nitration of benzene mechanism pdf

Nitration of Benzene. stream � �l~���.�r~��܎��+L“�!��i{��AA^���RW^�v���k�+����B�bޏ�ho�=�b��MC)�]�*�P�t\G��v9������9�)�{�3o�6�F7{W]x '�#�]+�5����y��E8�xa��E�N? 4. �/�Jơ��z�r�4��R[h3�$ �mT�Be�Fy[c�Jq���j(�mT�~*լ��)T�A�*Ռ�2�)u��)O��H~�}��x��H��a�멞�(nV�XT5�d�֜�:����M���Z�W#& :E�&�ri�6��{t�x�P�M�u� <>/ProcSet[/PDF/Text/ImageB/ImageC/ImageI] >>/MediaBox[ 0 0 720 540] /Contents 4 0 R/Group<>/Tabs/S/StructParents 0>> 6 0 obj <> <> 0000006236 00000 n 0000006492 00000 n 2 0 obj 0000001105 00000 n endobj �?�߇m{*��a�����^֤����������)M���^����j1�x=�9ڥ~�o�S�������E�)x!%j�a�&�Q�wZG �. <>/XObject<>/ExtGState<>/ProcSet[/PDF/Text/ImageB/ImageC/ImageI] >>/MediaBox[ 0 0 720 540] /Contents 15 0 R/Group<>/Tabs/S/StructParents 1>> x��W��1�G�p���S �!6C� ��)��q{|ì�%�����nw��\���$Y�g]^��HQ|� �x�.�������FZ��m]�H��0J:��u]>�ˇ� ��+e��2���L���){+���%��Z��A%�?�3���q(��u��b��72�r$� endobj Overall transformation : Ar-H to Ar-NO 2 Reagent : for benzene, HNO 3 in H 2 SO 4 / heat; Electrophilic species : the nitronium ion (i.e. ����.�� Q6�-A�J�%�[>nb-{8Q�s�>�~V�- �P+�7wB���T-@s�RV��j��׎Q�)~a���s��|������.��ܽ��<9�G���ja�_����KcF�]��gR;� ���H]`1�6�s~�-�Vvn6+9Ha��jt� D�G@h�DtL�r��7�����c�X�Mc�rXG�x�O��?�u�ш6�r�v����?7&���E͙3Ƚ"�1�U1H�������?+�S����F�C:ZL_�X,�+�ȡ�p)d%�� 3. endobj x��X�n�F}�ا���^�K4 `�I� ��E$yP�V"[.M�p��g�ԅ%ʒ��.wwf�Μ�!�`/^�OoO�x����?ݎ`�!�R�1��F��.�kD"���EϺ�?���t�ؒ �$ l�©�� ���N��dR��iL2���ίI��śn�S4�mt'Q�ltk���U��f�v���yu��_��\+�,��TB�Y�{9�{&*r2sX��gK��vX,�rxQ��+屔�l�e&N�鿸��b���a�-myG�A�K»x2tU��? Summary. 7 0 obj 13 0 obj 9 0 obj The rest is according to the general mechanism of electrophilic aromatic substitution: The mechanism is the same regardless of the electrophile. Generation of electrophile 0000002739 00000 n The electrophilic substitution reaction of benzene is done with the help of three steps. It As the NO 2 + ion approaches the delocalised electrons in the benzene, those electrons are strongly attracted towards the positive charge.. Two electrons from the delocalised system are used to form a new bond with the NO 2 + ion. xref 0000002984 00000 n endobj <> *���*��>���E1���?����������v������i�反Ť�Y���#H�[7O5�����_�Sx�P�Ī��7M�Q�Oo�Ɠ1�����(�^�R��c��qqO�[lѕ-�+�o���:2�)3�̠`���p��5e��`$7��aRʤ4��q������̳��uM2l%���L:vy�2�m}"���L�����O�b(v2e q!|M�d�~2�R�2�\A��vScL�����lW��8uϕ�`�Ҷ�$���kN��� �'�Kb�����s/*�(xy����܇��\&��J6���� �ϱGvu˞�T;�R�}��@�w3�����w\�j �������w�� N-4����oz��܇-���V�(Åe�*\�*c��b��,���!~'��E�1��E�K��ilh��݌����MT�t����5��ڹ� `3mSܥ�D�_�;��9ؗ4$AL5e�M��ޣO��H~�۠j���p�iT��d�$VX�ev�+y2��n�\�.7��fd�:�l���h6��Z~4�#Waw����2�ID�4]cB9g���8��M����� �^`��&$ 7�Ë�VܱX��h����,�]_퓊�Jm��X���X�����(Nb�M?b�FL�Z=���q���h7���9 �cJ7�a��a�'����;�~Q�|u�� �U�{;)�ۯ������t��w�U)p5��j�� ��x۽˥ <> trailer 0000000676 00000 n endobj 0000001446 00000 n ��?�,q�%ح��u4sY�٧n�4�㫟y1�?g���S��6[ķ����%���ri�۔2�xd����/��k�c�%����C����Q�upI��Tֽ#̀����P�>Gk��.Ryer�*7��Un�1��1N�D�%{! <> <>>> 8 0 obj 15 0 obj H��W[s�~ׯ�Kg�Ԣq�Ǹ�n3��N�3y�恖�b�����U��� ^D�N���8��������,��_���K&���B��{#�B2�s��{�{���-n��� ���۫�f�_�x�9���B�\8Ȼ���)���_˕�eƞ�����ۯ_����x*����y�o*������,�V"W��;>!����-�Y�e�Y��p�������d Consider the nitration of benzene versus the nitration of trifluoromethylbenzene and toluene (methylbenzene). <>/Font<>>>/BBox[ 0 0 203.73 34.772] /Matrix[ 0.35341 0 0 2.0707 0 0] /Filter/FlateDecode/Length 971>> 88 0 obj<>stream 0000006873 00000 n endobj Stage one. endstream endobj 87 0 obj<> endobj 89 0 obj[90 0 R] endobj 90 0 obj<>>> endobj 91 0 obj<> endobj 92 0 obj<>/Font<>/ProcSet[/PDF/Text]/ExtGState<>>> endobj 93 0 obj<> endobj 94 0 obj<> endobj 95 0 obj[/ICCBased 104 0 R] endobj 96 0 obj<> endobj 97 0 obj<> endobj 98 0 obj<> endobj 99 0 obj<>stream 5 0 obj <> Both π and σ transition states on the potential energy surface of the nitration of benzene with nitronium ion have been successfully optimized using unrestricted hybrid DFT procedure B3LYP with the triple-zeta 6-311G ** basis set without any 0000000994 00000 n %���� Figure 1: The mechanism for the formation of a nitronium ion. 1ƻJ&���B������0��^ыkM�xs�(Ҙ�b�}7�CrO�Z���!A1�ԙ�vt���p�"4$$#�E�BB~���D� ���B��͸�d�^ ����_GQ�T2�W��D�5 ۆG \J�ZH�5�q-j3`�d�M[:��Sq;J+l�~q���UQ 2�F\�,C�7 ��0�e�{��ZR�h2vJ�B��pCWE� _�,���*}��Q:i|�k� ��z!֖�R�PPA1t4�w�҅9�]b�a�v�ḋ z��.�4����X֮�U�. <> Toluene undergoes nitration to give ortho and para nitrotoluene isomers, but if heated it can give 0000003060 00000 n NO 2 +) formed by the loss of water from the nitric acid [ 11 0 R] '� ���-9B�Ew���c���W��o9����?Nƨq�#MS�f8�y�6��7�cf����`䠟���Yq�K�>�o�L��J�!���F��X*8H��%�3��6�\7ov�ȲsRǔ�2�Ҭ�@�|B��`���h�Q�L��XA���E�\����c�TΤ�������5C쮆(Լ!C�T��+��p�^�W�N��t=����'���,.M�w��!q(|��1� <<37bb534c43bd8a4aaf87a275c05355b0>]>> ��5Z|��$�u���=M���h�Qȟf�h}�̻�/�m]$I6Iw� B׬��a�a��h�\��+�ؑ��ۑ�,C��QF���*�S�bt�C?M�|��N�? 10 0 obj Reaction type: Electrophilic Aromatic Substitution. endobj (�v��{"} �=� �~_9����zf��#�(P�Ȗ�ts�|��YKN��'^"/��E�^:� =qc�_�y�re1�f�^d#^��V�~��iYǼ�鐝�O�.���Vw�?���`��q0Q�w������ 4)[Џ���n�s�:������L3H������JV4dh���s ns�oѦ�I��n4 %PDF-1.5 0000002027 00000 n <> endstream 0000001301 00000 n endobj startxref 1003 Nitration of benzaldehyde to 3-nitrobenzaldehyde Classification Reaction types and substance classes electrophilic substitution of aromatics, nitration of aromatics aromatics, nitroaromatics, aldehyde Work methods stirring with magnetic stir bar, extracting, shaking out, recrystallizing, filtering, use of … 0000002500 00000 n %PDF-1.4 %���� endobj endobj x��X�o�FG����>�e���"�@�*��)U����BH�J0u��r}g�6���B�ò�����o>vt����epy�׃�� �n�8p�9R�"��h������-KnW�Ft�����݂�/�� Q�Y�d�AB�nu/ �{��@�b��O�����v�&�&��6��v��V~���v�|��_�qLI�,�s(!�l����d)�9�f4%���9ڎ�?����P� ��w=.���8�ϰ#�ۣ_!���Tϸ �W���x ����+�c������0�!���Z��͹� 1 0 obj }C��JhdT�D�\�~@���XZ/�s9�[�+>L�ǔ��Lo ��� � {�u"�I�3r�{7=͢�xG����7믧$}�ϾZ�u��!�]#��T�+L�Gy$�Ö�Z� ����6F^Y��Y��"�1�u۞�V�|%�ݲ֔�y�����p��@��v��Yʩq}�LR�"��[-ߪ�o���K�����L�%�=b������� (�rng3%���?�M{:ǂ��A#�z�.� 16 0 obj :� ��sCBpoZ��%6���������\��W����(1꯱��3�>�{j�B3�'�cꖩY'9�$)].�q�>�+ϱwl�+���!�57�]mF��9x� @��9,aFֻh�mA� �z:W;���܎�*5u��ù}��\�OE���Ƒ�G���5@w�9Y=| ��8��Q��24���su87�C��n6g���>�g�T�b��N�%��>i�4��zې���Tƌ�[�Ȑ7�9�r���՝�͖Б��֏e[��ÉmN/���&@�:��W� ���J�L��r��x8T���7�BL\b��+�ͺ���n���A�sM]lj����]$���_�#�M�бJ����좶Rq�#�C=QG#�,�6�]���ؓJ��C�}+ a6o�_ ����Z2=���P#�CRB���0/6h+ HU{k��ɓPk�߆�oC�7��m5��Vה�tوZ�/V�d��B�=�����@6{�5 ]�$3\�E��ŸB�X��Z�ہҏ~�� (Cm�6�t;L�ɫ�Y+}�+dH��N�W6��H�(߭X��%�� ;N����@�T7��3�A�T۠���D�_���mXP>h��U�,� 0000000016 00000 n <> endobj <> 3 0 obj 14 0 obj 0000001129 00000 n <> AlCl 3 R Cl O R O 2. 86 0 obj <> endobj %%EOF 0000002465 00000 n Friedel-Crafts Alkylation R = alkyl; X = Cl,Br, Catalyst = AlCl 3, etc. The electrophile in the nitration of benzene is the + NO 2 (the nitronium ion), which is formed by protonation of HNO 3 by H 2 SO 4 (yep, sulfuric acid is powerful). 0000007095 00000 n We see that the trifluoromethylbenzene reacts much, much slower (4 x 104 times slower) than benzene. 1. stream V���_�!�%��6$ѿ6�� endobj The methyl group of toluene makes it around 25 times more reactive than benzene in electrophilic aromatic substitution reactions. Nitration General Reaction Mechanism E E (1) H E E H (2) + H+ Ca ta lys t R X R 1. Electrophile will attack the Benzene ring. ��o:~#Q�~&�쇢1�x�I�j�X�1���M�&�c��V�Վg�(�/��Q*��i��aLT���:��(S҅ܲ-Em�L��DuِGlM`CV��|. L/���)>o�%�V�c�:A@���rH�w��ۻƲ�O�@�>�}X�=*�����W@���~��� ��l!P����Ⅵ�n!�_ݺ^|���N����D��D�7�F�ڷEX\^~�f��=��"��d��g���N� 86 19 0 Diprotonation. endobj ]�,�\���w��oik #���_�,~�ϟX2������� �? stream endobj 2. �l�;ԟ����j4���/���y1F� n}��y{�U�v�\' �:��1U�!�0y�k�NU��W�g��� �����c����#3{̂Y �N�"N���:E����*��D���6��[>;��Uˎ��iΧ.��w��ZE�eMm���n��'���f,�ӡ-;�u~��´i;����x@�:�bSKjY�_�4`�����`$�j���� DAG�{�k�DL���=ׁߞ��Ӿ:��$� 1. The mechanism for nitration of benzene is in three steps. endobj Nitration of Benzene. endstream 4 0 obj diFш��XhGGD��n��:�q� bI�#$xX\b�(�V��p������C ��Sa�3�gy�߸�)A�a��@3��iE�97�t c�2 ��� ��A� 12 0 obj 11 0 obj ��P��Ol)���Lrn� �����dқ\h�U�y����6A�!�:E�B�rQ�%9)���2ɉSAF :!��6A��M�]]6��q���#��%��{)+��1�~��^���.���U�yi_�P����� k�M[��[�e�i��(��"�ha�&�lp ��M��A1��j����v�l�s�%o�܋�E0�+v0�Ds#���a�,�t�p�ܰ}���R���ΎA�d�(#�����vT��f\@��H�qY���J��i�e.%�E1���`U�I��������vU�����y+m�)i��( I:-���a_��d�F���ʾ쫖r���{��f�G�S��"���ù�a�j}z,�z�{�$��Y?M"�>j���l�B�� V�! 0000005920 00000 n x�b```"a~���1�%�cNI��'��ѝ��sf������b�e:�"��x��e�q%��@Vp���-O����f�sV$Od�>S�v���&%�F! Nitration of benzene mechanism. 0000001172 00000 n Generation of electrophile. The electrophilic substitution mechanism.

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