experiment 35 bromination of vanillin

0000006740 00000 n � 9�JErF�(in NWFD����[�tj�Yk�.���� h)�":L��n���g�7�tO����H�8�T�7E�0� �E\�{ȳ���&�/ڀ �{���dI���L$��;�d�k���} Hn�Y[bs�a�D��-Z3��ت �{�~lV�D�@?�Rj�f�m�e=> #���h��/���E=8�S�bsB+�T>p�����n�ɿK�����lׁ:��67�McҜ#�4fC&�� _���������t�������/�cz��x;JN�Ѥ�s����kpz|�9������M��^�����+T�mQ���ܞs�1%�*�P�=6#�����q�Qi̷@��� aN[���C0o ���|5����'�t��(� Z��|�#J:�����DQ� Ɍf���-7*PZ�=a�n�\H����$%גY�y3�s�[؜:KԷ3�~+Q�X�2����1u��DO�ˈ�ȧ��u�T� �>U-^J2�י� P ���D�d=� �{w� oF���VT�̽�^�t5��iNEh&�>iF�>s���`�##B����)���gDF��҂�d�® e���Am�o�,���\��l��:��w�:��b��)��gw��P]�p{8��v�o1j?W„�0�m�K�~s5Y�H,V�i+� �Y� H�]Yb)�NJ,�P���u ��~�9�� 0ֺ�� �`��EYM ��X�@ԄFאz� ~f��R!i �qE�) �45Ɗ"�"�w�.�a��A�V6�$��1K(A LRk���|[&�$�E�T�Ijȕ|�&a���\iR6�ɛ"M*�&�k�)Ҥ"lRY��q a� Density = 0.789 g/mL Figure 1. �i�z�cHG�T�)M�B��8�S�g�b�y��f�D�L��2�t���n��V�^t����ӋN_���f��[}���I(Q�/�mi1�6�ئ�濾�ڜ����1��ʵ8��w�2�b3*�ߌ�idfS�>�a6���W,߄o�g�6/�sCl�8� �����3��������B �v�����z�����f�N6 ���z�"�P��k"� LXebp�]�s�]B�a��mώ��#;�+8����#TK�'�"�A�d�|���;jk)���^T/a���Υr�X1������v��p��B��������UB��8,�&r�qO8Ǎ���4y�$UB:�t�}^6/q��v�BNf�̭=lo�~P]��P�i�;W�ɒ�Fp�ii2�f��I_��R!�8.oG�wN���i�`zD�NK^�! These... ... 1.) Aniline and acetanilide contain amine groups, which are electron-donating. 0000000656 00000 n ��?�¢��X��BࠥьC%�5ی�|���EF=3�VR�@�����4A��P}�2�. The diffusion pump was connected to the water supply and turned on to 90 V. The cold trap of the apparatus was filled with Liquid nitrogen every hour of the experiment. MM = 46.07 g/mol B In electrophilic aromatic substitution, (EAS for short), the rate determining step is the first step of the reaction. The reaction is an example of an electrophilic aromatic …


Phenol contains a hydroxyl group. 0000002601 00000 n 0 The reaction rate with the aromatic ring depends on its substituents. The melting point ranges of the final products will be taken in order to determine their identities and reactivity. This step is the most important factor that decides which substituents make benzene react faster.

xref First is the substitution by bromination. Human errors Nitrophenol contains two substituents, one of which is a nitro group which is electron-withdrawing. Nitric acid

Bromination of Vanillin to 5-Bromovanillin (5) Dissolve 228 mg (1.50 mmol) of vanillin in 3 mL of meth- anol and 3 mL of water in a 50-mL Erlenmeyer flask. Part I (nitration of methyl benzoate) was carried out by Jenny.

...Electrophilic Aromatic Substitution :�yϜY��mT3�cG���~}&���"����=ʽ@Be*�;�7���CjB^+m/����&���&�dA�0J���@'9 D1�Ft400(ut���B@������i~ ���� Y&g��t�0=�J`�����۲���)��i�A����N�L@l ĺG�AN "%� \ Bm Please join StudyMode to read the full document.

Second is the solvent effect which is dealing in the nature of the solvent. + E+ Experiment No.1, Submitted on August 6, 2011 at N402.

(oC)Methyl benzoateC8H8O2136.161.094-15198-200Methyl 2-nitrobenzoateC8H7NO4181.141.289-13104Methyl 3-nitrobenzoateC8H7NO4181.14-78-80289Methyl 3,5-dinitrobenzoateC8H6N2O6226.14544-106-109-Methyl 4-nitrobenzoateC8H7NO4181.15-94-96-1,4-DimethoxybenzeneC8H10O2138.161.0555-582131,4-Di-t-butyl-2,5-dimethoxybenzeneC16H26O2250.37-104-105-2-methyl-2-propanolC4H10O74.12-25.482.4Hazard Concentrated sulfuric acid and nitric acid are... ...Factors Affecting the Relative Rates of Electrophilic Aromatic 0000000016 00000 n endstream endobj 60 0 obj<> endobj 61 0 obj<> endobj 62 0 obj<>stream �c�6R�uH�/�~�I[��K�l�#ȃ��#-7�@��D)X�ʳ"�v��9�MS�δ�u1��;;��5�y��`��Vo>�Z?d���V���nJA���#�}��xh!�J�N�π�ZF���W+�(Fu�ZY>���`��¾�X�G �@V"Q� x�ӊzS�=CvuU�b�z�"�ˏ�5���������y���9�=�O�k������ Z���գ>J��H�6r����.Ķ��#�[*f AROMATIC COMPOUNDS ARE ALWAYS FOLLOWS THE SUBSTITUTION REACTION BECAUSE OF THE STABILITY OF THE BENZENE RING. 3���r�2�=��`�o͝X5xw&j)�;�z�Ī�U�>v���b�wB.e���I��0��:*�s٬2��e�p��d����ȪR�$W��r��U"�7��q��ɻ���1�NQtv��3�u�. The substituents being tested are aniline, anisole, acetamide (acetanilide), and phenol. 46 18 Bromination is the reaction that will be carried out. The substituents being tested are aniline, anisole, acetamide (acetanilide), and phenol. The para form was separated from the ortho form based on solubility properties using recrystallization techniques. @ �� Date Performed: February 27, 2015 the ratio between vanillin and 5-bromovanillin is 1 : 1. theoretical moles 5- bromovanillin = 0.00200 Melting point = 215-217°C bromobenzenes. ����]�E�9��j[1�MK��w8�v�7���4Oåt��{�>ptd[�꺵�̀��F�����2�� �/��b�_� �¸�*�"$���[��"�4UlWk�A�H����JH�MJ��pj;���+����

p-nitroacetanilide 0000007703 00000 n

E The Knudsen cell was inserted into the sample tube and the closed end of the sample tube was placed into the prepared water bath. Aromatic electrophilic substitution (Ar-SE) Reactions In this experiment a high vacuum sublimation was performed to determine the vapor pressure and finally the enthalpy of sublimation of Vanillin and o-Vanillin. Synthetic equations: Boiling point = 78°C It is predicted that substitution order from most to least reactive should be aniline, phenol, anisole, and acetamide. H��W�z�F��S���g4j��;c[�X�w2��B��錐�$��c$ﶏ��[}� {l9ߌ�h�����������������C����k��" ���f"����텆/4U�4�1�R:gFLiDW=[�#�RM9�����U�O;��-I�E���Hӂ��h�?F)��hC��(�ӏȇ�(IH�H�g E H 3 0 obj Hazards: oxidizing liquid, corrosive to metals and skin, serious eye damage


An electrophilic aromatic substitution reaction is the attack of an electrophile on an aromatic ring substituting for a proton. 46 0 obj <> endobj

The special reactivity of aromatic systems towards electrophiles arises mainly from two factors: the presence of π electron density above and below the plane of the ring - making it nucleophilic, and the drive to regain the aromatic character by opting for substitution as opposed to a simple addition reaction.


16 x x x Probably needs further tweaking. Regioselectivity and the rate of electrophilic aromatic substitution are affected by the substituents attached to the original benzene. <<810BC2E5DC1BDB4EA7DD177CB9AB4C8C>]>> MM = 63.01 g/mol %���� Ethanol Crystallization was used to purify the product. Density = 1.480 g/mL 0000001502 00000 n DIFFERENT REACTION WILL YIELDS TO A CONCLUSION OF WHAT IS/ARE THE FACTOR/S OF ELECTROPHILIC SUBSTITUTION ON AN ORGANIC COMPOUND – AROMATIC COMPOUNDS. Figure 2. The tube with the O-ring was connected to the sublimation apparatus. Some common electrophilic aromatic substitution reactions are: halogenation, nitration, sulfonation, Friedel-Crafts Acylation and Friedel-Crafts alkylation. 0000003346 00000 n

Hazards: corrosive to metals and skin, serious eye damage Abstract

0000001181 00000 n Preference towards addition reactions in the case of alkenes and substitution in the case of aromatic compounds becomes evident if we analyze the energy profiles of these reactions (Figures 1 and 2). o-nitroacetanilide School of Chemical Engineering and Chemistry, Mapua Institute of Technology, Intramuros, Manila, Philippines <>/ProcSet[/PDF/Text/ImageB/ImageC/ImageI] >>/MediaBox[ 0 0 612 792] /Contents 4 0 R/Group<>/Tabs/S/StructParents 0>> 12 x x x Bromination with Br2 works fine but questions about product structure remain when pyridinium tribromide used. The mixture was carefully swirled in an ice bath to ensure... ... Electrophilic Aromatic Substitution: Bromination of Aromatic Compounds Procedure trailer <> Under a fume hood, add several drops of bromine-water reagent slowly with swirling until the reddish brown color of bromine remains in the solution and no more product forms. 4�U�ˣg�t]p��Ë�0 th�f 63 0 obj<>stream ��^��@��D�I%�t�F+"�bN{�g�z+��j�; %PDF-1.4 %���� Uncontrolled environmental factors such as light and temperature.

Boiling point = 290°C 0000003847 00000 n endobj 13 x x x 14 x 15 x Experiment has been performed by students in our lab but untested changes have been made since then.

Objective + HB+ ;]�]�_R��ѼP����xw�zHQ$ERb�߲/������_�d�.�������ך]}:?��?��eNn=��r~V���������E�Lm��x���K�ln��}�7-�p�o:��_�C�6�ؿ�ʅ���{�~������^�,(O/�В+�J�~�f���+�������E��~9�6qaj.m��H+��Sڷ�����grs`��{S���]��o�bƞ�Jh:~b�]�x����H��R)sV�Zvu�R��ⲙ��c�II��'�P�ޘ����VB����-���{��} ��i�G�SO|����`��;�$]��8���^��d,�V�xk�

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The mechanism of electrophilic aromatic substitution involves an initial rate determining interaction of the π system with the electrophile to give a benzenonium ion intermediate (σcomplex or wheland complex), which undergoes a rapid de-protonation by the base in the second step to restore aromaticity (Figure 3). MM = 98.08 g/mol This reaction allows for the introduction of other functional groups onto the aromatic ring. Physical Properties & Hazards of Reagents/Products: (all taken from Sigma-Aldrich website) Each of the compounds contains different types of C-H bonds. Chlorobenzene contains chlorine, which is electron-withdrawing.

Justiniano, Priscilla Raiza N. 0000004349 00000 n Having this division in the experiment one, we can now conclude that substituent in substitution, the... ...Engineering Chemistry III MM = 18.02 g/mol The electrophilic aromatic substitution reaction is the attack of a benzene ring on an electrophilic species resulting in the substitution of a proton with a functional group.

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