\ /BitsPerComponent 8 Nitration takes place almost exclusively on ortho-para positions. 11 0 obj endobj /ProcSet[/PDF/ImageC] 0000007065 00000 n (�� H��W�r���+�$'"M��C�&�ɸ'�v�X���DB&�$��Ú�"ߞ{��iu&�*�s�=��]]m��P�ݯ(#��O��)�R�%Q��QL����c���7K"���_)y�WAF�5�*"������k?��ē�8�|�{�?o�+����q�mƭ��cp����H� 0000003277 00000 n They involve the formation of (i) the nitronium ion 24 or (ii) the nitrogen dioxide radical. The reasoning is similar to that used for the ortho position. The intermediate bezenonium ion is more stable when the OH is attached to it. trailer << /Size 58 /Info 37 0 R /Root 40 0 R /Prev 34943 /ID[] >> startxref 0 %%EOF 40 0 obj << /Type /Catalog /Pages 38 0 R /Outlines 24 0 R /OpenAction [ 41 0 R /XYZ null null null ] /PageMode /UseNone >> endobj 56 0 obj << /S 140 /O 197 /Filter /FlateDecode /Length 57 0 R >> stream

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