NMR and other Instrumental Techniques in Chemistry and the proposed National Curriculum.

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1 NMR and other Instrumental Techniques in Chemistry and the proposed National Curriculum. Dr. John Jackowski Chair of Science, Head of Chemistry Scotch College Melbourne

2 Whilst not much of the content of Chemistry can change significantly, the use of ICT resources has moved ahead in gigantic leaps and bounds. I am not suggesting that simulation replace experimentation but it is my contention that the range of instruments and resources in 2011 should be able to deliver a much more stimulating and exciting brand of Chemistry in the greater part of the 21 st century.

3 In the first draft, teachers were to be given a choice of two techniques Colorimetry Chromatography including GLC/HPLC Atomic Absorption Spectroscopy (AAS) UV-Visible Spectroscopy Mass Spectrometry (MS) - molecular Nuclear Magnetic Resonance (NMR) Infrared Spectroscopy The experience of Chemistry teaching, learning and assessment in Victoria since 2008 would lead me to believe that we would be doing our students a great disservice if this narrow selection is maintained. We need to prune elsewhere and continue with the push for the areas involving instrumentation.

4 Why: (not in any particular order) Detective aspects of Chemistry excite and interest students Higher Level Thinking Skills Development of ICT teaching resources and the associated interactivity leading to more student centred learning with the teacher as a facilitator. Cheaper and simpler instruments on the market Greater access to tertiary institutions and their facilities; Mobile instruments - incursions already happening The lack of safe and relatively easy organic pracs. Not much point in learning about a multitude of functional groups at the expense of the instrumentation Why not? Too much in the courses already not enough time same old story Teachers do not like too much change Substantial PD and development of resources.

5 The New Year 12 Chemistry Study Design in Victorian school from the beginning of This included a more extensive organic section including production of synthesis of medicines eg aspirin, biological applications including DNA and proteins as markers for disease and production of biofuels. Structural analysis sections new to the course included 1 H and 13 C NMR Infrared Mass Spectrometry of molecules

6 April 2007 VCAA Bulletin NMR involves the interaction of nuclei(not electrons) with electromagnetic radiation. Students should appreciate the information that can be obtained from chemical shift measurements and the number of peaks in a spectrum. While an understanding of the theory of spin-spin coupling is not expected, students should be able to recognise equivalent and non- equivalent atoms in a molecule and apply the n+1 rule in simple cases. For example, they should be able to predict that the 1 H NMR spectrum of CH 3 CH 2 COOH would consist of a quartet, a triplet and a singlet. Only proton decoupled 13 C NMR spectra are studied and unlike 1 H NMR, the peak areas are not used to determine the number of C atoms present and no splitting patterns are present.

7 Marino Dereani Eutectic Educational Mob:

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9 VCAA 2008 MC Question 5 The disease sickle cell anaemia is marked by the presence of an abnormal protein in the blood of people with this disease. The sixth position in the normal protein chain is occupied by the amino acid, glutamic acid. The sickle cell protein chain has the amino acid, valine, in the sixth position. This is the only difference between the two protein chains. A section of each protein chain containing glutamic acid and valine is shown below It is possible to determine the molecular mass of these proteins in a mass spectrometer. It is also possible to record their 1 H NMR spectra. Which one of the following alternatives is correct?

10 M= = 73 M= = 43 Glutamic acid Valine molecular mass 1H NMR spectrum A. Sickle cell protein chain has the greater molecular mass. Both protein chains have the same 1 H NMR spectrum. B. Sickle cell protein chain has the greater molecular mass. The protein chains have different 1 H NMR spectra. C. Normal protein chain has the greater molecular mass. Both protein chains have the same 1 H NMR spectrum. D. Normal protein chain has the greater molecular mass. The protein chains have different 1 H NMR spectra A.4 B. 14 C.13 D. 69

11 2008 Section B Question 4 A mixture contains several different organic liquids all of which boil at temperatures greater than 50 C. The compounds present in the mixture are separated. Three of the compounds, compounds X, Y and Z, are analysed as follows. Compound X is vaporised. At a temperature of 120 C and a pressure of 115 kpa, a g sample of the vapour occupies 124 ml. a. Calculate the molar mass, in g mol 1, of compound X. (2 marks) Av % b. Compound Y is an alkanol of molecular formula of C 4 H 10 O.

12 b. i. In the boxes below, draw the structural formulas, showing all bonds, of the four possible alkanols with a molecular formula of C 4 H 10 O. Alkanol 1 Alkanol 2 four C environments four C environments Alkanol 3 Alkanol 4 three C environments two C environments OH must be on the end

13 Compound Y shows 3 lines in the 13 C NMR spectrum and undergoes reaction with Cr 2 O 7 2 (aq) in acid to produce a carboxylic acid. ii. What evidence about the structure of Y can be gained from this information? Evidence from 13 C NMR spectrum Evidence from reaction with Cr 2 O 7 2 (aq) in acid solution iii. Based on the above evidence, identify compound Y by circling the structural formula in part i. that corresponds to compound Y writing below the systematic name of compound Y = 8 marks 4b Av %

14 Compound Z has the molecular formula C 5 H 10 O and shows a strong band in the infrared spectrum at about 1700 cm 1. The 1 H NMR spectrum of compound Z is given below. Adjacent to CH3 Adjacent to CH2 c. i. What information about the structure of Z can be deduced from the above spectral data? From IR data C= O From 1H NMR Two H environments ii. Draw a structure for compound Z that is consistent with the spectral data. 4c. Marks Av % = 3 marks

15 200 9 A B C D Question 20 The separation and identification of proteins that can be used as disease markers is an exciting area of research. Researchers must separate and identify proteins that could be used as disease markers from the many thousands of proteins that exist in our bodies. Which of the following sequence of techniques could be used to i. separate these molecules, then ii. accurately determine their molecular mass, and then iii. determine their molecular structure. A. NMR spectroscopy, followed by mass spectrometry, followed by HPLC B. HPLC, followed by mass spectrometry, followed by NMR spectroscopy C. HPLC, followed by infrared spectroscopy, followed by mass spectrometry D. mass spectrometry, followed by HPLC, followed by infrared spectroscopy A B C D no resp

16 2009 Question 5 The structure of an organic molecule, with empirical formula CH 2 O, is determined using spectroscopic techniques. The mass spectrum, infrared spectrum and 1 H NMR spectrum for this molecule are given below.

17 Use the information provided by these spectra to answer the following questions. What is the molecular formula of this molecule? How many different proton environments are there in this molecule? 2 different 1 H environments Marks 0 1 A % Marks 0 1 Av % c. Draw the structure of the unknown molecule, clearly showing all bonds. 1 mark 1 mark 1 mark d. Explain how the structure of the compound you have drawn in part c. is consistent with its IR spectrum. Marks 0 1 Average Broad peak at (cm -1 ) indicates O-H (acid)* bond. % mark e. Name the compound you have drawn in part c. Marks 0 1 Av % Marks 0 1 Av % In Section B, students overall performance was the best on Question 5. The majority of students were clearly comfortable with the interpretation of mass, NMR and IR spectra and linking together the information to deduce a molecular structure. 1 mark Total 5 marks

18 2010 Question 2 The molecular formula of an unknown compound, X, is C3H 6 O2. The infrared 13C NMR and 1 H NMR spectra of this compound are shown below.

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20 The 1H NMR spectrum data is summarised in the following table. ii. Draw the grouping of atoms that would give rise to the triplet and quartet splitting patterns. a. Using the Infrared absorption data on page 7 of the Data Book, identify the atoms and the bonds between them that are associated with the absorption labelled A on the infrared spectrum. b. How many different carbon environments are present in compound X? 1 mark 1 mark c. How many different hydrogen environments are present in compound X? 1 mark d. i. The signal at 1.3 ppm is split into a triplet. What is the number of equivalent protons bonded to the adjacent carbon atom?

21 2010 Question 2 The molecular formula of an unknown compound, X, is C3H6O2. The infrared 13C NMR and 1 H NMR spectra of this compound are shown below. C = O Marks 0 1 Av %

22 Three C environments Question 2b. Marks 0 1 Av % Three adjacent H atoms ie CH3 Two adjacent H atoms ie CH2 2di. Marks 0 1 Av % Three H environments Marks 0 1 Av % One isolated H atoms Question 2dii. Marks 0 1 Av %

23 2011 Question 19 Petrol is a mixture of hydrocarbon molecules varying in size from six to ten carbon atoms. Forensic investigators suspect that traces of a substance found at a suspicious fire could be petrol that was used to start the fire. Which one of the following techniques could best be used to identify the substance? A. NMR spectroscopy B. UV-visible spectroscopy C. atomic absorption spectroscopy D. gas chromatography followed by mass spectroscopy Correct Ans: D

24 2011 CH 3 CH 2 + Almost equal % as peak heights at 108,110 almost same height

25 Adjacent to CH3 Adjacent to CHBr2

26 Structure 1 has two H environments Structure 2 has one H environments Ans: Structure 1 At 2.5 ppm, protons are adjacent to CHBr2 At approx 6 ppm, proton is adjacent to CH3

27 SIMPLY NMR Version 2 Software for teaching NMR Simply NMR 2 is the specialty software package of choice for teaching and learning about Nuclear Magnetic Resonance (NMR) spectroscopy at a high school standard. It serves a dual role firstly a teaching support medium and secondly a student centered tool. The package has been engineered using the latest technologies with a focus on high quality. Its design demonstrates many features which provide an interactive diagnostic approach. The package has been custom built for teaching NMR in the Victorian VCE Chemistry course and can be used in association with the International Baccalaureate (IB) course. The product itself is built on a robust development platform and will provide you the teacher with a top quality support tool for teaching about NMR. It can be used as a template for assignment work, revision and exam preparation. Simply NMR 2 is a must have product.

28 Enthuse and stimulate your students by using Simply NMR 2 with its distinct diagnostic approach. Create an atmosphere of investigation in your classroom by utilizing cutting edge technology and thereby guiding your students into the world of chemical structures and how to analyse them by MNR spectroscopy. Simply NMR 2 is a genuine new generation approach to using technology in the modern classroom. Pricing The package is priced as a minimal 3-year contract which will be extended annually thereafter. The terms of contract include a compulsory 1 st year payment of product license. This is a once only payment in the 3-year period. The subsequent 2yr period will be controlled by an annual student subscription fee based on the student numbers. Use of Simply NMR 2 will be made available by internet connection and by school hardcopy. On entering the contract each school will be given access to the online facility and will be provided with a hardcopy of the program. It is advised that the hardcopy should be installed on the school network for backup purposes and student access both on and off campus. If you have any further enquiries about the package please contact Eutectic Educational on or by on Quotes will be provided on request.

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