structures
.pdfProblem 129
3295
IR Spectrum
(liquid film)
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Mass Spectrum |
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UV spectrum |
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0.766 mg 110 mls |
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C1l |
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C1l |
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path length: 2.00 cm |
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solvent: methanol |
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C1QH1sN |
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II ,Il |
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13C NMR Spectrum |
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(20.0 MHz, COCI3 solution) |
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off-resonance decoupled |
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expansion x10 |
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TMS |
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proton decoupled |
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solvent |
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1H NMR Spectrum |
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exchanges |
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with 0 20 |
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o(ppm) |
218
Chapter 9.3 Problems in 20 NMR
Problem 294
The lH and l3C NMR spectra ofisobutanol (2-methyl-l-propanol, C4H IOO) recorded in CDCh solution at 298K are given below. The IH spectrum contains signals at
83.28 (HI), 2.98 (OH), 1.68 (H2) and 0.83 (H3) ppm. The l3C spectrum contains signals at 869.3 (CI), 30.7 (C2) and 18.7 (C3) ppm. On the facing page produce a schematic diagram of the COSY the C-H correlation spectra for this molecule showing where all of the cross peaks and diagonal peaks would be.
/
isobutanol
1H NMR Spectrum
(300 MHz, CDCJ 3 solution)
~pa",;o,
I
+
3.4 |
3:2 ppm |
expa~jl
Exchanges
with D20 1.8 1.6 ppm
I |
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• |
4.0 |
3.0 |
2.0 |
1.0 |
ppm |
13C NMR Spectrum
(75 MHz; CDCI3 solution)
solvent m
I |
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o ppm |
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Chapter 9.3 Problems in 20 NMR
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1H - 1H COSY Spectrum |
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(300 MHz, CDCI 3 solution) |
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------------!-._--!--------------------!------------!--------- |
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389
Chapter 9.3 Problems in 20 NMR
Problem 295
The lH spectrum of3-heptanone (C7H I40) recorded in C6D6 solution at 298K at
500 MHz is given below. The1H spectrum has signals at (50.79,0.91, 1.14, 1.44, 1.94 and 1.97 (partly overlapped) ppm. The 2-dimensional lH)H COSY spectrum is given on the facing page. From the COSY spectrum, assign the proton spectrum
i.e. determine the chemical shift corresponding to each of the protons in the molecule.
2 |
3 |
4 |
5 |
6 |
7 |
3-heptanone
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Chemical Shift (0) in ppm |
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390
Chapter 9.3 Problems in 20 NMR
IH COSY spectrum of3-heptanone (recorded in C6D6 solution at 298K, at 500 MHz).
2 |
3 |
4 |
5 |
6 |
7 |
391
Chapter 9.3 Problems in 20 NMR
Problem 296
The IH and l3C NMR spectra of 8-valerolactone (CSHg02) are given below recorded in C6D6 solution at 298K, at 600 MHz. The IH spectrum has signals at 8 1.08, 1.16,2.08, and 3.71 ppm. The l3C spectrum has signals at 819.0,22.2,29.9,68.8 and 170.0 ppm. The 2-dimensional IH_1H COSY spectrum and the C-H correlation spectrum are given on the facing page. From the COSY spectrum, assign the proton spectrum and use this information to assign the l3C spectrum.
3
o-valerolactone
:0;
a a
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1H NMR Spectrum |
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(600 MHz, c.o, solution) |
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Proton |
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392
Chapter 9.3 Problems in 20 NMR
1H -1H COSY Spectrum
(600 MHz, Benzene-Dg solution)
+ |
1.0 |
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2.0
1-
3.0
40
60
4.0 |
3.0 |
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ppm |
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393
Chapter 9.3 Problems in 20 NMR
Problem 297
The IH and BC NMR spectra of l-bromobutane (C4H9Br) are given below. The IH spectrum has signals at 8 0.91, 1.45, 1.82, and 3.39 ppm. The BC spectrum has signals at 813.2,21.4,33.4 and 34.7 ppm. The 2-dimensional 1H)H COSY spectrum and the C-H correlation spectrum are given on the facing page. From the COSY spectrum, deduce the assignment of the proton spectrum and use this information to assign the B C spectrum.
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4 |
3 |
2 |
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1-bromobutane |
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Proton |
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Chemical Shift (8) |
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Carbon |
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Chemical Shift (8) |
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in ppm |
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in ppm |
H1 |
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H4 |
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C4 |
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lH NMR Spectrum |
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(400 MHz, CDCI, solution) |
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iii |
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1.8 1.6 1.4 |
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( |
i |
9 |
8 |
7 |
6 |
5 |
4 |
3 |
2 |
ppm |
|
13C NMR Spectrum
(100 MHz, CDCI, solution)
DEPT CH,. CH,t CHt
proton decoupled
•
I
120 |
80 |
40 |
o |
ppm |
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394
3.0
-- I
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3.0 |
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4.0 |
395
Chapter 9.4 NMR Spectral Analysis
Problem 326
A 200 MHz 'H NMR spectrum of a 5-proton system is given below.
(a)Draw a splitting diagram.
(b)Analyse this spectrum by first-order methods, i.e. extract all relevant coupling constants (J in Hz) and chemical shifts (0 in ppm) by direct measurement.
. (c) Justify the use of first-order analysis (see Section 5.6).
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2H |
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2H |
1H |
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990 |
510 |
490 |
110 |
90 |
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Hz from TMS |
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Hz from TMS |
Hz from TMS |
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437