nitration of benzene mechanism pdf

Nitration of benzene mechanism. 0000001301 00000 n The methyl group of toluene makes it around 25 times more reactive than benzene in electrophilic aromatic substitution reactions. stream Stage one. 1. 14 0 obj endobj <> � �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? <>>> <> Friedel-Crafts Alkylation R = alkyl; X = Cl,Br, Catalyst = AlCl 3, etc. 4 0 obj 10 0 obj The mechanism for nitration of benzene is in three steps. <>/XObject<>/ExtGState<>/ProcSet[/PDF/Text/ImageB/ImageC/ImageI] >>/MediaBox[ 0 0 720 540] /Contents 15 0 R/Group<>/Tabs/S/StructParents 1>> Nitration of Benzene. %���� 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 Toluene undergoes nitration to give ortho and para nitrotoluene isomers, but if heated it can give 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��͹� x�b```"a~���1�%�cNI��'��ѝ��sf������b�e:�"��x��e�q%��@Vp���-O����f�sV$Od�>S�v���&%�F! endobj <> endobj Consider the nitration of benzene versus the nitration of trifluoromethylbenzene and toluene (methylbenzene). Both π and σ transition states on the potential energy surface of the nitration of benzene with nitronium ion have been successfully optimized using unrestricted hybrid DFT procedure B3LYP with the triple-zeta 6-311G ** basis set without any 15 0 obj %PDF-1.4 %���� We see that the trifluoromethylbenzene reacts much, much slower (4 x 104 times slower) than benzene. 0000000016 00000 n endobj 0000002984 00000 n 5 0 obj endobj '� ���-9B�Ew���c���W��o9����?Nƨq�#MS�f8�y�6��7�cf����`䠟���Yq�K�>�o�L��J�!���F��X*8H��%�3��6�\7ov�ȲsRǔ�2�Ҭ�@�|B��`���h�Q�L��XA���E�\����c�TΤ�������5C쮆(Լ!C�T��+��p�^�W�N��t=����'���,.M�w��!q(|��1� 3 0 obj ]�,�\���w��oik #���_�,~�ϟX2������� �? 0000002739 00000 n AlCl 3 R Cl O R O 2. ��5Z|��$�u���=M���h�Qȟf�h}�̻�/�m]$I6Iw� B׬��a�a��h�\��+�ؑ��ۑ�,C��QF���*�S�bt�C?M�|��N�? endstream endobj Generation of electrophile <> 12 0 obj endobj 86 0 obj <> endobj Nitration of Benzene. 0000007095 00000 n Figure 1: The mechanism for the formation of a nitronium ion. Diprotonation. <>/ProcSet[/PDF/Text/ImageB/ImageC/ImageI] >>/MediaBox[ 0 0 720 540] /Contents 4 0 R/Group<>/Tabs/S/StructParents 0>> %%EOF 86 19 1 0 obj 88 0 obj<>stream endobj (�rng3%���?�M{:ǂ��A#�z�.� endobj Reaction type: Electrophilic Aromatic Substitution. The electrophile in the nitration of benzene is the + NO 2 (the nitronium ion), which is formed by protonation of HNO 3 by H 2 SO 4 (yep, sulfuric acid is powerful). NO 2 +) formed by the loss of water from the nitric acid It xref 0000006236 00000 n [ 11 0 R] �?�߇m{*��a�����^֤����������)M���^����j1�x=�9ڥ~�o�S�������E�)x!%j�a�&�Q�wZG �. 1. As the NO 2 + ion approaches the delocalised electrons in the benzene, those electrons are strongly attracted towards the positive charge.. Two electrons from the delocalised system are used to form a new bond with the NO 2 + ion. x��W��1�G�p���S �!6C� ��)��q{|ì�%�����nw��\���$Y�g]^��HQ|� �x�.�������FZ��m]�H��0J:��u]>�ˇ� ��+e��2���L���){+���%��Z��A%�?�3���q(��u��b��72�r$� Nitration General Reaction Mechanism E E (1) H E E H (2) + H+ Ca ta lys t R X R 1.

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