See the answer. evaluated Reaction of methyl benzoate with nitric acid to form methyl m-nitrobenzoate (Pavia 353). values cannot be derived. endstream endobj 77 0 obj <. Data compiled by: Coblentz Society, Inc. The aliphatic CH3 group shows stronger symmetric and antisymmetric stretches at 2960 cm−1 and 2870 cm−1. 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.

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with the development of data collections included in 0 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. 5. 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. Here's the actual IR spectrum of methyl benzoate. InChI=1S/C8H8O2/c1-10-8(9)7-5-3-2-4-6-7/h2-6H,1H3, National Institute of Standards and 105 0 obj <>stream View image of digitized We will use the melting point of the product to determine which isomer was formed in the reaction. The nitration of methyl benzoate could occur at the ortho, meta, or para position of the aromatic ring. nitronium ion (NO2 +). Technology, Office of Data

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Methyl 3-nitrobenzoate mp 78 oC M.W . %PDF-1.5 %���� Please check if I did it right. such sites. © 2003-2020 Chegg Inc. All rights reserved. Calculate the percent recovery from the recrystallization. Enter the desired X axis range

In this experiment, we used an EAS reaction to nitrate methyl benzoate. Do your observations match what you would expect for an electrophilic aromatic substitution of methyl benzoate? %%EOF NIST Standard Reference More information on the manner in which spectra

Data compilation copyright 1615.41 C=C stretch, aromatic. | Show work. uses its best efforts to deliver a high quality copy of the

The aromatic C-H stretch is usually weak and occurs at 3100-3000 cm−1. shall not be liable for any damage that may result from 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.

This IR spectrum is from the Coblentz Society's Your institution may already be a subscriber. Organic ChemistryI Lab EAS: Nitration Of Methyl Benzoate 4. 181.15 Methyl benzoate bp 198-199 oC M .136 5 d 1.09 HNO3, H2SO4 CO2CH3 CO2CH3 NO2. 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 Follow the links above to find out more about the data the by the U.S. Secretary of Commerce on behalf of the U.S.A. Is your IR spectrum consistent with the product formed? Privacy

In this experiment, we used an EAS reaction to nitrate methyl benzoate. in these sites and their terms of usage. Interpret the IR spectrum of methyl nitrobenzoate at the indicated peaks.

1720.23 C=O stretch, conjugated ester. The purpose of the fee is to recover costs associated Assuming methyl benzoate is the limiting reagent, calculate the percent yield of the reaction using the crude weight. Explain your answer. carefully selected solvents, and hence may differ in detail Methyl m-nitrobenzoate comprises a nitro group, or -NO2, and a methyl ester group, or C(=O)-O-CH3, attached to a benzene ring.

The overall reaction is depicted in Figure 1. Notice: Concentration information is not Institute of Standards and Technology, nor is it intended to imply

click the mouse on the plot to revert to the orginal display. 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. methyl ester, the methyl comes before the benzoate.

NIST subscription sites provide data under the in this collection were collected can be found spectrum (can be printed in landscape orientation). 2. (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). h�b```�*� ��ea�� o�T��0((�}p[CDCD8�� Ҽ@�`T�?����)lj=bИ�`�p��[��.�[< ű�����e�0 � 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! 2964.93 Sp3 C-H stretch. that these items are necessarily the best available for the purpose.

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. Figure 1. Was your product pure? collection were measured on dispersive instruments, often in View desktop site, Organic ChemistryI Lab EAS: Nitration of Methyl Benzoate 4. infrared reference spectra collection. Select a region with data to zoom. Go To: Top, Infrared Spectrum, References. However, NIST makes no warranties to that effect, and NIST

and Informatics, NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data), Modified by NIST for use in this application, evaluated 3 a. intended to imply recommendation or endorsement by the National errors or omissions in the Database. and HTML 5 enabled browser. here. from measurements on FTIR instruments or in other chemical

Explain how you made this determination from the melting point and 1H NMR data 3b.

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1.)

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Nitration of Methyl Benzoate Tare a 5-mL conical vial and add 0.21 mL of methyl benzoate to the vial.

3089.4 Sp2 C-H stretch. (hardcopy) spectrum. View scan of original Database and to verify that the data contained therein have This is what I have so far. jcamp-plot.js.

infrared reference spectra collection.

Step 1: Identify the absorption peak of the C=O group of the ester by its strong absorption between 1735 and 1750 1/cm. Nitration of Methyl Benzoate Alyson April Savattere PBT ASCP CPC AAPC Organic Chemistry 206 Rhode Island College Providence Rhode Island 02908 asavattere_6375 environments. Cap the conical vial The following components were used in generating the plot: Additonal code used was developed at NIST:

Go To: Top, References, Notes Data compilation copyrightby the U.S. Secretary of Commerce on behalf of the U.S.A.All rights reserved. h�bbd``b`Z$�� �^$XB@D�`n)�b��1w��i�Ė��p�XJ@�f8#�m ����\�?��/ t�#

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.

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76 0 obj <> endobj Notice: This spectrum may be better viewed with a Javascript The overall reaction for the nitration of methyl benzoate. Which of the three possible regioisomers was fomed? available for this spectrum and, therefore, molar absorptivity The nitration of a benzene ring is an electrophilic aromatic substitution reaction, andits general mechanism is All rights reserved. jcamp-dx.js and on behalf of the United States of America. Standard Reference Data Act.

Data Program, but require an annual fee to access. The nitronium ion temporarily interrupts ring resonance and reacts with electrons in a pi bond to form a carbocation intermediate. HTML 5 canvas support. Notice: Except where noted, spectra from this