Copyright for NIST Standard Reference Data is governed by Data compilation copyright However, NIST makes no warranties to that effect, and NIST infrared reference spectra collection. 3089.4 Sp2 C-H stretch. View image of digitized 105 0 obj
<>stream
on behalf of the United States of America. that these items are necessarily the best available for the purpose. Calculate the percent recovery from the recrystallization. The interactive spectrum display requires a browser with JavaScript and Notice: Except where noted, spectra from this The purpose of the fee is to recover costs associated © 2003-2020 Chegg Inc. All rights reserved. & The electrophile in this reaction is the nitronium ion, NO2+, which is formed in situ by the reaction of concentrated nitric acid with concentrated sulfuric acid. Please check if I did it right. Discuss the major peaks present in your spectrum that support your answer This nitration of methyl Benzoate is a typical electrophilic aromatic substitution or EAS reaction. h�b```�*� ��ea�� o�T��0((�}p[CDCD8�� Ҽ@�`T�?����)lj=bИ�`�p��[��.�[< ű�����e�0 �
%%EOF
The aliphatic CH3 group shows stronger symmetric and antisymmetric stretches at 2960 cm−1 and 2870 cm−1. available for this spectrum and, therefore, molar absorptivity | uses its best efforts to deliver a high quality copy of the After determining the mass of the methyl benzoate place a magnetic spin vane in the vial and carefully add 0.45 mL of sulfuric acid to the vial containing the methyl benzoate. 0
nitronium ion (NO2 +). The overall reaction for the nitration of methyl benzoate. See the answer. In this experiment, we used an EAS reaction to nitrate methyl benzoate. Cap the conical vial InChI=1S/C8H8O2/c1-10-8(9)7-5-3-2-4-6-7/h2-6H,1H3, National Institute of Standards and endstream
endobj
startxref
The following components were used in generating the plot: Additonal code used was developed at NIST: here. Data Program, but require an annual fee to access. (hardcopy) spectrum. Follow the links above to find out more about the data 3 a. Enter the desired X axis range been selected on the basis of sound scientific judgment. Notice: This spectrum may be better viewed with a Javascript with the development of data collections included in Technology, Office of Data Data from NIST Standard Reference Database 69: The National Institute of Standards and Technology (NIST) Terms (e.g., SOLUTION (10% IN CCl4 FOR 3800-1350, 10% IN CS2 FOR 1350-450 CM, BLAZED AT 3.5, 12.0, 20.0 MICRON, CHANGED AT 5.0, 7.5, 14.9 MICRON, DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS). The electrophile in this reaction is the nitronium ion, NO2+, which is formed in situ by the reaction of concentrated nitric acid with concentrated sulfuric acid. Select a region with no data or The nitration of methyl benzoate could occur at the ortho, meta, or para position of the aromatic ring. The position of the ring that has the greatest electron density will be the most likely spot for the reaction with the electrophile to occur. collection were measured on dispersive instruments, often in the such sites. Discuss the major peaks present in your spectrum that support your answer This nitration of methyl Benzoate is a typical electrophilic aromatic substitution or EAS reaction. Explain your answer. Step 1: Identify the absorption peak of the C=O group of the ester by its strong absorption between 1735 and 1750 1/cm. 2. In this experiment, we used an EAS reaction to nitrate methyl benzoate. click the mouse on the plot to revert to the orginal display. Write out the mechanism for the formation of your product from methyl benzoate and the nitronium ion NO2 methyl mp: 96 °C methyl benzoate bp: 199.6 C methyl 2-nitrobenzoate 3-nitrobenzoate 4-nitrobenzoate mp: 78 °C methyl Melting point (MP) values Methyl 2-nitrobenzoate: -8 C Methyl 3-nitrobenzoate: 78 °C Methyl 4-nitrobenzoate: 96 °C mp: 8 °C Thank You in Advance! evaluated All rights reserved. Was your product pure? Institute of Standards and Technology, nor is it intended to imply All rights reserved. shall not be liable for any damage that may result from Privacy NIST subscription sites provide data under the 1720.23 C=O stretch, conjugated ester. Database and to verify that the data contained therein have Thank you! in this collection were collected can be found 1615.41 C=C stretch, aromatic. and Informatics, NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data), Modified by NIST for use in this application, evaluated 5. 181.15 Methyl benzoate bp 198-199 oC M .136 5 d 1.09 HNO3, H2SO4 CO2CH3 CO2CH3 NO2. spectrum (can be printed in landscape orientation). environments. jcamp-plot.js. Organic ChemistryI Lab EAS: Nitration Of Methyl Benzoate 4. Go To: Top, References, Notes Data compilation copyrightby the U.S. Secretary of Commerce on behalf of the U.S.A.All rights reserved. 76 0 obj
<>
endobj
We will use the melting point of the product to determine which isomer was formed in the reaction. This is what I have so far. Assuming methyl benzoate is the limiting reagent, calculate the percent yield of the reaction using the crude weight. in these sites and their terms of usage. values cannot be derived. © 2018 by the U.S. Secretary of Commerce 1.) Do your observations match what you would expect for an electrophilic aromatic substitution of methyl benzoate? This IR spectrum is from the Coblentz Society's 91 0 obj
<>/Filter/FlateDecode/ID[<835F7155C44D8F41879C52AA600A5CDB><1BFBB49EC86A1A428F950B55FD3FF617>]/Index[76 30]/Info 75 0 R/Length 80/Prev 61170/Root 77 0 R/Size 106/Type/XRef/W[1 2 1]>>stream
Data compiled by: Coblentz Society, Inc. methyl ester, the methyl comes before the benzoate. by the U.S. Secretary of Commerce on behalf of the U.S.A. carefully selected solvents, and hence may differ in detail
Figure 1. The nitration of a benzene ring is an electrophilic aromatic substitution reaction, andits general mechanism is Reaction of methyl benzoate with nitric acid to form methyl m-nitrobenzoate (Pavia 353). Standard Reference Data Act. Notice: Concentration information is not Explain how you made this determination from the melting point and 1H NMR data 3b. Which of the three possible regioisomers was fomed? Data Table of Nitration ml of methyl benzoate: 1.4 ml Mass of methyl benzoate: 1.512 g Crude Mass of nitro methyl benzoate: 2.0684 g Melting point of nitro methyl benzoate: 70 to 75 °C Recrystallized mass of nitro methyl benzoate: 0.9557 g Questions 1. HTML 5 canvas support. View desktop site, Organic ChemistryI Lab EAS: Nitration of Methyl Benzoate 4. The overall reaction is depicted in Figure 1. jcamp-dx.js and Nitration of Methyl Benzoate Alyson April Savattere PBT ASCP CPC AAPC Organic Chemistry 206 Rhode Island College Providence Rhode Island 02908 asavattere_6375 More information on the manner in which spectra intended to imply recommendation or endorsement by the National The aromatic C-H stretch is usually weak and occurs at 3100-3000 cm−1. 2964.93 Sp3 C-H stretch. Show work. Is your IR spectrum consistent with the product formed? Select a region with data to zoom. Methyl m-nitrobenzoate comprises a nitro group, or -NO2, and a methyl ester group, or C(=O)-O-CH3, attached to a benzene ring. and HTML 5 enabled browser. infrared reference spectra collection. NIST Standard Reference errors or omissions in the Database. Here's the actual IR spectrum of methyl benzoate. The nitronium ion temporarily interrupts ring resonance and reacts with electrons in a pi bond to form a carbocation intermediate. Go To: Top, Infrared Spectrum, References. Show work. Interpret the IR spectrum of methyl nitrobenzoate at the indicated peaks. Methyl 3-nitrobenzoate mp 78 oC M.W . from measurements on FTIR instruments or in other chemical h�bbd``b`Z$�� �^$XB@D�`n)�b��1w��i�Ė��p�XJ@�f8#�m ����\�?��/ t�#
%PDF-1.5
%����
Your institution may already be a subscriber. Nitration of Methyl Benzoate Tare a 5-mL conical vial and add 0.21 mL of methyl benzoate to the vial. View scan of original endstream
endobj
77 0 obj
<. Use or mention of technologies or programs in this web site is not