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1 Question 1. NMR Basics. (20 points) (a) Indicate schematically the magnetic moments of individual nuclear spins (at least 10) as arrows for the following situations. Assume as always that the external magnetic field is pointing straight up (z-direction). (8) After the sample is placed in the magnetic field. (But no pulses as yet). After one 90 pulse. After the experiment and, more precisely, after ten periods of T 1 after one period of T 2 seconds passed. seconds passed. more up than down isotropic equal numbers up & down anisotropic back to start as on very left starting to relax, between situations 1 and 2 (b) Schematic of the Zeeman levels for an AX-pair of H-nuclei with δ(h a ) << δ(h x ). (6 points) On the left: Draw the Zeeman levels for H a and H x assuming that J(H a,h x ) = 0. On the right: Draw the Zeeman levels for H a and H x assuming that J(H a,h x ) 0. E J(H a,h x ) = 0 H X E J(H a,h x ) 0 0 H A 0 (c) Solvents (6 points) Multiplicity depends on the number of equivalent neighbors n and their nuclear spin I and the multiplicity is given by 2 n I+1. For spin I = ½ nuclei, this formula simplifies to the n+1 -rule. Acetone-d6 (you observe Acetone-d6) C couples to n =_3_ equivalent D-atom(s) with nuclear spin I = 1. Multiplicity of 13 C signal: = 7 DMSO-d6 (you observe DMSO-d5) H couples to n =_2_ equivalent D-atom(s) with nuclear spin I = 1. Multiplicity of 1 H signal: = 5-1-
2 Question 2. Chemical Shifts & Increment Systems. (20 points) 1 H- and 13 C-NMR of Vanillin (from SDBS, requires the book by Pretsch et al.) The structure of vanillin is shown and the chemical shift data are taken from the SDBS database. Using the book by Pretsch et al., find the base value for the chemical shift of an aromatic C-atom C x, locate the Z i - values and provide them in the table below. Do the same for the attached H-atom. Make sure to indicate the i of the Z i -values (where the underline is shown). Then make the additions to obtain the calculated chemical shift, assign the measured peaks and enter their chemical shifts in the respective row, and, finally, compute the difference between calculated and measured values. H-NMR Chemical Shifts (ppm) 3.959, 6.39, 7.047, 7.42, 7.42, C-NMR Chemical Shifts (ppm) , , , , , , , H 3 C HO O Cx Hx H O C x H x Base = ppm Z 2 (OMe) = Z 3 (OH) = 1.4 Z 2 (CHO) = 1.2 Base = 7.26 ppm Z 2 (OMe) = Z 3 (OH) = Z 2 (CHO) = 0.61 Calculated: Measured: Deviation: Row 2, 8 points: One point for each base value and each pair of subscript & Z-value. Row 3, 4 points: Correct addition. Row 4, 6 points: Correct assignments of the measured shifts to C x and H x. Row 5, 2 points: One point for each correct error calculation. -2-
3 Question 3. Nuclear Overhouser Effect (NOE). (20 points) alpha CH (1) (2) (3) (4) (5) (6) (7) (8) Carbon T 1 NOE 13 C-Int. H att. (sec) alpha , ipso , ortho , meta , para This is all about toluene. The numbering of the atoms is shown in the drawing. The T 1 and NOE data are taken from the textbook; the intensities are from the toluene spectrum in the SDBS database. (a) The SPIN - LATTICE relaxation times T 1 are given in column (2). In general, the shorter the relaxation time T 1, the higher the signal intensity. In column (3) provide the rankings for the C-peak intensities that you would expect based on T 1 alone (from 1 to 5, 1 highest intensity, 5 lowest intensity). (8 p.) (b) The NOE factors are given in column (4). The factors specify the amount of the increase of the 13 C-NMR signal that is achieved when the H-nuclei are irradiated. In column (5) provide the rankings for the C-peak intensities that you would expect based on NOE alone (from 1 to 5 as above). (5 points) (c) Measured intensities with rankings are listed in columns (6) and (8). State whether the intensities are dominated by T 1 or by NOE. Provide a very brief explanation as to why this is so; a few good words suffice! (4 p.) Neither. In this specific case it looks like it goes more by NOE but even here that does not really hold. Without decoupling, T 1 matters. With decoupling, it s more complicated because now T 1 as well as other relaxations (w2) matter. (d) The NOE for the ipso-c is not zero! The NOE effect of the CH 3 -carbon is much less than 2. The CH-carbons have the best NOEs. Does it matter for a carbon s NOE how many Hs are attached? Does it matter for a carbon s NOE whether any H is directly attached? What then is required for a C-atom to show NOE? (3 p.) It does not matter how many Hs are directly attached! -- It does not matter whether any H is directly attached! -- The only thing that matters is that there are some Hs not too far away from the C that wants to benefit from the NOE. -3-
4 Question 4. Valine, (H 3 C) 2 CH CH(NH 2 )COOH. (40 points) 1 H-NMR: MHz, 0.04 g : 0.5 ml D 2 O SDBS No C-NMR: MHz, g : 1.5 ml D 2 O SDBS No
5 (a) In the spectra of DL-valine (racemic) on previous page, assign as many peaks as you can. (20 points). (b) State how many signals there are in the 1 H-NMR spectrum of pure L-valine, state the multiplicity of each of these signals, and state who causes each signal. Diastereotopic methyl groups in the ipr-group: two overlapping doublets Unique H at alpha-c of amino acid: doublet with 3 J Unique H in the ipr-group: (qq with almost equal 3 J values; essentially a septet) and t due to 3 J (c) State how the 1 H-NMR spectra of pure L-valine and of pure D-valine differ. They are the same. The signals of the methyl groups of the propyl group switch places in the spectrum. (d) State how many signals there are in the H-decoupled 13 C-NMR spectrum of pure L-valine and explain why. Diastereotopic methyl groups in the ipr-group: two signals CH-carbon in the the ipr-group CH-carbon in the alpha-position of the amino acid Carboxylate-C Total: 5 signals (e) State how the H-decoupled 13 C-NMR spectra of pure L-valine and of pure D-valine differ and explain. They are the same. The signals of the methyl groups of the propyl group switch places in the spectrum. (f) State how many signals there are in the H-decoupled 13 C-NMR spectrum of 90% 15 N-enriched, enantiomerically pure L-valine, and state the multiplicity of each signal. I( 15 N) = ½ CH-carbon in the alpha-position of the amino acid shows as doublet because of coupling with 15 N. Everything else as in (d). -5-
Z 2 (OMe) = Z 3 (Cl) = 1.4. Calculated: Measured: Deviation:
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